The Ultimate Guide to the 59 Best Things to Do in Portland, Maine

The Definitive Handbook to Portland, Maine: Uncovering 59 Must-Experience Activities in the City

Looking for things to do in Portland, Maine? I’ve got you covered. From lighthouses to breweries, here are the top 59 experiences in this charming coastal town.

I visited Portland in October and I completely fell in love with this little coastal town. I found myself exploring every nook and cranny as much as I could. And guess what? For a small town, it turns out that there is a lot to do in Portland, Maine.

Between exploring breathtaking natural beauty, strolling down historic streets, and checking out cultural landmarks, there is something for everyone here. But you’d hardly know it since most of Portland’s awesome activities are hardly ever talked about!

So, if you’re visiting Portland and looking for some fun things to do, you’re in the right place. From diving into culture and history at museums, taste testing at the many breweries, and exploring Portland’s famous lighthouses, I’m going to go over the 59 very best things to do in Portland, Maine.

59 Best Things to Do in Portland, Maine

Discover Portland, Maine’s authentic charm through the 59 best things to do in Portland, Maine. 

Explore the Historic Old Port District

Portland’s Old Port is a charming blend of cobblestone streets, 19th-century brick buildings housing posh boutiques and art galleries, and renowned restaurants and bars. Whether you’re visiting Portland in the summer, winter, spring, or fall, this historic neighborhood is a must-stop location.

1. Portland Freedom Trail

Explore the Portland Freedom Trail. It’s a free and self-guided tour highlighting 13 significant sites commemorating 19th-century Black Mainers who played pivotal roles in the fight against slavery.

The trail unveils the local Underground Railroad’s clandestine routes. As you go from milestone to milestone, you’ll wander through historic wharves, churches, private homes with hidden passageways, and businesses that ingeniously distributed anti-slavery pamphlets alongside their products. 

This immersive experience sheds light on the incredible journey of formerly enslaved individuals seeking freedom in Maine and Canada.

This is an awesome free activity in Portland.

2. Shop til you drop on Exchange Street

One of the best things about exploring a historic town is wandering through the many shops and boutiques in the city’s downtown area. Portland does not disappoint when it comes to charming little stores featuring unique souvenirs that are so tempting to purchase and take home. I myself ended up with a pair of jade and raccoon teeth earrings (I made sure they were ethically sourced) from the Maine Souvenir Shop. 

Indulge in a shopping extravaganza on Exchange Street in Old Port, Portland. Lined with eclectic boutiques, this vibrant street invites you to discover unique treasures, from fashion finds to locally crafted art. 

3. A Walk Through Time Tour in Portland

A Walk Through Time Tour is a mesmerizing exploration of Portland’s rich history. Our tour was led by a seasoned local guide named James who has been living in Portland for 30 years.

This immersive walking tour weaves tales of Portland’s past as you traverse the Old Port, downtown, and waterfront areas. 

Highlights include exclusive access to the Customs House, glimpses into historic sites like Hendry Wadsworth-Longfellow’s home, and engaging narratives about Portland’s fascinating history.

➡️ To see my detailed review of my experience on the A Walk Through Time Tour in Portland, Click Here.

4. Audio Guided Walking Tour from Old Port of Portland, Maine

Explore Portland, Maine, at your own pace with the Audio Guided Walking Tour from Old Port. 

This self-paced adventure offers the freedom to discover the city’s historic streets on your schedule. With professionally produced narration and music accessible on your smartphone, immerse yourself in captivating tales of landmarks like cobblestone streets, Wharf Street, and Henry Wadsworth Longfellow’s home. 

Uncover diverse histories, from lighthouses to prohibition, bootleggers, the underground railroad, Japanese mailboxes, the revolution, and colonial times. 

The tour never expires, providing a comprehensive guide for every visit to this coastal town. With this experience, you’ll always have an immersive adventure waiting for you in Portland.

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5. Stroll Through Commerical Street

Stroll through Commercial Street in Old Port, Portland, Maine, where the salty breeze mingles with the smell of fresh salt air. Cobblestone streets lead you past an array of charming boutiques, art galleries, and 19th-century brick buildings that encapsulate the neighborhood’s cool and quaint atmosphere. 

Explore world-famous restaurants, sip coffee at cozy cafes, and witness the vibrant working harbor. 

In summer, the street buzzes with tourists exploring shops and sailing with the Portland Schooner Co. (more on them later), while fall and winter offer a more intimate experience, drawing locals out to enjoy the serene charm of this waterfront gem.

6. See the first chewing gum factory at the Hub Furniture building

Stroll past the Hub Furniture building while blowing a bubble. While this building is now the home to Hub Furniture, 200 years ago, it was the place where John Bacon Curtis opened up the first-ever chewing gum factory and popularized the treat with the American audience.

➡️Click here to learn about the best walking tours in the Historic Old Port District!

See the Lighthouses

The crown jewel of Portland is its beautiful lighthouses. No trip to this coastal city is complete without visiting at least one if not all five.

