Maine’s main city, Portland, is situated along Casco Bay’s southern coast. The area was formerly known as Machigonne by the indigenous peoples; it was later developed by British colonists in the early 17th century and swiftly grew into a significant fishing and trading port.
Visitors can now cruise the Old Port neighborhood’s cobblestone alleys, explore the pier, which is still humming with activity, or spend days exploring the Arts District’s museums, galleries, concerts, and antique shops.
There are many activities available on the water as well, including fishing charters, whale-watching excursions, and sightseeing cruises around the bay and the Calendar Islands. Portland Sea Dogs games, which are played by the Boston Red Sox’s AA affiliate, are entertaining for both sports fans and families.
Plan your sightseeing and fun with our list of the top things to do in Portland, Maine.
Portland’s Old Port District & Commercial Street
The Old Port neighborhood of Portland, Maine is located in the center of the city. It is a busy downtown with lots to do that has managed to keep its old-world charm. Tourists can board one of Portland’s numerous ferries, sightseeing cruises, or charters to the Calendar Islands and other locations around the shoreline.
The dock, which is situated on Commercial Street, is only a short distance from the Old Port’s cobblestone streets, which are home to historic structures, boutiques, restaurants, galleries, and other retail establishments.
The narrated sightseeing tour of Portland on a vintage fire engine offers a good overview of the city and offers a distinctive perspective on the Old Port neighborhood and other areas. Tourists get the perfect vantage point for taking pictures of Portland sites while perched on the engine.
Casco Bay and the Calendar Islands
The beautiful Calendar Islands are located in Casco Bay, where Portland is located. Officially known as the Casco Bay Islands, the moniker was given due to its sheer number; it has been said that you could visit a different island here every day for an entire year. There are a lot of huge and tiny islands to explore, even though this is not entirely accurate.
In addition to regular ferry service to Great Diamond Island, Peak’s Island, Chebeague Island, Long Island, and Cliff Island, other businesses offer scenic cruises to and around the islands.
The former Fort Mckinley is located on Great Diamond Island, and Long Island is renowned for its abundance of calm beaches and nature paths.
Golf on Chebeague Island and biking in several of Cliff Island’s smaller, less-populated areas are two more island pursuits.
Victoria Mansion
Henry Austin, a renowned architect, created the Victoria Mansion in Portland, also known as the Morse-Libby House, between 1858 and 1860. Ruggles Sylvester Morse, a hotel magnate from New Orleans, utilized this Italian villa-style estate as a vacation residence. The house is a prime example of Portland’s pre-Civil War extravagance.
The building is decorated with many intricate decorations, including rich linens, intricate wood carvings, plasterwork, gilded surfaces, and a sizable stained glass skylight. Unique carpets, silver, porcelain, and other ornamental antiques have all been kept in the house’s contents, which has been a museum since 1941.
Address: 109 Danforth Street, Portland, Maine
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Eastern Promenade
The Eastern Promenade Trail, which leaves from the Old Port neighborhood and follows a railroad track along the shoreline at Back Cove, is one of the most picturesque walking routes in the city. The 2.1-mile track meanders around the 68-acre Fort Allen Park, which is really divided into two parallel paved and crushed stone paths.
Numerous branches from the main trail lead to different areas of the park, some uphill to stunning viewpoints. The walk also leads to East End Beach, the only public beach in the area, and a popular picnic, swimming, and sunbathing place for locals.
For those arriving by boat, there is a boat launch nearby as well as canoe and kayak racks. There are restrooms near the beach as well as benches along the path. Leashed pets and bicycles are also welcome.
Portland Museum of Art
Fine and decorative arts from the 1700s onward can be found in the collection at the Portland Museum of Art. The museum’s holdings, which house more than 18,000 pieces, mostly consist of American and European paintings but also span a wide range of other mediums like sculpture, pottery, furniture, and other items. There are more than 650 pieces by Winslow Homer in total, including watercolors, etchings, and oil paintings.
The museum sells tickets for anyone who wants to visit the nearby Winslow Homer House. Major artists’ pieces, including those by Cassat, Renoir, Monet, Degas, Picasso, and O’Keefe, may also be found in the museum. Additionally, it showcases spotlight exhibitions of artists from Maine and regularly rotates its extensive collection. In addition to presentations by curators and lectures, the museum also hosts family-friendly events and activities.
Address: Seven Congress Square, Portland, Maine
Children’s Museum & Theatre of Maine
Portland’s children’s museum, one of the best things to do in the city with young children and toddlers, will return in 2021 in a brand-new 30,000-square-foot building. With greater room, the exhibits and programs have grown, but the goal hasn’t changed: to teach visitors of all ages about their environment via immersive experiences, hands-on learning, and dramatic role-play.
The Our Neighbourhood exhibit occupies an entire floor of the museum, where kids may pretend to be different people while learning about some of the varied lifestyles that make Maine unique. A farmers market, a fire vehicle, a railroad and station, a medical facility, and a lobster boat are all present in the area. There are many activities in Lighthouse Cove that are made specifically for babies and toddlers.
Climb, Crawl, and Slide is an indoor climbing structure including crawl-through areas for young children and a birds’ nest viewing tower for more experienced climbers. Visitors to the Dress Up Theatre can dress up and reenact stories in addition to seeing live performances. The airport contains a belt for moving luggage and a control tower with a live video feed from Portland International Airport’s tower across the river.
Address: 250 Thompson’s Point Road, Portland, Maine
Crescent Beach
The mile-long Crescent Beach is a part of Crescent Beach State Park, which is located on Cape Elizabeth just south of the city. It is bordered by dunes and forests and features some of Maine’s famous rock-bound shoreline. Boardwalks provide access to the beach through sea grass-covered dunes, enhancing the sense of seclusion. Offshore, fishing boats bobbling in the water surrounding a small island.
