Walk This Way: The 4 Best Walks in Boston

Boston puts its best foot forward in summertime. Compact and brimming with attractions, it’s an excellent walking city, especially with a warm breeze nipping at your neck. To really soak in the cityscape and connect with both its historic and contemporary sides, your legs are the best method of transportation. Ready, set, go explore Boston’s best walking trails on you next visit. 

1. The Rose Kennedy Greenway

Rose Kennedy Greenway - BostonThe Rose Kennedy Greenway is a mile-and-a-half sliver of urban park that winds its way through the heart of Boston. It’s a multi-purpose space with art installations, food trucks, an open-air wine garden, fountains and much more. Lively summer programming includes free yoga and tai chi instruction. The 17 acres of organic landscape are maintained without the use of pesticides or harmful chemicals. This wonderland of flora includes everything from three types of bamboo to formal perennial beds to countless beautiful blooms. It’s also home to a colony of Italian honeybees. 

The Pollinator Ribbon was introduced in 2016 in an effort to attract and support pollinator species. It provides bees, butterflies, wasps and birds with nectar and pollen from three-season flowering plants. 

2. The Freedom Trail

The Freedom Trail - BostonFollow in the footsteps of our founding fathers on the Freedom Trail. A walk along this 2.5-mile red brick path sheds light on this city’s pivotal position during the American Revolution. It traverses 16 historically significant sites including leafy Boston Common, America’s oldest park, and the Bunker Hill Monument, site of the Battle of Bunker Hill, the first major battle of the American Revolution. Take a self-guided walk or join one of the Freedom Trail Foundation-led group tours.

3. HarborWalk

Boston Harbor Walk

HarborWalk is a 43-mile nearly continuous park hugging Boston’s shoreline. If you’re considering strolling a section, choose the vibrant Seaport District’s mile-and-a-half long urban loop as it meanders along the water’s edge. Stroll past the stunning Institute of Contemporary Art and the interactive Boston’s Children’s Museum. Watch the sailboats, paddle a kayak or catch a ferry and discover the Boston Harbor Islands, dozens of islands that offer a rich array of recreational options.  

4. The Black Heritage Trail

The Black Heritage TrailIn Beacon Hill, the Black Heritage Trail is a 1.6-mile path that offers the chance to discover the history of Boston’s thriving 19th-century African American community and the leadership role it played in the Abolition Movement. Established in the late 1960s, trail highlights include several stations that were part of the Underground Railroad. Free guided tours are offered by the National Park Service or pick up a map for a self-guided tour at the Museum of African American History located at 46 Joy Street.


Seafood in BostonBoston may be a pedestrian’s paradise but there’s nothing pedestrian about its food scene. When hunger strikes head to Nebo for a culinary treat. The owners, sisters Carla and Christine Pallotta, were born and raised in the North End, Boston’s Little Italy.  If the food at Nebo tastes like something your nonna might have made, that’s because the menu of rustic Italian dishes is straight from their own mother’s recipe book. The pasta is perfectly al dente, the service charming and the casual space welcoming. At lunchtime, order one of the hearty and delectable sandwiches, called Spuckies. Desserts are splurge-worthy. 


Boston Harbor HotelThe Boston Harbor Hotel is the city’s only Forbes Five-Star waterfront hotelThe Rowes Wharf waterfront location is a dream, close to nearly all attractions and across the street from the Rose Kennedy Greenway. Sweeping views of Boston Harbor, fabulous service and countless amenities account for the hotel’s popularity. If you’ve got sore muscles from all that walking, the hotel’s top-notch spa offers a variety of soothing massages.

If that isn’t enough to entice you, the Boston Harbor Hotel hosts the annual Summer in the City entertainment series. Free live music and movies in the moonlight are scheduled every Tuesday-Friday night all summer long. 

Get to Boston from NYC

The above walks are an easy stroll from Boston’s South Station, where Amtrak and buses drop passengers off. You can find more details in our Manhattan to Boston Transit Guide.

For additional information, visit www.Bostonusa.com

Photo credits: Featured image courtesy of Kyle Klein. Additional images Kyle Klein, Freedom Trail Foundation, Boston Harbor Hotel, Nebo