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 www.bostonharborwalk.com 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.
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