Another fantastic thing about visiting the lighthouses? It’s free! Except for paying for parking in a few locations or entering optional museums, the Portland lighthouses are free to visit.

7. Portland Head Light (and Ram Island Ledge Light)

Portland Head Light is Maine’s oldest lighthouse dating back to 1791 and was commissioned by George Washington. Nestled in Fort Williams Park, its iconic tower offers panoramic views of the rugged coastline and the Atlantic. 

The former keeper’s quarters house a historic museum, inviting visitors to delve into centuries of maritime heritage. Whether exploring the 90-acre park or standing at the lighthouse’s base, every angle presents a photographer’s paradise. 

From this lighthouse, you can see nearly all the other lighthouses in the Portland area, including the Ram Island Ledge Light which is situated on an island out at sea and not accessible unless you take a boat or kayaking tour.

8. Two Lights State Park/Cape Elizabeth Lights

Two Lights State Park, home to Maine’s first twin lighthouses commissioned in 1828, offers charming coastal views on its 41-acre grounds. Although the lighthouses are not accessible to the public, visitors can enjoy scenic trails while picnicking and watching sunsets. One of the lights, still operational, adds a magical touch to evenings. 

9. Portland Breakwater Lighthouse (Bug Light Park)

Bug Light, aptly named for its small size, is a charming stop for maritime enthusiasts in Bug Light Park. 

This lighthouse, surrounded by greenery and framing the Atlantic Ocean, provides a unique view of Portland Harbor. Originally constructed in 1855 as a wooden structure, it was later moved and rebuilt in 1875 during the extension of the breakwater. 

Its quaint allure, combined with its proximity to the city, makes Bug Light an easily accessible gem for visitors seeking a delightful and historic maritime experience.

10. Spring Point Ledge Lighthouse

Perched on a stone breakwater extending into Portland Harbor, Spring Point Ledge Lighthouse, completed in 1897, is a captivating structure accessible by a scenic walk. Its unique location against the ocean makes it a photographer’s favorite and the caisson foundation showcases innovative engineering. 

Walking across the breakwater to reach the lighthouse’s base is a quick yet adventurous stroll, providing a memorable experience amid the scenic beauty of Portland Harbor.

➡️ To learn more about the lighthouses of Portland, use my Portland, Maine Lighthouse Guide!

Indulge in Culinary Delights

When thinking about the cities with the best food in the USA, a foodie’s mind usually turns to one of two coastal cities: Portland or San Fransisco. 

While I can’t speak to the delicacies hidden inside of good ol’ San Fran, I can tell you about some of the best places to eat in Portland, Maine.

11. The Holy Donut

In 2010, sensing a gap in Portland’s culinary scene, Leigh Kellis embarked on a doughnut-making journey from her Munjoy Hill kitchen, incorporating a surprising ingredient: potatoes. The unique blend, inspired by a northern Maine recipe, yielded distinctive flavors and textures, leading to the birth of Holy Donut. 

With family support, Kellis opened the first retail location, and the family-owned business has since expanded to four Maine locations. 

Offering around 20 innovative flavors, including seasonal, gluten-free, and vegan options, Holy Donut has become a sought-after doughnut destination, praised for its dense, delicious creations and friendly service. 

Arrive early for the freshest selection, as each location opens between 6 and 7 a.m. But don’t wait too long, the store closes when they sell out.

12. Standard Baking Co.

Discover the essence of European baking at Standard Baking Co., a cherished Portland, Maine bakery founded in 1995 by Alison Pray and Matt James. The journey started with a single French baguette in 1995, and today, with over 15 dedicated staff, the bakery on Commercial Street thrives. 

Committed to quality, Standard Baking Co. meticulously sources organic and local ingredients, ensuring every baked good is crafted with love. Immerse yourself in the tradition of exceptional baking at this beloved local gem.

13. Donut Tasting Walking Tour in Portland’s Old Port

The Sweet Delights Donut Tasting Walking Tour in Portland’s Old Port will have you wandering the streets and indulging your sweet tooth with six unique donut samples from three renowned donut shops. 

This family-friendly adventure offers culinary exploration, historical insight into Maine’s donut creation legend, and exclusive access to The Holy Donut.

14. Green Elephant

An exceptional place for your lunch stop, experience culinary balance at the Green Elephant Vegetarian Bistro. It’s Portland’s haven for mindful dining since 2007. Founded by Chef Dan Sriprasert, the restaurant fuses Thai roots with diverse Asian influences, creating a meat-free menu for all. 

The Green Elephant sources local products, offering an array of Portland beers, home-grown teas, and a superb wine list. Join them for Asian-inspired vegetarian cuisine made with love.

15. Old Port Culinary Walking Tour from Portland

Immerse yourself in Portland’s culinary scene with the Old Port Culinary Walking Tour, a foodie’s delight in the heart of historic Old Port. Led by an expert guide, the tour takes you to five to six carefully chosen eateries, offering diverse tastings of Maine-inspired cuisine. 

