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
The 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
Follow 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
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
In 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.
Eats
Boston 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.
Stay
The Boston Harbor Hotel is the city’s only Forbes Five-Star waterfront hotel. The 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
Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributes travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She is fluent in Italian and Spanish and laughably adequate in French. Her background as an Early Childhood Educator gives her an added understanding of what it takes to travel with kids in tow. She firmly believes that the most important part of education takes place outside of the classroom, on the road, around the world. She never misses a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. Follow Allison at @gourmetrav.
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram