Walking Boston  by Robert Todd Felton

Walking Boston Guide Book

by Robert Todd Felton (Wilderness Press)
Walking Boston  by Robert Todd Felton
Boston is a walker’s town. It’s as clear as the brick red path marking the Freedom Trail, the bright blue signs of the Harborwalk, and the green of the Emerald Necklace series of parks. Boston’s nearly 400-year history has led to the development of hidden neighborhoods, historic sites, and iconic parks that tempt both Bostonians and visitors out onto the sidewalks, paths, and trails lacing this close-knit city. In addition, the Big Dig project, which helped revive downtown and the waterfront by moving Interstate 93 underground, has created an energy and excitement that has driven projects like the Harborwalk and the Rose Fitzgerald Kennedy Greenway. Walking Boston offers the best of Boston’s new and old rambles. This portable guide features detailed maps, original photos, and public transportation information for every trip.

© 2013 Robert Todd Felton/Wilderness Press. All Rights Reserved.

Trails from the "Walking Boston" Guide Book
Displaying trails 20 of 34.

Displaying trails 1 to 20 of 34.

Home to trendy boutiques and upscale shops, this buyer’s boulevard is well stocked with art, fashion, and food. Just be sure to bring all your spare change—and maybe a piece of plastic or two. During the summer, the sidewalks fill with strolling shoppers and sightseers, creating a lively and pleasant atmosphere. If it gets too hot, duck into one of the stores or galleries to cool off.
Boston, MA - Mountain Biking,Walking - Trail Length: 2
Combining three great art collections with cheerful park strolls and a bit of history, this walk begins at the Museum of Fine Arts and wanders the paths of the Back Bay Fens, a bucolic park lining the banks of the Muddy River. The route returns via Huntington Avenue and the Massachusetts College of Art, with a stop for afternoon tea at the Isabella Stewart Gardner Museum.
Brookline, MA - Birding,Hiking,Trail Running,Walking - Trail Length: 2.25
It has been known by many names—the Church Street District, South Cove, and Kerry Village—but Bay Village is the name that endured. By whatever name, this 6-block neighborhood is one of Boston’s best-kept secrets. Stumbling into Bay Village can feel a bit like wandering onto a 1930s movie set. The well-kept brownstones and cobblestone streets make the neighborhood seem like a smaller, less-ornate version of Beacon Hill. Wandering among the quiet, tree-lined avenues, you may have a hard time believing you’re still in the heart of Boston, just steps away from the Common.
Boston, MA - Walking - Trail Length: 1
San Francisco has Nob Hill, Manhattan has Park Avenue, and London has Belgravia—neighborhoods where heritage, architecture, and money are inextricably linked. For Boston, it’s Beacon Hill, a maze of cobblestone streets and well-kept row houses arranged along Beacon Hill between Storrow Drive and the State House. The neighborhood is a National Historic District, an elite enclave of privilege, and a vibrant community, all in one. It’s the type of place where you can live just down the street from both the Museum of African American History and U.S. Secretary of State John Kerry.
Boston, MA - Walking - Trail Length: 2
This walk starts at Suffolk Downs—where trainer Tom Smith discovered the famous racehorse Seabiscuit—and then explores lovely Belle Isle Marsh, with views of Winthrop Island and Logan Airport. The paths are clear and easy to follow, so this tour makes a wonderful, easy stroll if you are looking for a bit of nature in East Boston. Inside the visitor center, you can see one of the original steam-driven pumps from the 1890s and learn more about the history of the island. Continue toward the southernmost tip of the island, traversing in the shadow of a cluster of 150-foot-tall oval-shaped tanks. These are the sludge digesters, which busily process 3 million gallons of wastewater.
Winthrop, MA - Walking - Trail Length: 2
Belmont Hill, in the town of Belmont, is one of those neighborhoods that you hear about but rarely see firsthand. At less than 5 square miles, Belmont is almost exclusively residential, with only a small commercial row on Pleasant Street. With the well-heeled Belmont Hill School and Massachusetts Audubon’s Habitat Wildlife Sanctuary dominating much of the remaining acreage, it’s no wonder that this charming enclave may just like being slightly off the beaten path.
Belmont, MA - Walking - Trail Length: 3.75
Boston is nothing if not a college town. With nearly 40 colleges and universities, academic campuses are easy to come by. But Boston College is unique for its wooded hills, pleasant reservoir, and glimpse of the Boston skyline. Founded in 1863 by the Society of Jesus, Boston College opened in 1864 with a mere three teachers and 22 students. By the beginning of the 20th century, the school had outgrown its Boston campus, and construction of the Chestnut Hill campus began in 1909. By 1913, the college had opened the first building on the new campus, Gasson Hall, and moved completely out of Boston. Today, the Chestnut Hill campus covers 130 acres, and Boston College has 752 faculty and more than 14,000 students.
Brookline, MA - Walking - Trail Length: 3
In the first half of the 19th century, Boston was a hotbed of cultural activity, especially for Transcendentalism, a loose set of beliefs and projects that emphasized humankind’s inherent connection to God and to each other. This tour covers one of the most famous of the Transcendentalist projects—an ill-fated utopian society known as Brook Farm. Beginning in 1841, a group of intellectuals and laborers followed Unitarian minister and Transcendentalist visionary George Ripley into the wilds of West Roxbury to live according to the movement’s ideals and the practices set out by French utopian socialist Charles Fourier. Although the farm attracted the attention of Ralph Waldo Emerson and Henry David Thoreau and a young novelist named Nathaniel Hawthorne (who lived at the farm for half a year), it suffered an early demise in 1846 when its largest building burned to the ground. Now the 179-acre farm is protected as a National Historic Landmark and managed by the state Department of Conservation and Recreation.
Needham, MA - Walking - Trail Length: 1
