The Open Road Travel

Portland is one of New England’s biggest, busiest, and best cities, yet one that is still often overlooked in favour of locations like Boston and Providence. In our guide to the 15 best things to do in Portland, Maine, we hope to change all that.

We are going to show you the very best activities the city has to offer and cover options for a wide range of different tastes and interests. This should ensure everyone can plan a perfect travel itinerary for their dream vacation to “The Forest City”.

So, if you plan to visit Portland for yourself and want to make sure you don’t miss any of the highlights, this is the article for you.

Portland is Maine’s most populous city, with just under 70,000 residents. Being established in 1786 makes it the 7th oldest permanent settlement in Maine, while it was also the first place in the state to be incorporated as a city, which happened in 1833.

The name Portland comes from the Old English word “portlanda”, which means “land surrounding a harbour”. This comes from the fact that it has the largest seaport in the New England region, making it an extremely important location.

This includes its Old Port district, which is well known for its vibrant nightlife and historic buildings. The Arts District also features one of the largest collections of museums, galleries, studios, and various other artistic establishments in Portland.

The best time to visit Portland for most will be in July and August. This is when the city experiences its warmest, driest period, so is perfect to ensure you can explore in peace, without worrying about your trip being derailed by the weather.

However, late September to the end of October is a great time to visit for those who want to see the iconic New England fall foliage, as this period is when the colour of the leaves is at its most vibrant.

As we move to our list of the 15 best things to do in Portland, Maine, I am going to suggest a broad range of options. These will include things to appeal to travellers of all different interests, while ensuring you have something to cover everything that Portland is known for.

The Victoria Mansion is a 19th century villa style home that boasts a stunning Italianate brownstone exterior and lavishly decorated interiors. Built for hotelier Ruggles Morse and later sold to local merchant Ralph Libby, it is also known as both the Morse-Libby House and Morse-Libby Mansion.

Incredibly well preserved, its unique features include a Turkish smoking room, verandas, and stained glass windows. It also houses a collection of artefacts owned by its famous families, including art, furniture, glassware, paintings, porcelain, and silverware.

Now a museum, visitors can explore the historic interiors and appreciate the architecture of this building that has been listed on the U.S National Register Of Historic Places since 1970.

109 Danforth Street, Portland, Maine, 04101, United States

Established in 1882 in The Arts District of Portland, the Portland Museum Of Art is Maine’s oldest art institute, and its collection of over 22,000 pieces makes it the largest too. Its 3 buildings are designed to represent the American art, culture, and style of the centuries the museum has existed for.

Displaying paintings and sculptures by some of the world’s most famous artists, covering styles such as European Impressionism and Surrealism, it attracts more than 140,000 visitors each year and is a must visit attraction for any art fans who visit Portland.

7 Congress Square, Portland, Maine, 04101, United States

Fort Allen Park is a beautiful, 9 acre grassy park on the site of the 18th century Fort Allen. It is full of historic artefacts and monuments, including weapons and parts from early 20th century U.S. battleships, Civil War weapons and memorials, and a 19th century band stand.

When combined with a beautiful gazebo, tranquil seating areas, and stunning coastal views, Fort Allen Park is a great place to combine education and relaxation.

49 Eastern Promenade, Portland, Maine, 04101, United States

The Maine Narrow Gauge Railroad is a 1.5 mile (2.4 km) stretch of narrow gauge railroad laid in 1993 that is identical to the historic railways of the region. It runs parallel to both the Eastern Promenade and Casco Bay coastline.

Visitors have a choice of 7 historic diesel and steam locomotives from the early to mid-1900s to hop on board and enjoy stunning views from while being regaled with historical facts about the region. This makes it a fabulous way to relax, learn, and take in the landscape all at the same time.

49 Thames Street, Portland, Maine, 04101, United States

The Maine Historical Society is responsible for collecting, preserving, and displaying artefacts dedicated to the state of Maine. It operates a museum and library out of the Wadsworth-Longfellow House which, having been built in 1785, is the oldest building on the Portland peninsula.

Named after legendary American poet and former resident Henry Wadsworth Longfellow, the house was listed on the U.S National Register Of Historic Places in 1966. Visitors can study its architecture, explore its gardens, and examine its many artefacts to learn all there is to know about Maine.

489 Congress Street, Portland, Maine, 04101, United States

Congress Street is Portland’s main street, and it runs through the heart of the city. Filled with historic buildings and attractions, fabulous bars, shops, and restaurants, and various other unique and entertaining sights, it is a great place to take a stroll and see what the city of Portland is all about.

