Last Updated on March 22, 2023
The seaside city of Portland is Maine’s largest metropolitan vacation destination. This historic city gracefully mixes vibrant culture, great shopping, gourmet cuisine, and outdoor recreation with breathtaking natural surroundings. Just a ferry away, you can visit islands, forts, and lighthouses.
Henry Wadsworth Longfellow, a native of Portland and one of the best 19th-century American poets, wrote a poem about the beautiful city in “The City by the Sea.”
Today, you can see much of the 19th-century architecture and landmarks of this fishing settlement town with a fast-growing urban center.
The Old Port
This port is one of the main attractions of Portland. Every year the port handles over 206,000 international passengers, including 41,000 cruise ship passengers.
This port is one of the few working waterfront ports in the United States, being New England’s largest tonnage port and second largest fishing port. This port is also the largest inbound transit tonnage port in the United States.
Here you can have stunning views of the ocean while enjoying the colorful boats, old streets and buildings, and the authentic fishing piers. This port has a wide variety of shops and restaurants.
Commercial Street
This street in the historic tourist district is a working waterfront and the downtown main street of Portland. Here you will see fishing boats, lobster pots, and fishing gear mixed with dockside condominiums and offices, as well as tourists visiting boutique shops and restaurants.
The street is well known for its unique character, strong sense of place, and the mixture of uses involving marine and fishing industries with modern life.
Food Lover’s Paradise
Thesmell of baked goods floats out onto the streets. The port’s local seafood scene with the classic fresh oysters and lobsters is impressive in its own right. Now mix that with international gourmet options and craft beers, and it’s no wonder Bon Appétit magazine namedPortland the 2018 Restaurant City of the Year.
If you go, please try some of the best donuts I have ever eaten at The Holy Donut. Donuts are proudly made out of Maine potatoes, but they also have gluten-free options. Bon Appétit said that The Holy Donut was “alone worth the trip to Portland.”
Catch a Lobster
Portland offers its visitors the opportunity to see how lobsters are caught in several tours on the waters of Casco Bay. I went with The Lucky Catch tour company. The tour lasted around 90 minutes, where I experienced the real adventure and hard daily work of a Maine lobsterman and began to understand how this delicious food gets to my plate.
You can also admire the picturesque lighthouses, historic civil forts, and seal rocks.
Some tour companies will boil your lobster catch for dinner at one of their partner restaurants for a real catch to table experience.
Peak Island
Peak Island is only a 20-minute ferry ride away from Portland. It was a popular destination in the late 19th century, then known as the Coney Island of Maine, for all the hotels, theaters, cottages, and amusement parks.
Today, the small island is home to around 1,000 people, increasing to 2,000 during the summer months. Several beaches and outdoor activities like hikes, as well as the pleasant ferry ride, make it a beautiful day trip.
The Portland Observatory
This tower is the last remaining maritime signal tower in the United States. It stands as a symbol of Portland and it has the best view of the city and Casco Bay.
Built in 1807, this octagonal, lighthouse-shaped building was used to monitor the harbor. Former sea captain Lemuel Moody’s job was to tell ship owners when their vessels arrived at the port.
This historic landmark is open to the public from late May until mid-October. You can buy tickets at the entrance. The observatory has two levels, one with all the historical facts of maritime life in the city as well as the magnificent view of Portland and Casco Bay. You can choose between a self-led tour and a guided one with an observatory volunteer eager to answer your maritime questions.
First Friday Art Walk
On the first Friday of each month, historic downtown Portland invites you to explore the creative community and local artists of Maine, from Biddeford to Bangor, Portland to Presque Isle.
This self-guided evening tour from 5 p.m.to 9 p.m. allows visitors to visit galleries, artist studios, exhibits, museums, and special receptions around town. City streets also come alive with theatrical performances and dances.
During your walk, you can observe an artist work as well as participate in hands-on workshops. Visit Art Walk Maine to see a schedule of events.
Munjoy Hill
If you like to explore and wander on your own terms, Munjoy Hill neighborhood is your destination in Portland. In the high ground at Portland’s east end, it was settled in 1930 by working-class immigrants making their living on the waterfront. This neighborhood was known for its roughness and close community.
In the 1990s, artists and entrepreneurs brought new restaurants, condos, art galleries, and boutiques to the neighborhood, mixing historic Portland with the contemporary hipster scene. Today this popular area has distilleries like the Maine Craft Distillery and award-winning restaurants like the Drifter’s Wife.
Perusing shops and a walk by the Easter Promenade make a perfect evening in Portland.
Maine Historical Society and the Wadsworth-Longfellow House
This is the first home museum in Maine and it was named as a National Historic Landmark in 1962. Once home of the beloved American poet Henry Wadsworth Longfellow and his family, the house was thoroughly restored in a five year project from 2002.
Today, this house transports you to19th century life in all its glory with decoration trends, furnishing designs, artifacts, sculptures, portraits, and family life.
Tours are self-guided, and an app is available with an audio description of every room. The gift shop provides you with Maine and Longfellow specific items like books of poetry and souvenirs. The house is impressive to every visitor. Don’t forget to visit the spectacular gardens.
Portland Museum of Art
The Portland Museum of Art is the oldest public art institution in the United States. Founded in 1882 as the Portland Society of Art, this small museum is the home to pieces from well-known artists like Claude Monet, Andrew Wyeth, Winslow Homer, Andy Warhol and Edward Hopper, among others. The museum has permanent exhibits highlighting local and international artists. Tours are available, but must be booked in advance.
The highlight of this museum is the collection of work by local artist Winslow Homer. Some of his most famous pieces like “Weatherbeaten” and “Sharpshooter” are on display.
The museum blends three building styles: the Federal style, three-story mansion built in 1801; the Beaux-Arts style gallery built in 1911; and the modern building design by I.M. Pei.
The gift shop has art souvenirs. The museum also has an outstanding café catered by Black Tie Company, a very well-known caterer in Maine. Pastries at the café will reflect the museum’s current exhibits, art even in cookies.
Portland Head Lighthouse
This lighthouse is the oldest and most beautiful lighthouse in New England. Situated along the impressive shores of Forth Williams Park, this lighthouse is owned, managed, and conserved by the town of Cape Elizabeth.
Portland Head Lighthouse dates back to 1791. You can learn more about its history at the museum located in the former keeper’s house. A historical timeline guides the tour from the origin of the lighthouse, the life of its keepers, technological changes, and the militia activities in Fort Williams. You can also learn about the decommissioning and automation of the lighthouse in 1989.
The museum has a gift shop with beautiful lighthouse and Maine related souvenirs. The museum and shop are open daily in the summer and weekends only in the off-season.
Fort Williams Park
After visiting the most photographed lighthouse in Maine, take time to explore Fort Williams Park. The history here is visible. It started as a military installation in 1873, and in 1899 was formally named Fort Williams. The fort was ready for battle in the Spanish-American War, but the facilities were never used. It served as an active destination for housing and training troops until it was decommissioned and closed in 1963.
In 1964, Cape Elizabeth purchased the 90-acre property. Today, this is a popular park for tourists, hikers, bicyclists, walkers, and artists for the beautiful Portland Head Lighthouse.
During the summer, several events take place here, like races, family days, and the Labor Day Art Show. It is a great park to explore and see nature with the lighthouse and ocean backdrop.
The park is free and open to the public 365 days of the year.
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