Amazing Things To See & Do In Portland, Maine

photo courtesy Portland Museum of Art
photo courtesy Portland Museum of Art
Alana Jajko

The largest city in the U.S. state of Maine, Portland has much to offer, with its most visited areas being the historic Old Port and the Arts District. In addition to these popular locations, the Portland area has much to offer with historical landmarks and museums, shopping, award-winning restaurants, and activities in areas just outside the city as well. We have compiled a list of some of the best things to do and see in the coastal city of Portland, Maine.

Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.

Portland Museum of Art

Located at the heart of the downtown arts district in Portland, Maine, the Portland Museum of Art features a collection of more than 18,000 objects with decorative and fine arts dating from the 18th century to the present. PMA displays works of Maine-natives, highlighting the rich artistic tradition of the state and its artists, as well as the largest European art collection in Maine, and a diverse range of contemporary work. Some of the Maine artists featured include captivating works by Winslow Homer, Marsden Hartley, Rockwell Kent, Louise Nevelson, and Andrew Wyeth. The site of the museum itself exists within three historic buildings—the Charles Shipman Payson Building, the McLellen House, and the L. D. M. Sweat Memorial Galleries. PMA displays its collection throughout these interconnected galleries and hosts a range of educational and cultural activities as well.

Allagash Brewery

Allagash Brewing Company, Portland

With a goal of hand crafting the best Belgian-inspired beers in the world, Allagash Brewery continually pushes the limits to keep their status as one of the most famous breweries in Maine. A tour of the brewery takes visitors from the beginning stages of the craft all the way to the bottling room, where you see the machines and people of Allagash working together to turn out a great product. At the end of the tour, Allagash offers a tasting of four beers, including the famous Allagash White. Check into the gift shop at the end of your visit to see a place full of every Allagash branded item you could dream of, including a few different varieties of beer that are only available on site. The brewery also hosts seasonal events, locally and in other U.S. states, that can be found on their website. Allagash Brewery is also a family-friendly environment, boasting a fun, stimulating, and supportive experience for all.

Casco Bay Islands

The Casco Bay Islands are sometimes called The Calendar Islands, as there are so many you could explore a different island almost every day of the year. The islands offer visitors a chance to enjoy a slower pace of life—exploring nature, watching for wildlife, relaxing on beaches, and admiring works of local artists. Peaks Island houses a thriving artist community, restaurants, and sandy beaches, while Great Diamond Island is home to the historic grounds of Fort McKinley. Other notable stops include Long Island’s large conservation area with nature trails and Cliff Island, known as the smallest year-round island of the Casco Bay, with dirt roads good for bicycling. The Casco Bay Lines offers year-round ferry service to the larger islands, so if you are planning an excursion it might be a good idea to check out their online schedule. No matter which island you choose, the variety that Casco Bay has to offer will satisfy the adventurers as well as those looking for a more leisurely pace.

Eastern Promenade

The Eastern Promenade is a historic 68.2-acre public park and recreation area in Portland, Maine. Rated as a top thing to do on TripAdvisor, the Promenade offers great views of the harbor’s activities overlooking Casco Bay and a variety trails for walking, running, or biking. Sunrise overlooking the Casco Bay Islands is a notable sight, but if you are not an early riser, the views during the day are just as spectacular. Whether you prefer to sit on a bench and enjoy the peaceful surroundings, or feel a need to get out and enjoy the waterfront trail, the Eastern Promenade offers a breath of fresh air away from the city. The East End Beach on the Promenade offers swimming and a public boat launch, as well as public toilets and changing areas during the summer months. Kayaks and canoes can also be stored on rental racks and launched from the beach or the boat ramp.

Old Port

The Old Port is a historic district of Portland, Maine, known for its cobblestone streets, 19th century brick buildings, and fishing piers. While the coastal town has its history, the area is also a center of activity good for shopping and entertainment with a selection of boutiques, galleries, restaurants, and bars. If you take a walk at the water’s edge along Commercial Street you can see a great view of the working waterfront. The smell of the sea air, the sound of the foghorn on a distant lobster boat, and the chatter of seagulls flying above all add to the quaint charm of the coastal atmosphere of the Old Port. A few other features to note are Portland’s City Hall built by Carrere and Hastings (best known for their design of the New York Public Library), as well as Portland High School, the oldest standing high school in the United States.

Portland Observatory

Since it was built in 1807, the Portland Observatory has offered spectacular views of Portland’s busy harbor and served as a beloved symbol of the city’s rich maritime heritage. Existing as the only remaining historic maritime signal tower in the United States, the Portland Observatory was recognized as a National Historic Landmark in 2006. Guided tours focus on maritime history, the purpose and importance of the structure, and changes in Portland over the last two centuries. The tour of the tower ends at the top of the stairs with spectacular views of Portland, Casco Bay, Back Cove and Mount Washington. A gift shop located at the base of the Observatory has a collection of postcards, books on area architecture and local history, posters, children’s toys, and other gifts related to Portland’s history. For the history buff, the Portland Observatory is a must-see location, with a tour full of fascinating historical tidbits and a view well-worth the climb.

Portland Head Lighthouse

Though not situated in Portland itself, the Portland Head Light is an iconic landmark of the Casco Bay area. Located in Cape Elizabeth, Maine, the light station sits on a head of land at the entrance of the primary shipping channel into Portland Harbor. Commissioned by George Washington and dedicated by the Marquis de Lafayette, the Portland Head light was first lit in 1791 and is the state’s oldest lighthouse. The Museum at Portland Head Light is located in the former Keepers’ Quarters and contains a number of lighthouse lenses and interpretative displays. Fort Williams Park, in which the lighthouse is situated, is open from sunrise to sunset, so even if you don’t make it to the museum, the historic landmark can be easily seen and photographed from many areas within the park. With beautiful views of the rugged Maine coastline and the lighthouse as the centerpiece, the Portland Head Light area is a great place to enjoy the fresh air, crashing waves, and a little piece of Maine’s history.

Arts District

Located just a few blocks from the waterfront, Portland’s Arts District has been re-imagined from the original department store shopping area to be home to some of Portland’s renowned museums and galleries like the Portland Museum of Art and the Children’s Museum and Theatre of Maine. The Arts District also houses the Maine College of Art (MECA) as well as attractions like the Salt Institute of Documentary Studies, Cross Insurance Arena, the renovated State Theatre, Portland Stage Company, the Maine Historical Society, Museum of African Culture, and the historic Merrill Auditorium for performing arts. The funky vibes of this downtown area emanate from the collection of museums and art galleries mingled with numerous contemporary music and performance venues, plus some fine and ethnic dining choices. A walk through this part of the city will immerse you in some of the contemporary culture of Portland, a full display of the arts native to the area.

DeLorme Map Store

Located just north of Portland in Yarmouth, Maine, the Delorme Map Store is more than just a store—it is the headquarters of the famous DeLorme mapmakers and home to the world’s largest rotating globe, Eartha, which can be viewed from the store’s three levels. While Eartha is the eye-catcher of DeLorme, the store offers a rich assortment of travel planning items, guide books, globes, maps and atlases covering the entire world. For the tech enthusiasts, DeLorme offers top-of-the-line GPS software and accessories, plus some unique geocache trackables and a selection of geography toys and learning games for kids of all ages. Whether you are an adult or a child, the selection of gadgets that DeLorme has to offer will bring out the kid in you anyway. One look at Eartha, the world’s largest globe, and the excitement of entering a world of maps will be more than enough to hook you in.

Culture Trip Summer Sale

Save up to $1,395 on our unique small-group trips! Limited spots.

Edit article