Benefit from local insights into Portland’s dynamic food scene, all within an intimate setting for a more personalized experience. Perfect for those seeking traditional Maine delights, this tour unveils the flavors that define Portland’s gastronomic reputation.

16. OTTO Pizza

Since 2009, OTTO Pizza has transformed the ordinary into the extraordinary. From their downtown Portland slice shop, Anthony and Mike have redefined pizza, experimenting with high-quality, local ingredients and creative toppings. 

From the unconventional “Masher” with mashed potato, scallion, and bacon to Thanksgiving dinner-inspired pies, every slice is a testament to their commitment to perfection and elevating the pizza experience. 

The OTTO story, born from two chefs with diverse backgrounds, showcases their passion for crafting serious and unforgettable pizza that transcends tradition, making it a culinary staple in Portland, Maine.

17. Portland’s World of Flavors Tour

Begin a gastronomic expedition with Portland’s World of Flavors Tour, unveiling the diverse tastes that contribute to Portland’s culinary prowess. 

This 2.5-3 hour exploration through historic Old Port and waterfront areas showcases global influences, offering a cosmopolitan culinary journey. 

Experience flavors from Japan, Turkey, Mexico, and India, savoring locally sourced foods with international recipes, customs, and spices. 

Delight in an educational and entertaining experience, unraveling the cultural narratives behind each culinary gem. Designed for adventurous palates, this tour promises an exciting and memorable exploration of Portland’s rich culinary tapestry, making it a must for food enthusiasts visiting the city.

18. The Honey Paw

Awaken your taste buds at The Honey Paw, where the inspiration of a bear indulging in sweet honeycomb translates into a delightful dining experience. 

With steaming broths, savory wontons, and wok-fried noodles, The Honey Paw aims to hit that sweet spot you’ve been craving.

19. Hot Suppa

Discover a delightful culinary journey at Hot Suppa with a diverse breakfast menu catering to all tastes. From the classic Buttermilk Waffle and Grandy Oats Organic Granola to unique specialties like Chicken and Waffle or Shrimp and Andouille Quiche, travelers can expect a satisfying and flavorful experience with each dish. 

The restaurant’s cozy atmosphere and extensive breakfast options make it a perfect stop for visitors seeking a hearty morning meal in Portland.

20. Gross Confection Bar

Gross Confection Bar, a unique establishment in Portland’s Old Port District, is the creative vision of chef Brant Dadaleares. With a diverse culinary background working with renowned chefs, Brant creates component-based desserts and daytime bakery delights. 

The charming setting, housed in an 1883 building, offers a delightful experience where guests can explore the intriguing flavors and textures of Gross’s innovative creations. From breakfast sandwiches to brioche custard buns, the menu is a testament to Brant’s culinary artistry, making Gross a must-visit destination if you’re seeking exceptional desserts in Portland.

Quench Your Thirst at Portland’s Bars, Breweries, and Speakeasies

Portland, Maine is known for its vibrant and diverse craft brewery scene. The city has gained recognition for its numerous breweries, pubs, bars, and speakeasies, all of which offer a wide range of craft beers and unique brews. 

Here are some of the best places to quench your thirst in Portland.

21. Allagash Brewing Company

Allagash stands as a cornerstone of Portland’s vibrant craft beer scene. This place is so influential that its industrial park has become a hub for brewery startups. 

Rob Tod’s Belgian wheat beer, the White, catapulted Allagash to fame, earning it a reputation as a go-to light beer for IPA enthusiasts nationwide. While renowned for the White, Allagash excels in diverse beer offerings, ensuring there’s something to delight every beer aficionado. 

This brewery’s impact extends beyond its signature brew, shaping Portland’s beer landscape and contributing to the success of numerous breweries that emerged from its innovative surroundings.

Its delicious beer has even reached as far as NYC, which is where Mikey and I first discovered it long before we ever visited Portland.

22. Lincoln Speakeasy

Lincoln Speakeasy, concealed below Market Street Eats, provides unbeatable drink deals at a flat $5 rate (hence the name, since it’s Abe Lincoln on the $5 bill). Though cash-only, the warm and friendly atmosphere invites patrons to unwind with budget-friendly cocktails. 

Everyone loves a good speakeasy and navigating the discreet entrance adds to the charm. Only those who are in the know can get in, so it’s a good thing I’ve provided the address below. 😉

23. Eighteen Twenty Wines

Indulge in the unique experience of a rhubarb wine from Eighteen Twenty Wines. Thriving in Maine’s challenging climate, rhubarb, a hardy crop, becomes the star of Eighteen Twenty Wines.

24. Hardshore Distilling Company

Experience the flavors of gin at Hardshore Distilling Company. Here, they enhance the spirits with diverse botanicals, transforming each liquor’s profile into a more complex and enjoyable taste.

25. Maine Mead Works

A few years ago, my husband got really into D&D. Shortly after that, he got really into meads (is there a connection? Yes. Definitely). Well, his getting into meads got me into meads and now the rest is history. 

At Maine Mead Works, you can indulge in honey mead created in various flavors. If you visit, I recommend trying the Lavender Mead.

