Things to Do in Portland, Maine, United States: Walking Guide

Portland, Maine, is a historic harbor city with museums, maritime landmarks, distinctive architecture, and island communities across Casco Bay. The best things to do in Portland, Maine, range from exploring the Portland Museum of Art and Victoria Mansion to discovering Fort Gorges and the unusual Umbrella Cover Museum. Neywo offers a free audio guide for Portland, Maine, with 37 narrated places.

What to see in Portland, Maine

Fifth Maine Regiment Community Center

On Peaks Island, the Fifth Maine Regiment Community Center—now known as the Fifth Maine Museum—explores how Civil War veterans remembered their fallen comrades. Built in 1888, the building served both as a memorial and as a reunion hall for surviving veterans. It is now open as a museum.

Fort Gorges

Fort Gorges rises from Hog Island Ledge in Casco Bay. Construction took place between 1858 and 1865, but changes in military technology made the fort obsolete before it could be used. No battles were fought there, and no troops were ever stationed at the former United States military fort. Today, it is a park accessible only by boat.

Portland Observatory

The Portland Observatory stands in the Munjoy Hill section of the city. Built in 1807, it is the only known surviving tower of its type in the United States. Observers used a telescope and signal flags to communicate with ships at sea, allowing messages to pass between ship and shore before vessels reached the docks.

Henry Wadsworth Longfellow Monument

At the corner of State and Congress Street, the Henry Wadsworth Longfellow Monument commemorates the poet. The public monument stands in Portland’s West End and gives its name to the surrounding Longfellow Square.

United States Customhouse

The United States Customhouse, also called the U.S. Customs House, stands at 312 Fore Street in downtown Portland. Built between 1867 and 1872, it was designed to house offices of the United States Customs Service. The building was listed on the National Register of Historic Places in 1973.

Children’s Museum of Maine

At Thompson’s Point, the Children’s Museum of Maine—also known as the Children’s Museum and Theatre of Maine—offers interactive exhibits and hands-on activities for children and families. Its displays encourage young visitors to discover, play, and engage with the world around them.

Wadsworth-Longfellow House and Maine Historical Society

The Wadsworth-Longfellow House is the historic house and museum where the poet grew up. It has been recognized as a National Historic Landmark since 1962 and was added to the National Register of Historic Places in 1966.

The nearby Maine Historical Society, the official historical society of the state, preserves collections, research resources, and places connected with Maine’s past. Together, the house and society provide a close look at Portland’s literary and local history.

Maine Narrow Gauge Railroad Museum

The Maine Narrow Gauge Railroad Museum combines a railway museum with a two-foot narrow gauge railway. Its track gauge is two feet, or 610 millimeters, offering a focused look at this particular form of rail transport in Portland.

Neal S. Dow House

The Neal S. Dow House, at 714 Congress Street, was built in 1829 for Neal Dow, a politician and prohibitionist who lived from 1804 to 1897. Dow wrote the first prohibition law passed by the Maine legislature, in 1851. Laws of this type later became known as “Maine law.”

Portland Fire Museum

The Portland Fire Museum occupies the former home of Fire Engine 4 at 157 Spring Street. Operated by the Portland Veteran Firemen’s Association, the museum explores the history of firefighting in Portland. Its location also reflects the association’s own history: after its former headquarters on South Street was demolished during construction of the Spring Street arterial, the association moved to this building.

Portland Museum of Art

The Portland Museum of Art is the largest and oldest public art institution in Maine. Founded in 1882 as the Portland Society of Art, it remains in downtown Portland, at the heart of the Arts District. The PMA is an important stop for anyone interested in Maine’s art and cultural life.

Umbrella Cover Museum

On Peaks Island, the Umbrella Cover Museum is devoted entirely to the humble cover that keeps an umbrella folded. Its collection turns an easily overlooked object into the subject of a museum and a tribute to the many ways umbrella covers can be made and used.

Victoria Mansion

Victoria Mansion, also known as the Morse-Libby House, offers a detailed portrait of lavish nineteenth-century American life. The downtown mansion was built between 1858 and 1860 in the Italianate style, with architect Henry Austin overseeing the project.

Its brownstone exterior, richly decorated rooms, opulent furnishings, and early technological conveniences are central to the experience. Giuseppe Guidicini and the New York decorating firm Herter Brothers worked on the interiors. Ruggles Sylvester Morse and his wife, Olive, lived in the house from 1860 to 1894. A preservation society acquired the property in 1940 and opened it to the public.

Cathedral of the Immaculate Conception

The Cathedral of the Immaculate Conception on Cumberland Avenue is a Gothic Revival Catholic cathedral and the seat of the Diocese of Portland. Built between 1866 and 1869, it was added to the National Register of Historic Places in 1985. For many years, it was Portland’s tallest building, a distinction that lasted until 2023.

Ram Island Ledge Light

Ram Island Ledge Light marks the northern end of the main channel leading toward Portland Harbor. The active lighthouse stands on Ram Island Ledge off Cape Elizabeth, in Cumberland County. It was listed on the National Register of Historic Places on March 14, 1988.

Explore Portland with a self-guided audio tour

A Portland, Maine self-guided walking tour lets you explore the city independently while following stories connected to the places around you. Neywo’s free audio guide includes three walking tours, one bus route, and one bike route, with 37 narrated places in total.

The walking tours are:

• Steeples and Spires of Congress Street: 1.86 km, 72 minutes, and 9 stops
• Mansions, Museums and Maine’s Poet: 3.08 km, 97 minutes, and 10 stops
• Munjoy Hill and the Eastern Promenade: 3.19 km, 94 minutes, and 9 stops

There is also one bus route:

• METRO Route 8: Around the Portland Peninsula: 13.1 km, 56 minutes, and 8 stops

And one bike route:

• Eastern Promenade Ride: 1.5 km, 8 minutes, and 5 stops

The app tells the story of each place as you reach it, at your own pace, with no group and no schedule. Narration is available in 11 languages.

Download Neywo and explore Portland, Maine

Download Neywo to discover Portland with a free audio guide that accompanies you through three walks, one bus route, and one bike route. Choose a Portland, Maine audio guide route, reach each stop when you are ready, and let the app tell you the story of the city around you—without a group or a schedule. If you are planning a wider trip through the United States, Portland is a distinctive place to begin exploring the country’s historic coastal cities.