Families enjoy going to the beach because of the calm waves and relatively warm water, and the low rock outcrops create tidal pools that are ideal for kids to explore. In the summer, lifeguards are on duty. There are picnic sites, showers, restrooms, and a concession stand at the park. This charming park is well-liked all year round for beachcombing, cross-country skiing, strolling, and fishing.
Address: Bowery Beach Road, Cape Elizabeth, Maine
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Portland Observatory
The Portland Observatory, the only surviving example of an early maritime signal station in the United States, was constructed in 1807 to provide shipowners advance warning when their ships were approaching the harbor.
The 86-foot tower’s top was equipped with a powerful telescope that allowed sailors to see ships up to 30 miles out to sea before they could be seen from the harbor. Lemuel Moody, an ambitious former ship captain who also built the observatory, paid shipowners a fee to notify them when their ship was going to land so the owner may be prepared to unload at the docks.
Up until 1923, when the two-way radio rendered it obsolete, the Observatory served as a functional marine signal tower. In 1939, the tower underwent restoration and reopened as a historical artifact from the Age of Sail. On the National Register of Historic Places, it is listed. There is plenty of time allotted for viewing during tower tours.
Address: 138 Congress Street, Portland, Maine
Maine Narrow Gauge Railroad Co and Museum
The Maine Narrow Gauge Railroad Museum is a terrific site to visit on a wet day in Portland because it works to educate the public while preserving the heritage of the two-foot-gauge railway. The museum has a number of vintage coaches, kid-friendly activities, and historical narrow-gauge railroad exhibits.
On the narrow-gauge line it maintains, the museum also runs a picturesque train ride that travels three miles roundtrip and explores the Eastern Promenade. From May to October, the train runs, and it’s a great opportunity to see Casco Bay and take in the scenery. During the 35-minute journey, knowledgeable guides offer commentary and are glad to answer inquiries about anything from local history to wildlife.
Address: 58 Fore Street, Portland, Maine
Portland Head Light & Fort Williams Park
Lighthouses are not only used as physical landmarks for boats; they have also come to represent Maine and are familiar features in the majority of coastal communities. Portland is not an exception, since it has a number of lighthouses that date all the way back to 1871.
Portland Head Light in Cape Elizabeth, Maine, is among the most popular due to its excellent museum, breathtaking views of Casco Bay and Portland Harbor, and proximity to four other lighthouses.
Portland Head Light in Cape Elizabeth, Maine, is among the most popular due to its excellent museum, breathtaking views of Casco Bay and Portland Harbor, and proximity to four other lighthouses.
Fort Williams, which also shares the promontory with the museum, is featured in many displays and relics there. At Fort Williams Park, visitors can explore the old fort structures and take advantage of the recreational amenities.
Address: 1000 Shore Road, Cape Elizabeth, Maine
Wadsworth Longfellow House
General Peleg Wadsworth, the great-grandfather of well-known author Henry Wadsworth Longfellow, finished construction on the Wadsworth Longfellow House in 1786. Here, the author spent his formative years, and his sister lived there until her passing in 1901.
The property was left to the Maine Historical Society as part of her will, and it has been meticulously conserved, including almost all of the original furniture and domestic furnishings, both beautiful and functional.
Since 1962, the house has been recognized as a National Historic Landmark. It stands out on Commercial Street as a brick time capsule. Visitors should allow time to take a trip through the garden, which the Longfellow Garden Club designed in the Colonial Revival architectural style in 1926.
Address: 489 Congress Street, Portland, Maine
Fort Allen Park
The 10-acre Fort Allen Park is a stunning location for viewing the passing boats because it is located above Casco Bay. It was initially constructed in 1775 during the American Revolution as a fort to protect the port, and it was expanded during the War of 1812. Today, people enjoy going there for walks, picnics, and summer performances in the bandstand. It’s a lovely location to view the sunrise for those that get up early.
There are a few monuments throughout the park that are worth finding. A cannon that was recovered from the USS Maine after it sank in Havana port in 1898 and the rebuilt main mast from the World War II cruiser USS Portland is also there, in addition to a monument commemorating the American Civil War. The seven victims from Maine are commemorated on a memorial for the September 11th, 2001 terrorist assault.
Address: Eastern Prom Boulevard, Portland, Maine
Southworth Planetarium
The University of Southern Maine’s Portland campus has a dome theatre that is home to the Southworth Planetarium, which hosts astronomy presentations, educational lectures, and evening classes. The planetarium offers a wide range of programs, including engaging adventure shows that take viewers to new worlds and presentations for the center’s youngest guests.
The 360-degree screen is also utilized to transport viewers to Mars, the Hubble telescope, and even a wild journey through our solar system. Traditional stargazing astronomy shows are also available. Other programs and courses cover subjects including meteorology, the connection between astronomy and mythology, and dinosaurs.
Address: 70 Falmouth Street, Portland, Maine
International Cryptozoology Museum
Both believers and skeptics will agree that Portland’s International Cryptozoology Museum is the city’s most unique attraction. In fact, it claims to be the only one of its kind in the world — a museum dedicated to the study of unknown or hidden animals.
The museum is home to a variety of fossils, models, creative interpretations, records, and first-hand stories of many legendary creatures, making it unquestionably one of Portland’s most interesting attractions.
Purported hair samples from enigmatic creatures, like the Abominable Snowman, Bigfoot, and a Yowie, are among the most valued objects on the show. Additional displays examine the evidence and folklore surrounding numerous species, including the Montauk Monster, the Jersey Devil, thylacines, lake monsters, and thylacines.
Address: 11 Avon Street, Portland, Maine
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Image Credits: Portland, Maine