26. Root Wild, a Kombuchery

Experience an array of kombucha flavors at Root Wild, a kombuchery (as termed by owner Reid). I’m not the biggest fan of kombucha (I’ve tried so hard), but I know lots of people who are and if that includes you, then Root Wild is a must-stop while in Portland. The open and stylish space, featuring details like kombucha-stained wood on the bar, added to the overall appeal.

27. Blyth & Burrows

Nestled on Exchange Street, Blyth & Burrows is a charming cocktail bar spanning two levels in an old brick building. Renowned for signature cocktails and a “small plates” menu, it also conceals a speakeasy in the back. 

Accessible through a secret staircase behind a bookcase, the speakeasy exudes an intimate, vintage ambiance akin to historic hideaways. Named in honor of naval heroes, Commander Blythe and Lieutenant Burrows, the establishment pays tribute to their sacrifice in a mural at the rear, commemorating a naval battle off the coast of Maine during the War of 1812.

28. Pie North

Named after its unique location atop a pizza restaurant, Pie North is a speakeasy with an 80s arcade theme, brimming with nostalgia. Featuring retro-inspired musical decor and classic arcade games, it offers a distinctive and entertaining ambiance, making it a truly one-of-a-kind experience in Portland.

29. Austin Street Brewery

Founded in 2013 by friends Jake Austin and Will Fisher, Austin Street Brewery emerged from their shared passion for craft beer. After years of homebrewing in Westbrook, they self-financed their venture and opened on Industrial Way in Portland in 2014. Maintaining 100% ownership, they prioritize creative freedom and product excellence, utilizing 160 barrels across two facilities.

30. Banded Brewing Co.

Established in 2013 by Ian McConnell, Banded Brewing, originally Banded Horn Brewing, proudly represents Biddeford, Maine’s inaugural brewery. 

The name symbolizes unity, reflecting the brewery’s commitment to collaboration and community. With a focus on balance, Banded Brewing crafts a diverse range of beers, blending traditional and avant-garde styles with a dedication to high quality.

31. Battery Steele Brewing

Battery Steele Brewery originated in a South Portland barn in 2015, with the Flume Double IPA marking its initial pursuit of brewing perfection. Since then, the brewery has garnered loyal customers at its original tap room on Industrial Way in Portland and its kitchen and bar in Wells. 

Meticulously selecting high-quality ingredients, the brewery crafts innovative and world-class craft beers. 

The Wells location, Battery Steele Kitchen+Bar, near the beach, serves elevated pub food paired with exceptional beers. Committed to excellence, Battery Steele collaborates with local farmers and artisans, creating inviting atmospheres for remarkable beer and food experiences.

Enjoy Outdoor Activities

As one of the most beautiful places in the country, Portland, Maine has a vibrant outdoor scene. From scenic trails and waterfront activities to picturesque parks, immerse yourself in the diverse outdoor offerings that make this coastal city an ideal destination for nature enthusiasts.

32. Walk or Bike Peaks Island

Peaks Island is a 720-acre haven for outdoor enthusiasts. And it’s all accessible by walking or biking—that is after you get off the boat and onto its sandy shores.

Peaks Island embodies a lifestyle defined by tranquility rather than any specific attraction. The island is home to around 1,000 year-round residents (swelling to 3,000 in summer), and prioritizes preserving natural beauty and a relaxed atmosphere. 

A mere 15-minute ferry ride from Portland makes it super convenient for anyone wanting to visit for a couple of hours or for a day trip. 

33. Set Sail With Portland Schooner Co.

Set sail on a unique and relaxing voyage through Portland aboard one of the three schooners, all of which are listed on the National Register of Historic Places. 

A sail with Portland Schooner Co. offers a laid-back experience, allowing you to appreciate the beauty of Casco Bay with the invigorating scent of sea air. It’s a perfect exploration mode for those who enjoy maritime charm.

34. Explore Munjoy Hill

Munjoy Hill is a neighborhood in Portland that seeps a lively blend of historical roots and modern charm. Situated on the elevated east end of Portland, it offers a fascinating journey through time. 

Originally settled way back in the 1630s and known for its working-class immigrant community, the area transformed in the 1990s with an infusion of artists and a thriving restaurant scene. 

The influx of artists brought about a dynamic mix of historic charm, trendy boutiques, and acclaimed eateries like Terlingua, all against the backdrop of the city’s finest view at the Portland Observatory (we’ll talk about that more in a bit).

35. Scenic Walk Across the Eastern Promenade

Set on the edge of the ocean, Portland is home to a beautiful waterfront. Walking the 68.2-acre historic public park at the Eastern Promenade is just one of the ways to take in the serene sights. 

From its walking and running trails — both wooded and paved — to dog-friendly areas, boat launches, lively tennis matches, and serene beach days, this well-maintained and easily accessible park offers a splendid playground for a diverse range of visitors, providing a quintessential experience of what makes Portland a truly exceptional city.

This is another fantastic free activity in Portland!

