date published: April 21, 2008

Panorama’s guide to tours, trails and great walks around Boston
by Josh B. Wardrop

One of Boston’s biggest claims to fame is that it’s one of America’s most walkable cities: two points that seem deceptively far apart can actually be traversed relatively quickly and easily on foot, and along the way you’ll see all that fantastic old architecture, beautiful urban streetscapes and greenspaces that you’d miss locked in a subway car or the backseat of a cab. So if you’re looking for some top-notch walks to take around the city of Boston—be they guided tours or strolls at your own pace—check out these recommendations, throw on some comfortable shoes and get moving!

Freedom Striders
If you’re looking for a walk that will stimulate your mind as much as your heart rate, then a journey along The Freedom Trail is just the ticket. One of Boston’s most popular activities for visitors, this 2.5-mile long trail encompasses 16 historic sites that were all vital and significant to the birth of our free nation. Beginning on Boston Common, the Freedom Trail (marked right on the ground as, alternately, a painted red line or a double line of red brick) winds through ritzy Beacon Hill past sites like the Massachusetts State House and Park Street Church, into downtown Boston past the Old Granary Burying Ground and the Old South Meeting House, past perennial Beantown center of commerce and history Faneuil Hall, into the historic North End, finally ending in Charlestown at the USS Constitution. And while many folks choose to explore the Freedom Trail on their own, the experience isn’t quite complete without taking a guided tour led by a Freedom Trail Foundation Player. These costumed interpreters tell all the stories of colonial Boston and explain each site’s relevance while in character as a historic figure from the American Revolution era. Refer to the freedom trail listings.

Lights, Camera, Action!
From Good Will Hunting to Mystic River to The Departed, lately it seems like Hollywood can’t get enough of shooting films in Boston. (In fact, Martin Scorsese and Leonardo DiCaprio are here again shooting another film, Ashecliffe. Think they like it here?) If you want to take a walk through the prominent Boston locations where those films, and many others, were shot, you’ll want to take a Boston Movie Tour (refer to tours listing). These guided, 90-minute walking tours show off all the spots you’ve seen in your favorite movies, while also spilling the dirt about the latest Hollywood gossip and info about new films in the works. Think of it like walking around the world’s biggest movie set—only it’s all real!

Touring for Tots
Okay, so walking isn’t always a child’s favorite activity. (Unless, of course, you want them to ride in the stroller. Then, they absolutely insist on walking!) If you’ve got a hankering to explore Boston on foot, turn to the folks at Boston By Foot (refer to tours listing). This tour company has walking tours of all designations, focusing on various parts of the city, and they’ve even designed a couple with small customers in mind. The Boston By Little Feet tour takes groups to see Freedom Trail sites, but presents them in a way that appeals especially to kids ages 6–12—pointing out, for example, sights like the copper grasshopper atop Faneuil Hall and the steaming kettle at Government Center. Or, you can purchase a treasure map, and lead your young ones on Captain Kidd’s Treasure Hunt. It’s so much fun, you’ll swear you’ll feel lighter on your feet.

Navigating the North End
The North End—Boston’s version of Little Italy—is one of the city’s most widely strolled neighborhoods, with folks drawn in by Freedom Trail stops like Old North Church, Paul Revere’s House and Copp’s Hill Burying Ground, as well as a stellar selection of Italian bakeries and restaurants. In addition to the general pedestrian foot traffic, though, there are a couple of organized tours that let people in on the secrets and delights of the “real” North End.

Local culinary expert Michele Topor’s North End Market Tours (refer to tours listing) provide foodies with expert insider tips on the best places in the North End to purchase everything from the freshest seafood and produce to the best cannolis in the city (according to Topor, it’s not Mike’s Pastry, despite those omnipresent boxes you’ll see people carrying). These three-hour tours even include delicious samples at some of the stops, so come hungry!

Meanwhile, the hidden history of the North End is unveiled by Guild Nichols on his popular North End Secret Tours (refer to tours listing). Nichols, who’s lived in the neighborhood for more than two decades, exposes visitors to fascinating historical stories that are rarely told, while pointing out sites like Rose Kennedy’s birthplace, doorways into secret catacombs and tunnels used by smugglers, the location of the narrowest house in Boston and much more.

Diversity on Display
Boston has always been a melting pot of disparate cultures, and a pair of self-guided walking trails offer a chance for visitors to explore the historical role that two particular cultures played in Boston’s evolution. The Boston Irish Heritage Trail (refer to tours listing) is a series of landmarks (20 in downtown Boston proper, and close to 50 more scattered in neighboring communities) that commemorate great Irish Bostonians or notable events in Boston Irish history, such as statues of former mayors Kevin White and John Michael Curley, memorials such as the Irish Famine Memorial and the Patrick Collins Memorial, and historic city landmarks like Fenway Park (built by Irishman Charles Logue) and the State House (built on the site of a prison used to house runaway Irish indentured servants) with unexpected Gaelic connections.

The Black Heritage Trail (refer to tours listing) is a series of landmarks that chronicles the struggles and triumphs of African-Americans during the early days of Boston. Guided tours through historic Beacon Hill—the neighborhood where most free blacks and escaped slaves lived—are offered by the Museum of African American History, or parties can take self-led tours to locations like the African Meeting House, built in 1806 and home to abolition meetings (as well as being Boston’s first black church), and the home of Lewis and Harriet Hayden, who harbored runaway slaves.

Expanding Boston’s Walkways
While Boston’s always scored as a great city for traversing on foot, recent years have seen even more parts of the Hub opening up to walkers thanks to a pair of ongoing development projects intended to provide pedestrians greater access to the outskirts of the city than ever before.

The Harborwalk—a planned 47-mile series of connected walkways tracing the Boston Harbor shoreline from Winthrop and East Boston in the north to Dorchester in the south—is close to completion, and has opened up beautiful seaside views to strollers from historic Charlestown down toward the North End and onto the South Boston waterfront. A walk along the Harborwalk offers great views of boats on Boston Harbor, picturesque offshore locales like Deer Island, gorgeous parks like Christopher Columbus Waterfront Park and cultural attractions like the Institute of Contemporary Art. Visit for maps of the Harborwalk and a full calendar of events.

Boston’s notoriously delayed and ultra-expensive “Big Dig” traffic project may have made us the butt of more than a few jokes nationwide, but it also brought us the lovely Rose Kennedy Greenway, named for the matriarch of Massachusetts’ renowned political family. This 15-acre ribbon of public walkways and vibrant, green parklands—created when the Big Dig converted the above-ground Central Artery into an underground tunnel, freeing up copious amounts of public land—connects all the way from Chinatown to the North End. Rather than sidewind their way through busy commercial districts (or cross a busy highway on foot!), people can now jog, walk or push strollers through the heart of downtown as they admire skyscrapers and the Boston waterfront, shop at urban markets or just sit and relax on a park bench.

back to homepage