Explore the lively Portland harbor, take a tour of the lighthouses, visit the museums, dine at great restaurants, and have fun on the water. Whether you are planning a romantic trip, weekend getaway, day trip, or a family vacation, Portland, Maine, is a fun destination. My personal favorites? I love Portland's location on the ocean, its maritime charm that's reflected in everything from art to cuisine.
Portland, ME Highlights:
- For Foodies: Explore the Old Port District
- For Lighthouse Lovers: Visit Portland Head Light
- For Art Enthusiasts: Tour the Portland Museum of Art
- For Adventurers: Take a ferry to the Casco Bay Islands
- For Beer Lovers: Visit award-winning breweries
Best Time to Visit Portland, ME
The best time to visit Portland is from May to October, when the weather is mild and ferries are running. I also enjoyed outdoor dining in the summer.
How to Get to Portland, ME
- By Plane: Fly into Portland International Jetport (PWM), just 10 minutes from downtown.
- By Train: Amtrak’s Downeaster connects Portland to Boston and other New England destinations.
- By Car: Portland is located along I-95, about 2 hours from Boston and 5.5 hours from New York City.
Where to Stay in Portland, ME
- The Press Hotel – Chic boutique stay
- Portland Harbor Hotel – Elegant hotel with nautical décor
- Black Elephant Hostel – Budget-friendly
Best Things to Do in Portland, ME
1. Shop, Dine, and Soak Up Waterfront Views Along Commercial Street
Rating: ★★★★★
Commercial Street runs along the edge of the city's downtown district along the water and is home to an array of busy restaurants, cafés, bars and boutiques. Resting right on the water’s edge, Commercial Street is a welcome haven for tourists and locals alike, with fresh sea breezes, beautiful maritime scenes of ships coming and going, and fisherman hauling in the catch. Cobblestone streets lined with quaint, charming buildings from the late 19th and 20th centuries give the area an old-world European look. Shops selling succulent seafood and other Maine treats offer a quintessential New England feel. If you are wondering what to see in Portland, Commercial Street is a great place to visit. Architectural gems will take you back in time, such as the Customs House, a unique fusion of Renaissance Revival and Second Empire architectural styles.
2. Climb to Panoramic Harbor Views at the Portland Observatory
Standing as a beloved symbol of Portland’s rich maritime heritage with spectacular views over the harbor, the Portland Observatory is a historic tower located on Munjoy Hill. Built in 1807, the tower is one of its kind, providing communication between ships and the shore using signal flags and a telescope. The telescope was situated in the observatory's cupola (lantern) and could identify ships miles out to sea. Unfortunately, the telescope disappeared from the tower in 1939. Designated as a National Historic Landmark in 2006, the 86-foot (26 m) tall observatory tower is now a museum that is open to the public to explore. Visitors can enjoy guided tours of the tower which focus on the importance of the structure to maritime history and the changes in the seafaring port of Portland in the last two hundred years. If you are looking for best things to do in Portland with the family, this is a great stop.
138 Congress St, Portland, ME 04101, Phone: 207-774-5561, Map
3. Explore Masterpieces and Modern Works at the Portland Museum of Art
Founded as the Portland Society of Art in 1882, the Portland Museum of Art is the oldest and largest public art institution in the state of Maine. Located in the downtown district of the city known as The Arts District, the museum houses a collection of over 17,000 decorative and fine arts objects dating from the 18th century to the present. These works are separated into different genres, such as the State of Maine Collection, the European Collection, the American-art based Elizabeth B. Noyce Collection, with works by Homer, Rodin, Degas, Bellows and Wyeth. The Museum boasts three architecturally significant buildings that unite three centuries of American art and culture, with the Charles Shipman Payson Building standing as the face of the museum since it opened in 1983. If you are looking for great things to do in Maine, this unique museum is a must-see. The museum also hosts a number of educational programs and events throughout the year, such as gallery talks, PMA movies, and special exhibitions.
Portland Museum of Art, Seven Congress Square, Portland, Maine 04101, Phone: 207-775-6148, Map
4. Take a Guided Walking Tour and Taste Local Flavors with Maine Day Ventures
Explore Portland’s culinary scene with a fantastic foodie tour. Maine Foodie Tours offers a variety of tours based on the delicious fare produced from the abundance of dairy products, fresh fish, seafood, and organic fruit and vegetables farmed in the region. Maine’s chefs, artisans, brew masters, and bakers come together to create imaginative and flavorful local dishes – all of which can be tasted and enjoyed on one of the tours. These award-winning tours are led by local aficionados that are passionate about food and their city, and will share their knowledge with you visiting various neighborhoods in the city including the Old Port. Maine Foodie Tours also offers cooking classes for all levels of the chef, from beginner to advanced, as well as private tours for special occasions and events.