36. Lucky Catch Cruises

This immersive 90-minute maritime tour is not for the faint of heart but it promises a hands-on and educational exploration into one of New England’s vital industries: lobstering. 

Led by a close-knit team of experienced lobstermen, this excursion provides an authentic glimpse into the daily life of lobster harvesting. These seasoned professionals, who operate the tours between their fishing ventures, offer a genuine and up-close experience of where one of the nation’s most treasured foods originates.

Personally, as a vegetarian, I skipped this tour. But for those wanting to know more about where your food comes from, it’s highly rated with many claiming it’s a worthy experience in Portland.

37. Chill at East End Beach

While Maine’s Atlantic beaches are renowned for their cool waters locals swear by the invigorating experience of a dip on a hot day. East End Beach is the sole public beach in Portland (though there are others close by). So, if you’re visiting in the summer, be sure to bring your swimsuit!

➡️ For more tips on what to pack for Portland, Maine in the summer, check out my packing guide here!

This coastal haven draws crowds in the summer for sunbathing, water sports, and serene walks, making it an appealing year-round destination.

38. Casco Bay Islands

While the town of Portland boasts only one public beach a wealth of shorelines awaits on the Casco Bay Islands nearby. 

Comprising six islands that are accessible year-round, each island in Casco Bay has its distinct personality, history, and array of attractions and activities. 

Among them, Cliff Island stands out as the smallest, home to just 60 full-time residents, featuring unpaved roads and a serene, secluded ambiance, making it a tranquil outdoor retreat with limited attractions to draw in crowds.

39. Catch a game at Hadlock Field

If you’re a baseball fan, you’re going to want to catch a swing at Hadlock Field. This is where the Sea Dogs play, a local minor league baseball team that dominates in the summer.

40. Palace Playland

Calling all adrenaline junkies, Palace Playland is one of the best things to do in Portland, Maine!

Okay, so it’s not exactly in Portland. But it’s close enough and worth the drive. Located approximately 20 miles south of Portland in Old Orchard Beach, this 5-acre amusement park stands as New England’s sole beachfront amusement destination.

The park boasts a 24,000-square-foot arcade, offering over 200 classic games like Skee Ball and air hockey. In addition to the extensive game selection, the park offers exhilarating rides like the Sea Viper roller coaster. The amusement park also features a variety of rides suitable for younger visitors, including a carousel and spinning tea cups.

41. Back Cove Trail

Stroll along the 4.2-mile Back Cove Trail loop. In addition to enjoying the peaceful scenery, you can also do a bit of active manifesting by visualizing you own one of the spacious waterfront residences you’re walking by.

42. Stand-Up Paddle Sunset Tour in Portland

Experience the serene beauty of Casco Bay at sunset with the Stand-Up Paddle Sunset Tour in Portland. 

This two-hour excursion is suitable for all skill levels and offers a leisurely paddle along the Eastern Promenade Trail. The tour provides panoramic views of the sun setting over the city as you glide past the undeveloped coastline and seals on the ledges near Mackworth Island. 

Included are a stand-up paddleboard, paddle, and lifejacket, along with a dry bag for your belongings.

43. Sea Kayak to an Island Tour in Casco Bay

Venture on a captivating three-hour Sea Kayak Tour in Casco Bay, starting from Mere Point in Brunswick. Led by a professional guide, you’ll paddle through NW Casco Bay, visiting different islands, and savoring the chance to spot marine birds and seals. 

You can choose a single or two-person kayak and snacks and safety gear are provided. (Always love when a tour provides snacks!)

With group sizes capped at eight participants, you can feel safe on this tour as you receive individual attention from your guide. 

The adventure includes a stop on an island for homemade hot muffins, tea, lemonade, and exploration before returning to the starting point.

Learn Something New at Portland’s Museums

Portland has a rich cultural tapestry that you can explore through its diverse museums. Each gallery offers a unique glimpse into the city’s history, art, and maritime heritage. 

From immersive exhibits to captivating artifacts, explore the vibrant museum scene that reflects the essence of this endearing coastal city.

44. Victoria Mansion

Enthusiasts of architecture and interior design will be captivated by the splendor of the Victoria Mansion, also known as the Morse-Libby House or Morse-Libby Mansion. 

Originally constructed in the mid-1800s as a summer residence for hotelier Ruggles Sylvester Morse, this National Historic Landmark showcases pre-Civil War grandeur. With its exterior modeled after an Italian villa and intricate features such as a square tower, balconies, and piazzas, the mansion is a testament to historical opulence. 

Inside, preserved by the work of renowned designer Gustave Herter, the museum boasts 90% of its original interiors, featuring carved wood panels, gas light fixtures, and ornate decor.

45. Wadsworth-Longfellow House

Constructed post-Revolutionary War, the Wadsworth-Longfellow House served as the residence for four generations of a distinguished family, commemorated today in this museum for their significant contributions to American culture. 

Notably, 19th-century poet Henry Wadsworth Longfellow, a prominent figure in the family, spent his formative years in this historic home. 