Nestled against an industrial port, Castle Island and Pleasure Bay nonetheless offer miles of pleasant beach paths with views of sailboats and windsurfers. This walk starts at a historic fort and continues along a breakwater populated with people fishing for bass or just enjoying the view. The tour then loops back along the beach to the starting point—a terrific place for ice cream.
Boston, MA - Walking - Trail Length: 2
The Charles River separates Boston from its smarty-pants cousin Cambridge to the north. This walk bridges that gap and features some of the best of both sides. Beginning in Boston’s West End, the walk follows greenway on both banks to keep you close to the water, shopping, and myriad outdoor recreational opportunities.
Boston, MA - Walking - Trail Length: 4
This section of the Charles River is less crowded and less showy than the Esplanade and the river basin near the Museum of Science, and it’s also more relaxing and peaceful. Perhaps because of that, this area attracts strolling lovers, sunbathing students, and river-watchers who indulge in quiet contemplation on benches along the banks. Also keep an eye out for crew teams from the local schools knifing through the water.
Cambridge, MA - Walking - Trail Length: 3.5
When the English settlers first arrived in Massachusetts in 1629, they set up camp in Charlestown, favoring its sloped hills and ocean views. They couldn’t locate any freshwater on the peninsula, however, and soon moved across the water to start the city of Boston. Later, in 1775, Charlestown’s historical legacy was cemented when a ragtag group of volunteer soldiers inflicted some serious damage on the army of the British Empire.
Boston, MA - Walking - Trail Length: 3.25
Looks can be deceiving. Boston’s Chinatown may look small, but it is the third-largest such district in the country (behind only San Francisco’s and New York City’s Chinatowns). While perhaps overshadowed by the city’s better-known Italian North End or the Irish neighborhoods of South Boston, this little gem offers great tightly packed streets, colorful architecture, and an intriguing history going back hundreds of years. The short distances of this walk allow plenty of time for window-shopping and sampling from any of the Cambodian, Vietnamese, and Cantonese restaurants crammed along the streets.
Boston, MA - Walking - Trail Length: 1.25
Jutting into Dorchester Bay, the University of Massachusetts Boston campus offers lovely views of the South Shore and Quincy’s Squantum neighborhood. But while the walk along the water is refreshing even on the hottest of days, the real hero of this walk is the John F. Kennedy Presidential Library and Museum, a wonderful repository of not just presidential records but also an important collection of Ernest Hemingway’s papers.
Boston, MA - Walking - Trail Length: 2.5
The long, wide avenues of Boston’s Back Bay are no accident. Built on mud flats, the neighborhood was designed as a showcase for Boston’s wealth, with Commonwealth Avenue the proud centerpiece. From the Eliot Hotel at one end to the statue of George Washington at the other, Commonwealth is the grand face that Victorian Boston built to display its wealth and respectability to the world. It is also the crucial link in the Emerald Necklace series of parks running from Jamaica Plain to Boston Common.
Cambridge, MA - Walking - Trail Length: 2
This tour begins with a library, meanders through malls, and swings through a domed sanctuary called the Mother Church. From a brass hare to a glass globe, there is plenty to take in and, given the number of shops, perhaps even more to take home.
Boston, MA - Walking - Trail Length: 2
Call it egg-celent, or perhaps sh–tty, but this tour around Boston’s iconic wastewater-treatment plant is as rich in history, spectacular views, and pleasant walking paths as it is free of any olfactory evidence of its unique location. The walk circles the island, taking in views of Boston to the west, the harbor islands to the south, Massachusetts Bay, and Boston’s North Shore. The paths, part of a 60-acre park ringing the sewage-treatment facility, are a cheerful, happy use of an island that has been home to much suffering—having served as a quarantine for the mentally and physically sick, a prison for the convicted, and a place of forced internment for the innocent.
Winthrop, MA - Walking - Trail Length: 3
In the early 19th century, Boston was the undisputed cultural capital of the United States. Publishing houses, bookstores, and meeting spaces brimmed with revolutionary philosophy and radical literature. This walk mixes that wonderful historical pedigree with the vibrancy and energy that make Boston such an interesting city today. And to fuel all the thinking this route stimulates, the trip ends at one of the nicest places in town for dinner.
Boston, MA - Walking - Trail Length: 1.25
Once the home of shipbuilders, merchants, and a cattle ranch, East Boston is now a wonderfully vibrant multiethnic community. (It’s also the site of Boston’s Logan International Airport.) This area saw difficult times in the 1980s and ’90s, but recently it has received significant interest and investment. This walk circles East Boston’s Maverick Square, sampling the best of the neighborhood, from an eco-oriented affordable-housing project to a lovely waterfront park on a reclaimed pier.
Boston, MA - Walking - Trail Length: 3.4
Boston’s literary and cultural history may be rich, but for many Bostonians, the real historical treasure of this town is the Red Sox, whose baseball stadium just so happens to be the oldest in America. Indeed, the history of Fenway Park and the Red Sox is the stuff of legends: Babe Ruth’s “curse,” Ted William’s spectacular home run well into the right-field bleachers, the Red Sox 2004 comeback against the Yankees to win the American League Championship en route to their first World Series victory in nearly a century. It’s a magical place. New Englander and writer John Updike describes Fenway Park the best in the opening of his story about seeing Ted Williams’s last game at Fenway, calling the stadium “a lyric little bandbox of a ballpark,” offering “a compromise between Man’s Euclidean determinations and Nature’s beguiling irregularities.”
Cambridge, MA - Walking - Trail Length: 1.25