If ever a town was born from the sea, it would be Portland, Maine. It’s big enough to offer a modern art and culinary scene, yet small enough for old, maritime charm. Portland has something for everyone with its incredible museums, restaurants, breweries, water tours and scenic beauty. It’s ideal for both walking and water tours. As an Acupuncturist-at-Sea I visited many of the world’s best ports, and this is one of my favorites! So, read on to learn about Portland Maine attractions.
About Portland, Maine
Portland is on a peninsula extending into Casco Bay, an inlet to the Gulf of Maine. Furthermore, Casco Bay is home to 6 lighthouses and 8 historic forts. Portland is the ideal balance of natural beauty and culture with endless things to see and do. It has a thriving art and culinary scene with many galleries, museums, restaurants, craft breweries and historic sites.
Being a seaport, Portland is also known for its lobster and outdoor recreational activities, such as, fishing, sailing, swimming and kayaking. It’s home to the preppy, fleece company, L. L. Bean and the late 19th century landscape painter, Winslow Homer. Also, the poet, Henry Wadsworth Longfellow lived in Portland expressing it in “The City and the Sea.”
Portland is great for walking tours because it’s compact and picturesque on the peninsula. Its 7 neighborhoods include the historic Old Port, Waterfront, The Art’s District, West End, East End, East Bayside, Riverside and Parkside. Maps are helpful in planning out a path of exploration for anyone.
15 Portland Maine Attractions
by Neighborhood
Old Port
Old Port Culinary Walking Tour
This 3-hour foodie delight is a great opportunity to learn about Portland’s history. In this walking tour the guide takes you to restaurants and pubs in the Old Port. Here you can learn about the Maine-inspired cuisine, such as, lobster, honey wine, craft beers and chocolate truffles made with potatoes.
Shop at Seabags
This Seabags flagship store is on the waterfront’s Commercial Way. This unique and sustainable business handcrafts eclectic bags from sail masts. The nautical-themed bags, totes and accessories are meticulously designed and crafted. None of their materials are imported, and they’re 100% recycled. I shopped there and think they are tastefully vibrant and fashionable.
Holy Donut
It’s worth the long line for the Holy Donut experience, almost like an initiation for the Portland tourist. On the waterfront, this is a great way to start the day with Maine’s premiere potato donuts and coffee. There are many flavors to choose! And the coffee is fantastic too. Don’t miss out on the selfie at the window with wings to commemorate the Holy Donut experience.
Waterfront/Water Tours
Casco Bay Lines Ferries
This ferry system allows you to go island hopping in the scenic Casco Bay. It’s open daily and goes to the following islands: Peaks Island, Little Diamond Island, Great Diamond Island, Long Island, Chebeague Island, Cliff Island and Bailey Island. If you only see one island, check out Peaks Island. It is known for its charm, history, beaches and scenic beauty. Many people enjoy the island for outdoor activities, such as, biking, kayaking and swimming.
Lucky Catch Cruises
Here’s the ultimate way to learn about lobstering and see the sites along the way. Lucky Catch Cruises offers private tours and cruises in the summer for passengers to observe the lobster catching process. There is scenic cruising of lighthouses, forts and the Portland skyline. Some tours include a Lobster Bake on Peaks Island.
The Arts District – Portland Maine Attractions
Portland Museum of Art
The Portland Museum of Art provides an incredible collection of more than 22,000 artworks with some big names. Every Friday from 4 – 8 pm, admission is free. The famous Maine artist showcased here is the 19th century Landscape painter, Winslow Homer. His painting, Weatherbeaten (1894) is the most popular piece of art in the museum. It depicts the high tide at the height of a storm.
Additionally, the museum displays works from European artists of the impressionism and surrealism movements. For example, Edgar Degas, Claude Monet, Edvard Munch, Auguste Rodin and Pablo Picasso are here.
Maine Historical Society/Longfellow House & Garden
The Longfellow House and Garden is affiliated with the Maine Historical Society (MHS) next door. The MHS offers guided tours of museum galleries and the Longfellow House. It’s best to check beforehand at MaineHistory.org because tour times are limited.
