When it comes to exploring Portland, Maine, remember that there’s no one-size-fits-all itinerary for this vibrant city. Portland, the largest city in the Pine Tree State, boasts a rich maritime history, scenic waterfront trails, and a plethora of artisanal shops, top-notch restaurants, and craft breweries.
As a lifelong Mainer and former resident of Portland, I have a few tips to enhance your trip planning. Firstly, make sure to pack comfortable shoes and layers, as even the warmest summer days can turn chilly at night.
Portland can be divided into two main areas: the on-peninsula region (where most recommended activities are concentrated) and the off-peninsula area (encompassing the outskirts and various residential neighborhoods). While walking, biking, taxis, and public transportation are convenient options for exploring the peninsula, having a car may be necessary if you plan to venture beyond. Keep in mind that parking can be challenging, especially during peak travel seasons, so consider opting for hotel parking, with The Francis offering complimentary parking to guests.
From historical trails to island excursions, here are 18 fantastic things to do in Portland, Maine:
1. Stroll along the Eastern Promenade.
For a picturesque harborside walk, head to the Eastern Promenade, a two-mile trail starting downtown and connecting to Fort Allen Park and East End Beach. Along the way, you can spot nearly 200 bird species, sample treats from food trucks at Cutter Street parking lot, and enjoy the scenic views of Casco Bay from East End Beach. Don’t miss the opportunity to rent a kayak for a unique perspective of the city or let the kids play at the playgrounds.
2. Experience the Portland Observatory.
For a panoramic view of the city, visit the 86-foot-tall Portland Observatory. Climb the seven flights of stairs at your own pace or join a guided tour to delve deeper into the building’s history. This historic tower, the last remaining maritime signal station in the U.S., is operated by Greater Portland Landmarks and offers seasonal openings. The organization also conducts walking tours of various Portland neighborhoods.
3. Indulge in drinks at Luna Rooftop Bar.
Located on the Portland waterfront, Luna Rooftop Bar at the Press Hotel offers a prime location to enjoy artisanal cocktails and small bites while soaking in panoramic waterfront views from the sixth floor. If you’re a guest at the hotel, don’t miss the delightful pastries and specialty lattes at Inkwell, situated on the street level.
4. Explore the art gallery at The Press Hotel.
The Press Hotel, housed in the former headquarters of the Portland Press Herald, features an impressive art gallery showcasing works by Maine’s emerging and established artists. Even if you’re not staying at the hotel, a visit to the public lower-level gallery is worthwhile. Afterward, enjoy a beverage at the lobby bar, which pays tribute to the journalism industry with a display of 62 vintage typewriters.
5. Attend events at Thompson’s Point.
Thompson’s Point is a hub for entertainment, housing a children’s museum, hosting year-round special events, and featuring amenities like a skating rink in winter. During the summer, enjoy free and ticketed concerts in collaboration with the State Theatre, along with a variety of food trucks and beverage options. On select Sundays, explore the Maker’s Market at the restored railroad shed, offering a chance to shop for local artisans’ creations while sipping on mimosas.
6. Embark on a brewery tour.
With Portland’s thriving craft beer scene, it’s impossible to visit just one brewery. Join guided walking or bus tours of the city’s pubs and breweries through Maine Brew Bus. Alternatively, create your personalized brewery itinerary using the Maine Beer Trail planner to explore Portland’s renowned breweries at your own pace.
7. Delight in tacos at Bird & Co.
While Portland is famous for its fresh seafood, Bird & Co. offers a delectable selection of 12 taco varieties that cater to diverse palates. Whether you prefer vegan, vegetarian, or meat options, the creative menu is sure to impress. Be sure to sample a variety of tacos to fully experience the culinary delights this eatery has to offer.
8. Appreciate art at the Portland Museum of Art.
Whether you’re an art enthusiast or seeking indoor activities on a rainy day, a visit to the Portland Museum of Art is a must. Established in 1882, this institution showcases temporary exhibits and a vast permanent collection featuring over 19,000 works, including pieces by renowned artists like Andy Warhol and Claude Monet. Located in the vibrant Arts District, the museum spans three architecturally striking buildings and includes a beautiful sculpture garden. Check the calendar for special exhibitions or plan your visit around free admission times, such as Friday evenings and every third Thursday of the month.
