Portland’s best hidden or historical places: Staff Picks

  • Portland Observatory Photo by Jeff Roberts

  • U.S Custom House Photo by Irvin Serrano

  • Portland Masonic Temple Photo by Irvin Serrano

While some are well known, these locales offer glimpses into the past or escapes from the present. 

Portland Observatory

The over-two-centuries-old Munjoy Hill landmark is the only known remaining historic maritime signal tower in the United States. The observatory, open to the public for tours starting in May, was used to help incoming merchant ships communicate with the docks before arriving with their cargo.

U.S. Custom House

The granite exterior of the U.S. Custom House, constructed between 1867 and 1872, makes the building a noticeable landmark near Portland’s waterfront, but inside is more impressive. Granite flooring is laid out in a checkerboard pattern, and an eight-foot, walnut, pedestal-mounted counter with a spherical clock stands in the center.

Portland Masonic Temple

The Portland Masonic Temple looks nondescript from the outside—there isn’t much to distinguish it from office buildings on the block. Yet, once inside, majestic meeting rooms and halls used by the fraternal organization unfold, many of which the public can now use.

Glickman Library’s Great Reading Room

Although many patrons at the University of Southern Maine’s library are students, anyone can use its resources. Those include the seventh- floor reading room—a quiet, inspiring room with furniture from Thos. Moser and wide- angle views of Back Bay.

Portland Freedom Trail

Looking to learn some lesser-known Portland history while exploring the Old Port? This self- guided tour covers sixteen sites associated with the Underground Railroad and includes information about prominent figures in Portland’s anti-slavery movement.


St. Luke’s Cathedral’s Courtyard

Karen Duddy, an advertising account manager for Maine Media Collective, recommends visiting this State Street church’s courtyard as an escape. “I found it by chance and would sit from time to time, especially when I was having a bad day,” Duddy says. “Just a peaceful place, and you feel a thousand miles away. That spot is like a secret garden…an oasis.”

Wilde Memorial Chapel

This chapel near the southeastern edge of Deering’s expansive Evergreen Cemetery is used for both weddings and funeral services. The granite building’s architect, Frederick A. Tompson, also designed the castle in Deering Oaks park and another staff pick—the Masonic Temple.

Former Press Herald Tunnel

When the Portland Press Herald and its printing plant were located on opposite sides of Congress Street—the Press Hotel now resides in the newspaper’s former space—workers used an underground tunnel to go between the buildings. The tunnel isn’t open to the public, but it still exists.

Western Cemetery

“You can spend hours there,” says Chris Kast, brand director at the Brand Company, of the cemetery near the Western Promenade. “It is full of history and sparks some amazing conversations regarding life in Portland way, way back when.”

Fort Sumner Park

Nestled in the Munjoy Hill neighborhood, the site of a former fort now offers a popular vista for residents in the area. Benches look out on the city to the west, making for magnificent sunset views.



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