The 19th-century Henry Wadsworth Longfellow lived his childhood in Portland. He is known for his famous poem on “Paul Revere’s Ride.” His home and garden are open as a museum with tours from May – October. The garden in the backyard is lovely and dedicated to his family. It includes plants that are native to Maine and written about in his poems and writings.
The week before Halloween the home is open for a haunted house tour, based on Longfellow’s poem, “Haunted Houses” and family members that died in the house.
East End
Portland Observatory
On Munjoy Hill this National Historic Landmark is the only maritime signal tower still open in America. It is 86-feet tall and used as a museum and observatory. With no basement, the rock ballast on bottom floor and octagonal design keep the structure standing during storms The cupola’s balcony views are the most far-reaching in the city, showing Mt. Washington on a clear day.
East Cemetery
Established in 1668, this is the oldest historic site in Portland. With about 4,000 graves no one has been buried there since 1858. Many important historical figures are buried here. There are Guided Walking Tours by the non-profit group Spirits Alive from June to October. The cemetery is especially scenic in the autumn with the colorful leaves next to the old tombstones.
Eastern Promenade
This 2.1-mile scenic and historic paved trail goes along the waterfront of Portland. It follows an old railroad track and includes benches, picnic tables and beaches. The views are fantastic of Casco Bay and historic, beautiful mansions on other side. Near the cruise terminal is the East End Beach, Fort Allen Park and Maine Narrow Gauge Railroad Company & Museum.
Take a Vintage Train Ride
Near the cruise terminal is the Maine Narrow Gauge Railroad Company & Museum. This vintage train ride takes you back in time on a 3-mile, 40-minute tour along the Eastern Promenade. It offers special events, such as, Rails & Ales Sunset Trains, Ice Cream Trails and Polar Express.
West End
Victoria Mansion
This National Historic Landmark is a 19th-century home known for its gorgeous architecture. Its elaborate interior remains 90% intact and preserved. The mansion connects history lovers with the past, including interesting stories. Also, there’s a gift shop with Victorian Era and made in Maine goods. It is open May to October and offers guided tours of the interior.
Other Must-See Sites & Things to Do
Visit Lighthouses
From the 60 lighthouses in Maine, Portland has 4 in Casco Bay. Portland Head Light on Cape Elizabeth is the oldest in Maine and the most beautiful. It is next to Fort Williams Park with scenic trails and rocky points to explore the awesome views. Additionally, in Portland are the Spring Point Ledge Lighthouse, Portland Breakwater Lighthouse (Bug Light) and Cape Elizabeth Light.
Eat Lobster
Maine Lobster is known for being especially delicious, mainly because the cold, Atlantic waters make the meat more tender and sweeter. The culinary scene in Portland for seafood and lobster is thriving. So, don’t miss out when there on some of the world’s best lobster.
Popular restaurants for lobster in Portland are Porthole, Lukes and Highroller Lobster Co. I loved my experience on the pier at Lukes, voted Portland’s Best Lobster Roll in 2023.
Beer-Tasting Breweries
Portland is known for having a flourishing craft beer scene. There are numerous breweries and beer selections to choose from. Many are on the East Bayside and Riverside. For example, popular breweries are the Allagash Brewing Co., Bissell Brothers Brewing Co., Austin Street Brewery, Battery Steele and Brewing, Shipyard Brewing Co.
Portland Freedom Trail
The Portland Freedom Trail is a self-guided walking tour in mostly the Old Port and Arts District. This 2-mile (3.2) km trail stops at 15 points of interest related to African Americans. It starts at Franklin Street Wharf and ends at Mariner’s Church.
Many sites are linked to the mid 1800’s Underground Railroad, leading to freedom in Canada or England. The Abyssinian Meeting House is the third oldest African American meetinghouse in the U.S.
Enjoy Portland, Maine!
There is so much to see and do in historic Portland, Maine. Even if you only have a short time, the Old Town is a concentrated area to experience tons of culture and natural beauty. Leave comments below if your travels take you to Portland. Let us know any tips or ideas on how best to experience this amazing city!
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