Congress Street, Portland, Maine, 04101, United States

In 2008, the 1970 Children’s Museum Of Maine and 1923 Children’s Theatre Of Maine merged into a single, all-encompassing complex. Known for its extensive range of permanent and rotating large scale, interactive exhibits, it covers topics like camera obscura, science, industry, art, and acting.

Anyone who decides to visit Portland with kids should definitely drop in to give the younger members of their party an entertaining and educational treat they won’t forget in a hurry.

250 Thompson’s Point Road, Portland, Maine, 04102, United States

The Portland Observatory is a 86 foot (26 metre) tall maritime signal tower erected in 1807. Said to be the only one left of its kind in the United States, it has been listed on the U.S National Register Of Historic Places since 1973.

Now a functioning museum, visitors can study its various exhibits to learn about the history of both the tower and the Portland maritime service. When they are finished, they can then head to the observation deck to take in some truly stunning views of the coast and city.

138 Congress Street, Portland, Maine, 04101, United States

The Cushings Island Ferry runs tours from the Old Port, across Casco Bay, to Cushings Island.

Take a relaxing voyage through the waters, seeing the various islands off the coast of Portland, before being delivered to an island boasting beaches, watchtowers, and a fortress, where you can explore to your heart’s content and enjoy a truly unique day when you visit Portland.

144 Commercial Street, Portland, Maine, 04101, United States

Fort Gorges is a 19th century island military fort located just off the coast of Portland. While it never had troops stationed here, it was used for storing military supplies during a number of conflicts. It was then listed on the U.S National register Of Historic Places in 1973.

Now converted into a park, explorers can take private boats and tours to the island, where they are free to explore its various buildings and structures, while enjoying the views from the island.

Hog Island Ledge, Portland, Maine, 04106, United States

Named after Abraham Lincoln, Lincoln Park was created in the immediate aftermath of the city’s 1866 Great Fire. It was then listed on the U.S National Register Of Historic Places in 1989.

Covering 1.8 acres, it is known for its iconic fountain and areas of wide open green spaces surrounded by trees. Boasting a fabulous network of walkways and countless benches to rest on, it is a great place to relax and enjoy the more natural side of Portland for a while.

Congress Street & Pearl Street, Portland, Maine, 04101, United States

Western Promenade is an 18.1 acre historic district and park that was established in 1836 and has been listed on the U.S National Register Of Historic Places since 1989. Set on bluffs on the Portland peninsula’s west side, it is full of scenic trails that weave through historic statues and buildings.

It is a truly fabulous destination for those who want to spend a day exploring and appreciating the history, architecture, and landscape of Portland at their own pace.

Valley Street, Portland, Maine, 04102, United States

The International Cryptozoology Museum is a unique establishment dedicated to mythical creatures like Bigfoot, the Loch Ness Monster, mermaids, and more.

Featuring various accounts, artefacts, photos, and more, it is a great stop for those with open minds to explore how these legends were established and whether or not they could possibly be true.

32 Resurgam Place, Portland, Maine, 04102, United States

Movie buffs will definitely want to take a trip to the John Ford Statue when they visit Portland. An attraction dedicated to the legendary movie director who holds the record for most best director Academy Awards with 4, this massive statue depicts him sitting in his director’s chair.

With John Ford having been born and raised just outside of Portland, it honours one of the area’s most successful people and is a fabulous place to snap a photo.

4 Pleasant Street, Portland, Maine, 04101, United States

East End Beach is a beautiful, sandy beach backdropped by greenery and walking trails. Featuring boat launches, a small range of facilities, and stunning coastal views, it is the best place in Portland for those who want to spend a day lazing on the sand or having fun in the water.

Eastern Promenade Trail, Portland, Maine, 04101, United States

The Portland Harbor Hotel is a beautiful, 4-star hotel in the historic Old Port area that is perfectly situated to offer both stunning views and easy access to the city’s top attractions.

Each of its spacious, luxury rooms is well equipped with things like a flat screen TV, refrigerator, and air conditioning, while many will also include a sofa and spa bath, as well as stunning views.

The communal areas then boast an equally liberal supply of amenities, including a bar, restaurant, meeting facilities, and luggage storage. Free Wi-Fi is also available to every guest in all public areas of this pet friendly hotel, while private and valet parking are both available for an additional fee.

As we conclude our guide to the 15 best things to do in Portland, Maine, you should now have everything you need to plan a perfect travel itinerary for a trip to “The Forest City”.

From all the best attractions to key information like the best time to go and best place to stay, you have all the ingredients for a dream vacation. All you have left to do now then is start getting things booked, so you can begin looking forward to when you visit Portland for yourself.