What to do if you are traveling with kids:
5. Step Into Civil War and Island History at the 5th Maine Museum
Located near Portland on Peak Island, the 5th Maine Museum is a small museum just a 20-minute ferry ride from the city, with boats leaving nearly every hour. The museum is then around a 10-minute walk from the landing, but golf cart rentals and the island taxi are available from the boat landing as well. The 5th Maine Museum’s first floor is devoted entirely to the history of the Fifth Maine regiment, with pictures and artifacts lining the museum walls. The second floor, however, is focused on the history of Peak Island dating back to the 1800’s through present day.
5th Maine Museum, 45 Seashore Ave, Peaks Island, ME 04108, 207-766-3330, Map
6. Marvel at Gilded Age Splendor in the Victoria Mansion
Also known as the Morse-Libby House, Victoria Mansion is one of America’s best examples of pre-Civil War opulence and glamour. Built between 1858 and 1860 as an exquisite summer home for Ruggles Sylvester Morse, a Maine-born proprietor of luxury hotels who made his vast fortune in New Orleans, Victoria Mansion was constructed in the Italian villa style that was fashionable in the mid-nineteenth century. The Mansion’s beautifully preserved interiors were designed by Gustave Herter and still boast over 90% of the furnishings he designed for the original owner. Guided tours are offered May through October, as well as tailor-made group tours for particular interests. The mansion is a unique historic attraction in Portland that offers an active roster of educational programs for both students and adults interested in studying life as it was during the nineteenth century.
Victoria Mansion, 109 Danforth St, Portland, Maine 04101, Phone: 207-772-4841
7. Savor Creative Small Plates and Bold Flavors at Central Provisions
Central Provisions in Portland’s Old Port has been one of the city’s hotspots for years, with tightly packed tables, a buzzing subterranean bar and a seasonal menu that specializes in small plates. Broken into categories of raw, cold, hot, and hearty, dishes are ordered a few at a time and arrive at the table as they are prepared - simple, easy eating in a comfortable and welcoming environment. Desserts are the same with sweet treats including local strawberry shortcake, and salted caramel mousse with cocoa and coffee. Friendly, efficient staff collaborates with diners to interpret the menu and offer advice on both the dishes and wines to accompany them. Due to its extreme popularity, the restaurant does not take reservations, so order a drink at the elegant bar while you wait for a table.
Central Provisions, 414 Fore Street, Portland, Maine 04101, Phone: 207-805-1085
Activities and Attractions for Couples and Singles:
8. If You Love Live Music, Enjoy a Performance by the Portland Symphony Orchestra
Established in 1923 and recognized as one of the top orchestras of its size in the country, the Portland Symphony Orchestra is a fully professional symphony orchestra that performs a wide variety of concerts at the Merrill Auditorium throughout the year. Directed by Robert Moody, the orchestra frequently features renowned guest artists and hosts the “Magic of Christmas” which has been a much-loved tradition for over 25 years. The Portland Symphony Orchestra (PSO) offers a range of educational programs and workshops for students to engage with symphonic music and explore the beauty of classical music. The PSO also contributes to the local community through events such as “Make Music Lovers” Luncheons, where guests can enjoy an in-depth look at musical topics from the PSO concert season and converse with Robert Moody and other special guests. If you are looking for romantic things to do in Portland at night, watch a performance by the Portland Symphony Orchestra.
Portland Symphony Orchestra, 85 Exchange Street 4th Floor, Portland, ME 04101, Phone: 207-773-6128, Map
9. Explore Myths, Legends, and Mysterious Creatures at the Cryptozoology Museum
The world’s only cryptozoology museum, the International Cryptozoology Museum celebrates “cryptozoology” which is the quest to discover hidden creatures, from elusive cougars to the famously mysterious Bigfoot. Exhibits at this fascinating museum include an 8-foot tall Bigfoot made of musk ox hair, the Jersey Devil, the Mothman, various lake monsters, and the Abominable Yeti. The museum is also home to displays of unusual animals known as “cryptids” that were only recently recognized as being “real” such as the Komodo dragon, the panda, and the coelacanth. Inspiring curiosity for visitors of all ages, the museum is kocated in downtown Portland and is open every day, except Tuesdays.
International Cryptozoology Museum, 32 Resurgam Pl, Portland, ME 04102, Phone: , Map
10. Sip Craft Brews and Tour a Maine Beer Icon at Allagash Brewery
An independent craft brewery in Portland, Maine, Allagash Brewery was founded by Rob Tod, a 2019 James Beard Award winner for “Outstanding Wine, Spirits, or Beer Professional.” Known for its Belgian-style Allagash White wheat beer, this Certified B Corp brewery also produces spontaneously fermented beers, barrel-aged beers, sours, and more. Allagash Brewing has been consistently recognized as one of the best places to work in Maine for many years and loves to give back to the local community that has supported the brewery since 1995. The brewery is also recognized as one of the country’s fifty largest craft breweries.
Allagash Brewery, 50 Industrial Way, Portland, ME 04103, 207-878-5385
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