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Ten lesser-known stretches worth visiting in Beantown.

October 09, 2015

Most visitors to Boston might roam around the Freedom Trail for an afternoon, or take a saunter around the Common and the Public Garden. But if you’d like to go in a different direction, we’ve got some under-the-radar walks to offer. After all, this is America’s most pedestrian-friendly city, and these secret stretches will make you see it like never before.

Longwood Avenue

Amidst the bustle of Longwood Avenue’s many medical institutions, there’s much to admire here. You can pay a visit to the Warren Anatomical Museum and spend a few moments people-watching in front of Harvard University’s Medical School campus on their well-appointed grand lawn.

Bay State Road

Once the home of Boston’s most proper residents, this expansive road contains a myriad of gorgeous brick buildings, many of which are now part of Boston University’s campus. Make sure and stop by The Castle, which is an elaborate Tudor Revival mansion to take a look at its lavish interior.

Shawmut Avenue

A stroll down Shawmut Avenue in the South End is a perfect way to explore the area’s distinguished Victorian architecture. Wander through nearby Blackstone Square to look over its lovely fountain, which is decorated with playful dolphins.

William J. Day Boulevard

Originally called the Strandway, William J. Day Boulevard leads curious pedestrians along some of South Boston’s finest beaches. Make your way around to Castle Island to take a tour of Fort Independence, which has stood guard over Boston for over 160 years.

Mt. Vernon Street

To walk the length of Mt. Vernon Street on Beacon Hill is to truly take a step back in time. With period streetlights and cheek-to-jowl stately brick homes, it’s particularly marvelous to wander during twilight. Don’t forget to walk around nearby Louisburg Square, which is surrounded by Greek Revival homes.

Hemenway Street

Truly charming Hemenway Street is the connective tissue between the Fens and the Back Bay. As you walk along it, you might hear a bit of coloratura from an open window at the Boston Conservatory or see folks enjoying a peaceful moment in Forsyth Park.

Dartmouth Street

The bustle of Dartmouth Street offers up an embarrassment of cultural riches, including views of H.H. Richardson’s Trinity Church, the Boston Public Library’s main branch, and the stunning statuary of the Commonwealth Avenue Mall.

Centre Street (in Jamaica Plain)

Follow the gentle curve of Jamaica Plain’s Centre Street to find bookstores, tiny boutiques, and more. Gather strength or finish off the day with sangria and tapas at Tres Gatos.

Park Drive (Back Bay Fens)

Take a long walk along Park Drive to experience master landscape designer Frederick Law Olmsted’s eye for details. As part of this excursion, you’ll pass by elaborate rose gardens, the Fenway Victory Gardens, and the Holy Trinity Orthodox Cathedral.

Mount Auburn Street (Cambridge)

Prim and proper, Mount Auburn Street is one of Cambridge’s greatest thoroughfares. A leisurely journey will take visitors from such stalwart’s as J. Press (look out for Harvard scarves and bow-ties) all the way through Harvard Square to the distinguished pastoral setting of Mount Auburn Cemetery.

Max Grinnell covers Chicago, Boston, and a few more beats for Travel + Leisure. You can follow him on Twitter

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