Beyond its association with the revered poet, the household has broader historical importance as the oldest standing structure on the Portland peninsula, the inaugural brick dwelling in the region, and Maine’s pioneer home museum.

46. Portland Museum of Art

Portland might not be the biggest city in the States, but it’s got one heck of an art scene. The Portland Museum of Art houses works by renowned figures such as Andy Warhol, Claude Monet, and Winslow Homer. 

The Portland Museum of Art features an extensive collection of American, European, and contemporary art, as well as pieces by Maine artists. 

With over 18,000 items in its collection, including paintings, photographs, sketches, pottery, furniture, silverware, sculptures, and more, you’re going to find something new every time you visit. 

The museum also hosts regular events, including movie screenings, curator talks, and family-focused activities, so make sure to check ahead to see if there’s anything fun scheduled during your trip.

Speaking of which, if you’re super into art, you might want to consider planning your visit to coincide with a First Friday Art Walk. On the first Friday evening of each month, the Arts District buzzes with art enthusiasts exploring local galleries and venues on self-guided tours. Street performers, musicians, and artists of various disciplines showcase their talents in the streets.

47. Children’s Museum and Theatre of Maine

For family-friendly fun in Portland, don’t miss the Children’s Museum and Theatre of Maine. With over 30,000 square feet of space, this museum is one of the best things to do in Portland, offering interactive learning experiences and enjoyment for visitors of all ages.

48. Tate House Museum

Built in 1755 for Captain George Tate, the Tate House served as the residence for this British Royal Navy senior mast agent and his family. 

Responsible for transporting white pines, Maine’s state tree, to England, Tate’s role is explored through hourly site tours showcasing artifacts, furnishings, and the grounds. These elements not only illuminate the 18th-century lifestyle of the Tate family but also emphasize the significance of the mast trade during the era. 

Located approximately 4 miles west of downtown Portland, the Tate House stands as the only pre-Revolutionary home open to the public, offering visitors an educational glimpse into history.

49. Maine Narrow Gauge Railroad Co. And Museum

Located approximately 1.5 miles from the Portland Museum of Art, the Maine Narrow Gauge Railroad Co. and Museum provides insights into train preservation and Maine’s narrow gauge railway history. 

This distinctive two-foot gauge railway system, featuring tracks less than half the width of standard gauges, was a cost-effective solution for traversing Maine’s challenging landscapes of forests, rocky hills, and mountains, connecting rural areas with larger cities from the 1870s to the 1940s.

50. International Cryptozoology Museum

Everybody knows a bigfoot enthusiast. And if no one comes to mind, then odds are you’re probably the cryptid lover in your family. Either way, the International Cryptozoology Museum is a fun way to spend your day in Portland.

Explore the realm of hidden creatures like Bigfoot and Nessie through the study of Cryptozoology, and immerse yourself in the intriguing exhibits at the International Cryptozoology Museum in Portland.

51. Portland Fire Museum

Portland has been totally destroyed by fire a total of four times since its inception. Discover the history of fires in the area by exploring the exhibits at the Portland Fire Museum.

52. Umbrella Cover Museum

Want to visit a museum unlike anything you’ll find in another city? Visit the Umbrella Cover Museum, a gallery that exclusively celebrates umbrella covers.

Experience Portland’s Arts and Culture

Explore Portland’s vibrant arts and culture scene, where the city’s historic and contemporary influences converge. Immerse yourself in world-class museums, eclectic galleries, and dynamic performances, all showcasing the creativity of Portland’s artistic identity.

53. Catch a show at Thompson’s Point

Nestled on the Fore River, Thompson’s Point merges nature and culture with its open-air venue set amid three acres of picturesque lawns. Collaborating with the State Theatre of Portland, the space hosts acclaimed concerts and year-round festivals. 

Summers feature artisanal markets, while winter transforms the site into a family-friendly skating rink. Throughout the seasons, epicurean delights from renowned food trucks add to the allure of this dynamic destination.

54. Explore The Arts District & First Friday Art Walk

The Arts District in Portland offers a rich melting pot of creativity, encompassing diverse expressions from stage performances to museum sculptures. Embracing independent thinking, the district showcases the city’s cultural mindset. 

Don’t miss the First Friday Art Walk, a monthly self-guided tour, for an immersive experience in the vibrant arts scene.

55. Portland Observatory

The Portland Observatory is a historic maritime signal tower dating back to 1807. This famed observatory offers unparalleled harbor views that you won’t find anywhere else in the city.

Here, Captain Lemuel Moody, the observatory’s founder, provided ship alerts for a fee, and with a telescope, he could spot vessels from 30 miles away. Though replaced by radio, the observatory’s charm and history remain, making it a must-visit.

56. Portland Farmers’ Market

Maine has had a longstanding commitment to local agriculture and Portland’s vibrant farmers’ market is a testament to that commitment. Here, over 40 growers, cheesemakers, beekeepers, bakers, and more gather twice a week in summer and fall, and weekly in winter.

57. Coastal Maine Botanical Gardens

Coastal Maine Botanical Gardens is a New England gem that was born from a 16-year dream. The park spans over 300 acres and features themed gardens showcasing the diverse flora of Maine, including dahlias, bees, and rhododendrons. 

