Jogging and Biking in Boston Esplanade

Boston’s Best Urban Adventures

Connect the best of Boston’s historic sites and iconic views with these hiking, biking and running routes though the city.

Live somewhere long enough, and you’re bound to start taking the elements for granted that give the place its magic. The antidote, of course, is to look at them from a new perspective. And when it comes to Boston, whether you’re newly arrived or learning the city’s history for the first time—or just trying to better understand and appreciate your own backyard—there’s no better way to do it than via human power. The following three urban adventures each connect a sampling of Boston’s most famous historic sites. From a bike path that traces Paul Revere’s ride to a running loop tagging three iconic Boston views, these routes will enhance any visit or at least help you see your hometown in a whole new light.

Run: The Boston Trifecta 

Just shy of 6 miles, this road-running loop connects three of Boston’s most iconic attractions (Fenway Park, Boston Common, and the Charles River) via a system of verdant greenways. Along the way, you’ll pass the famous Good Will Hunting Bench in Boston’s oldest public garden, cruise by the spires of Trinity Church, and encircle the fragrant Kelleher Rose Garden.

To do the loop, start in Boston Common (if you’re taking the T, get off at the Boylston Stop). Head east to enter the Boston Public Garden. Here, you’ll jog around clockwise (keep an eye out for swans in the lagoon) until you gain the Commonwealth Avenue Mall, a long strip of tree-lined walks and monuments that stretches a little over a mile. 

At the end of the mall, head south through Charlesgate Park and loop through the Back Bay Fens until you get to the rose garden. Here, head north to skirt around the Fenway Park field and try to catch a whiff of Cracker Jack and fresh-cut grass. Just northeast of the field, use a pedestrian bridge to cross Storrow Drive and gain the Charles River Bike Path. A little over a mile later, you’ll use another bridge to exit the bike path. This will take you south back toward Boston Public Garden and the start of the loop. 

Hike: Spectacle Island Tour 

It can be tough to find good hiking within the heart of any city, and Boston is no exception. But the Harbor Islands offer a unique workaround: Made up of 34 distinct islands, this national and state park is home to some of the city’s best hiking routes—and some of its most interesting historical sites.

As one of the least developed islands, Spectacle offers quiet trails and a small summit that affords sweeping views of Boston Harbor. From the top, you can see Fort Independence (built in 1634 by the British) as well as Thompson Island, which was an important trading post in the 1800s. You’ll also get views of Deer and Long islands, both of which were the traditional homelands of Native American residents before European settlers turned them into concentration camps in the 1600s.

To see it all on a short day-hike (just 2.3 miles), take the ferry from downtown. Loop around the island going clockwise, summiting North Drumlin before descending to the south and circling back to the wharf.  

Ride: The Minuteman Bike Way 

You may not be able to gallop a horse through downtown Boston to reenact Paul Revere’s famous ride, but a two-wheeled steed is certainly fair game on this bike path. Designed to approximate Revere’s route, the Minuteman Commuter Bikeway is just over 10 miles long and traces an inactive railroad cut from Bedford to North Cambridge. Along the way, you’ll follow the shore of Spy Pond, roll right past the Lexington Battle Green where the famous Revolutionary War skirmish took place, and skirt the Bedford Depot, a testament to Boston’s rich railroad history. 

If you’re using the T to get to the start of the route, take the red line to Alewife. You can either take buses to get home, or retrace the route for a 20-mile out-and-back ride.

All articles are for general informational purposes.  Each individual’s needs, preferences, goals and abilities may vary.  Be sure to obtain all appropriate training, expert supervision and/or medical advice before engaging in strenuous or potentially hazardous activity.