9. Take a ferry to Peaks Island.
Escape to the water by taking a short, affordable ferry ride to Peaks Island, offering a serene retreat just minutes from Portland. Enjoy the ocean breeze, relax at a quiet picnic spot, savor treats from local establishments like Down Front Ice Cream or Peaks Cafe, and explore unique shops. Opt for kayak and bicycle rentals or cruise around the island in a golf cart for a leisurely day trip. For an extended stay, consider booking accommodations at [ppp19].
10. Shop at The Black Box.
Located on Washington Avenue, The Black Box is a collection of repurposed shipping containers housing various small businesses. Explore establishments like Moonday Coffee, Thicket Jewelry, Pinebury, and Bay Bowls for a unique shopping experience. As an incubator space, the lineup of businesses may vary, so check the website for the latest offerings.
11. Ride the Maine Narrow Gauge Railroad.
Hop aboard the Maine Narrow Gauge Railroad for a scenic 40-minute train ride along the Eastern Promenade, offering stunning views of Casco Bay. Before or after the ride, take time to explore the museum’s exhibits. During the summer, don’t miss the Ice Cream Train experience, where each passenger receives a cone, or enjoy family-friendly rides on the festive Polar Express during the winter season.
12. Discover hidden treasures on Stevens Avenue.
A hidden gem in the Deering Center neighborhood, Stevens Avenue offers a unique shopping and dining experience. Start your day with a cup of coffee at Tandem Coffee Roasters, where 50% of profits support farmers. Explore The Honey Exchange for beekeeping insights and a selection of local goods, or visit Ferdinand for curated home goods, natural beauty products, and local beverages. For distinctive souvenirs, check out More & Co., a boutique offering carefully selected items labeled as “desirable nonessentials.”
13. Indulge in fresh seafood at Luke’s Lobster.
Experience the charm of dining by the working waterfront at Luke’s Lobster, where you can enjoy fresh seafood sourced directly from local fishermen. With locations worldwide and a commitment to sustainability as a Certified B Corporation, Luke’s Lobster offers a unique dining experience that connects diners to the local fishing community.
14. Enjoy live music.
Portland boasts a vibrant music scene, with venues like Port City Music Hall, State Theatre, Aura, and Thompson’s Point hosting a diverse range of musical performances. Whether you’re into rock, jazz, or indie music, you’ll find a venue to suit your musical preferences and enjoy live entertainment in the city.
15. Go Lobstering with Lucky Catch Cruises.
Experience the traditional lobster fishing industry firsthand with Lucky Catch Cruises, offering interactive tours focused on Maine’s iconic seafood export. Join a 90-minute excursion around Casco Bay to learn about lobstering, try your hand at hauling traps, and admire scenic views of the coast, forts, and lighthouses. After the cruise, purchase lobster at wholesale prices and have it prepared at the neighboring restaurant, DiMillo’s on the Water.
16. Wander the historic Old Port streets.
Explore the cobblestone streets of the Old Port, a charming district in downtown Portland characterized by 19th-century red brick buildings, trendy boutiques, lively bars, and entertainment venues. Despite the summer crowds, the Old Port retains its quaint atmosphere, making it an ideal location for a leisurely stroll. Pair your visit with a Windjammer cruise offered by Portland Schooner Co. for a memorable experience on the bay.
17. Visit Maine’s oldest bookstore.
Founded in 1886, Sherman’s Books & Stationery has been a beloved destination for book lovers in Maine. Browse a selection of books by local authors, bestsellers, gifts, toys, and specialty Maine-made products at the Exchange Street location in Portland. Sherman’s Books & Stationery also offers a unique shopping experience, making it a must-visit for book enthusiasts and gift seekers.
18. Dine at The Porthole.
While The Porthole may be bustling with activity, this waterfront eatery is a must-visit spot in Portland. Established in 1929 to cater to fishermen before their daily expeditions, The Porthole offers a memorable dining experience. Indulge in dishes like lobster Benedict for breakfast or baked stuffed haddock for dinner, and savor the fresh flavors of Maine seafood in a historic setting.
Enjoy your exploration of Portland, Maine, and make the most of these diverse and exciting activities to create lasting memories in this charming coastal city.