While the botanical gardens are not technically located in the city center, it’s not too far of a drive located 60 miles northeast of Portland. This park is worth the visit and stands as the largest botanical garden in the region.

If you’re visiting Portland during the holidays, experience extra magic at the Coastal Maine Botanical Gardens with the dazzling light displays of Gardens Aglow, illuminating the winter darkness on select nights. 

58. Walk through the East Cemetery

Tap into your inner witch and wander through the more historic side of Munjoy Hill by strolling through the East Cemetery, Monjoy’s oldest historical site. If you’re feeling especially gothic, stop by the Dead House, a structure once used to store bodies during winter until the spring thaw. 

This is the perfect free activity in Portland for people who love to add a little bit of macabre into their travels!

See Portland in a New Way with a Unique Tour

Uncover Portland’s rich history and vibrant culture with guided tours offering insights into its culinary delights, historic neighborhoods, and iconic landmarks. I always love a good tour because you can engage in expert-led explorations and gain a deeper understanding of a city’s unique stories and hidden gems.

59. Vintage Fire Truck Sightseeing Tour of Portland, Maine

In this one-of-a-kind tour, you’ll enjoy panoramic views from a red fire engine as you discover picturesque lighthouses, historic landmarks, and vibrant neighborhoods. 

On the Vintage Fire Truck Sightseeing Tour of Portland, Maine, you’ll delight in live narration from your guide, unraveling the maritime past and exploring cobblestone streets. Immerse yourself in the Old Port’s charm, with its boutiques, pubs, and lively dining scene. 

This fun and informative tour offers a great overview of the city’s highlights, providing an unforgettable experience for visitors eager to see Portland’s beauty and history in a distinctive way.

➡️ Plan A Day Trip To Portland, Maine Using This Done-For-You Portland Maine Day Trip Itinerary.

Where to Stay in Portland, Maine in 2024

Portland’s hotel prices can be on the higher side, with a survey by Cheaphotels.com¹ ranking it as the second most expensive city for hotels in the United States. 

While I was visiting Portland with my family, we went on a tour of the Customs House and were jokingly informed that the hotels in the area were so pricey that one could potentially charge $250 a night to rent out the 12-square-foot bank safe hidden in the building.

Given the expense of Portland hotels, a great alternative is to consider staying in an Airbnb or VRBO.

The Cozy BnB

Nestled in the charming town of Scarborough, we found a delightful Airbnb hosted by Steven. The Rustic Suite near downtown Portland and Beaches lived up to its listing, offering a cozy, clean, and comfortable retreat.

The space is a studio apartment with a master bed in the front, an additional room in the back creating a family room/TV space, and a super fun loft area with two twin beds overlooking the family room. This unique setup provided more comfort than a traditional hotel and allowed us to explore the historic neighborhood surrounding one of the U.S.’s oldest towns.

Conveniently located just a 10-minute drive from downtown, this pet-friendly accommodation was a perfect choice.

Hotels

If vacation rentals aren’t your preference or you wish to stay closer to downtown, here are some highly recommended hotels in Portland, Maine:

📍 Luxury: The Press Hotel

For a blend of history and luxury, indulge in a stay at the Press Hotel. 

Occupying a century-old building that was once home to the Portland Press Herald newspaper, this pet-friendly 4-star hotel in the heart of downtown offers refined details, distinctive features, and a rotating art gallery. 

While it may be on the pricier side, a night at the Press Hotel ensures an unforgettable experience in Portland.

📍 Mid-range: The West End Inn

Opt for the charming West End Inn for a mid-range lodging experience. Situated in downtown Portland, this inn provides convenient access to key attractions, including the Victorian Mansion, just a half-mile away. Enhance your stay with a delightful breakfast menu and themed dinner nights.

📍 Budget: Holiday Inn Portland-by the Bay

For a more budget-friendly option without sacrificing impressive views and valuable amenities like parking and e-bikes, consider the Holiday Inn Portland-by the Bay. Who needs luxury living when you have an entire city to explore?

📍 Hostel: Black Elephant Hostel

If you’re seeking budget accommodations with a touch of vibrancy, the Black Elephant Hostel is your ideal choice. 

This colorful and fun hostel, the first and only one in Portland, was created with the mission of uniting people and cultures, bringing hostel culture to this historic New England town.

➡️ For a complete guide on where to stay in Portland, check out my blog reviewing the 15 Best Unique & Historic Hotels in Portland, Maine here.

Getting around Portland, Maine

Navigating the downtown area of Portland is a delightful stroll, and once you’ve parked your car, you might find you won’t need it until you’re ready to bid adieu to the Old Port area.

However, if your adventures lead you to explore lighthouses or other attractions beyond the city center, you’ll want reliable wheels. Here are transportation options to consider during your stay in Portland.

Biking

While the city center offers a charming walkable experience, reaching attractions like lighthouses may call for alternative transportation. 

Portland provides an adventure-filled option with numerous well-marked bike lanes in and around the city. Many hotels offer bike rentals for day use, and public bikes are available, allowing you to pedal your way around and explore the sights. 

Keep in mind that biking is a leisurely mode of transportation, so plan your itinerary accordingly to ensure ample time at each destination.

Public Transportation

For a convenient city-wide experience, Portland boasts a reliable bus service, known as METRO. The easiest way to pay for rides is with cash. It’s advisable to have some loose change on hand, as each journey typically ranges from $1 to $4 and you’ll need exact change. 

Some locals have been navigating Portland without a car for years, relying solely on the efficient bus system.

Ride-Share

Opting for popular ride-sharing services like Uber or Lyft is a pricier yet quicker and more convenient alternative, especially when time is of the essence during your day in town. This option is less expensive than renting a car. It’s also a responsible decision if you plan on indulging in local brews and need a safe ride back to your accommodation.

Car

For the utmost flexibility, exploring Portland by car is the easiest way to get around. Navigating the city is straightforward, and though parking may be a bit pricey, there are plenty of options, including paid lots, on-street parking, and garages. 

Metered parking is a cost-effective choice at $2.50 per hour. Keep in mind that on-street parking in Portland is complimentary from 6 p.m. until 9 a.m., Monday through Saturday, as well as all day on Sundays and major holidays. To streamline your parking experience, consider using the PassportParking App.

Whether you’re pedaling, hopping on a bus, summoning a ride-share, or navigating the city on four wheels, Portland ensures you have convenient options to make the most of your visit.

What to Pack for Your Trip to Portland, Maine in 2024

When exploring the coastal regions of Maine, like Portland, be prepared for cooler temperatures, even in summer. Ensure you pack suitable cold-weather attire such as pants, sweaters, long shirts, and waterproof shoes.

10 Essential Packing Items You’ll Need for Portland, Maine

Use this packing list to make sure you remember to bring everything you need on your trip to Portland, Maine.

Clothing and footwear

You may already have an idea of what to pack for Portland, Maine. But make sure you also include these three essentials.

Hiking Boots

Breathable Water Shoes

Stylish Dress

Toiletries

While you probably know your basic toiletries by heart, don’t get on that plane to Portland without double checking you have these items.

Solid Shampoo Bar

Insect Repellent

Hand Sanitizer

Toiletry Bag

Travel Essentials

These travel essentials are going to make your trip to Portland so much easier.

Portable Windproof Umbrella

Travel Packing Organizers

Compact Portable Charger

Travel Insurance

Ensure peace of mind on every trip with World Nomads Travel Insurance, offering affordable and comprehensive plans for all.

Evaluate insurance plans on World Nomads Travel Insurance →

➡️ For a more detailed Portland packing list, check out my complete Portland packing guide for any season here.

FAQs About Visiting Portland, Maine

You’re almost ready to set sail to one of the United States’ most charming coastal towns. Before you start your trek, let’s go over some frequently asked questions about visiting Portland, Maine.

Is Portland, Maine Worth Visiting?

Portland, Maine is absolutely worth visiting! Portland is a picturesque coastal city with a rich history, vibrant culture, and diverse attractions, making it well worth a visit.

Is Portland, Maine, Worth a Day Trip?

Yes, Portland is compact and offers a lot to explore, making it perfect for a rewarding day trip filled with unique experiences.

How Much Time Do You Need in Portland, Maine?

While a day trip can cover key attractions, spending 2-3 days allows for a more leisurely exploration, enjoying the city’s diverse offerings.

When is the Best Time to Visit Portland, Maine?

The best time to visit is during the summer and early fall when the weather is pleasant, and outdoor activities are abundant. Fall foliage adds extra charm.

Can You Do a Day Trip to Acadia National Park from Portland, Maine?

While Acadia National Park is approximately 3 hours away, a day trip is possible but may be rushed. Consider an overnight stay for a more relaxed visit.

What to Do in Portland, Maine, When it Rains?

Explore indoor attractions like museums, art galleries, and cozy cafes. Attend a live performance or indulge in the city’s vibrant culinary scene.

How to Explore Nearby Towns and Attractions?

Options include renting a car, taking public transportation, or joining guided tours. Consider day trips to coastal towns, lighthouses, and nature reserves.

Final Thoughts on what to do in Portland, Maine

So there you have it, folks! From exploring historic neighborhoods to savoring local cuisine, there are so many more things to do in Portland, Maine than people realize. 

As you plan your visit to Portland, I hope this guide sparks excitement and anticipation for the adventures that await. If you’re eager to make the most of your trip, don’t forget to check out my detailed guide, Perfect Day Trip to Portland, Maine: The Best 1-Day Itinerary. It’s packed with insights, recommendations, and hidden gems to elevate your experience. 

So pack your bags and embrace the small-town feel of the coastal city. With so much to do, you’ll likely find yourself visiting Portland over and over again. 

Additional Resources:

Taking a quick day or weekend trip over to Portland? Check out my recommended itinerary for what to do in Portland for a day.

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