9 of the Most Walkable Towns in Massachusetts

Massachusetts is a state of first steps, as evidenced by the famed pilgrims who first touched ground at Plymouth Rock in 1620, ripe from a long Atlantic voyage on the Mayflower. These days, the state is much more traversable than the water-logged forests it once was, thanks to intentionally designed suburbs that wrap around opportunity-rich main streets. Yet, “walkable” is more than just efficient pedestrian routes to essential goods— it is a way of life that fosters community interaction. So, live your best life and stride through these gorgeous towns today.

Concord

Twenty-five square miles is no mammoth space to patrol when it is evident that Concord is lined by forests and rivers between suburbs that dawdle and curl around its developed hubs. Even those living at the farthest corners could get by on foot (or bicycle if in a hurry) when it comes to accessing essential goods on the Main St connecting Concord and West Concord.

The colonial alley style matches the environment well around the Main Streets Market & Cafe, and these brick facades truly put the “England” back into “New England.” Like most of the towns here, the cuisine, culture, and shopping options are easily praised, but the layout and aesthetic of Concord deserve kudos of their own.

Lexington

Lexington is a masterclass in suburban design: weaker neighborhoods feature grid patterns that are efficient yet brutalist, or spiderwebs that are chaotic and dangerous when vehicles are involved. Instead, Lexington opts for neighborhoods that conveniently converge on a central main street with libraries, a Thai Kitchen, a bistro, and other necessities like a children’s center and Family Dental.

Green spaces are king when it comes to defining “walkability,” so the Lexington Battle Green Park is the pulsing heart of the Lexington community, and golf courses, farms, and adorable trails are dispersed evenly between residential areas. The high school is also central, so no student is disadvantaged by a 5-mile walk compared to other peers who live closer, and sports fields and tennis courts are less than a block away. After all, walkability does not have to mean “pilgrimage.”

Northampton

A quiet town of less than thirty thousand, something about Northampton just feels like home. Steeples and bakeries line its central thoroughfare, which is spacially the opposite of claustrophobic. For those lucky enough to occupy an apartment above a shop like Meriyem’s Cafe or Ted’s Boot Shop, every day must be like strolling into a small-town television show. And stroll these pedestrians do— the Three Country Horse Show and Fairgrounds are less than a fifteen-minute walk away, and the Smith College Japanese gardens are less than a mile away to the west.

For other folks, residences occupy the majority of space between those “downtown” shops and the Big Y World Class Market/Walmart/Big Lots department stores a mile and a half away. However, those looking for a moment of reprieve will revel in the Rainbow and Riverbank roads, which peacefully trail beside the magnificent Connecticut River; one can even wave to folks doing the same on the opposite side during a clear day.

Amherst

Many know this academic town for hosting one of the Little Ivies, “Amherst College,” and it goes without saying that university students with countless academic options ultimately are convinced by a quality town and environment.

Recreation and conservation areas, such as Mill River and Wildwood, are handsomely proud enclaves for poets and dreamers who have had the privilege of walking here for centuries. That said, the quiet cemeteries are a privilege to visit because they contain the names and stories of people who literally built the foundation of New England and, daresay, the United States, so they are wonderfully curated places for distant relatives and respectful visitors alike.

Wellesley

Wellesley offers Bostonians (the city conveniently sits less than 10 miles away) a rare opportunity to lounge in the sun at spots such as Morses Pond beach; a tan is a valuable sight in the northeast, after all. Lake Waban, with mother geese parading their trophy goslings close behind, is a quarter mile away from Morses Pond if a change of scenery is needed.

Another appeal for those who like to keep their commutes pleasant and close is that Roche Bros, the primary supermarket, is squarely in the middle of town, just behind Linden St, which hosts the majority of shops and bakeries. Quite a few K-12 schools and colleges are sprinkled throughout, so parents need not be concerned about young ones trotting a path with their friends rather than taking a bus.

Ipswich

For a modest community of approximately 14-thousand, 10 square miles of water area is a remarkable amount, but seeing as Ipswich is on the coast, the math adds up. Speaking of which, the duly named Ipswich Bay hosts miles of idyllic sandy shoreline, which take the cake in afternoon strolls. Observation boardwalks with coin-operated binoculars afford curious gazers a chance to spot a roaming sailboat or a creature prowling the sandy grass dunes at Plum Island State Park.

Regarding the town, the majority of citizens occupy a central zone two miles inland up the Ipswich River. Hiking trails, bridges, and railroads crisscross the area, which means there is always a corner for the curious to sniff away at while stretching their legs with pets.

Marblehead

To the southwest, Marblehead occupies a peninsula that reaches out into the Atlantic. History is a specialty of this region, which lies adjacent to the infamous Salem and within walking distance of the Peabody Essex Museum. Its own historic district is crammed with fantastic architecture from eras long ago and the occasional beachfront or lighthouse.

A pedestrian-friendly bridge connects the mainland town with an island that hosts parks like Castle Rock and Chandler Hovey. This unique island safeguards a wildlife sanctuary at its heart that is praised by local guides for bird spotting, with species like the Yellow Crown Night Heron making nests throughout the trails.

Rockport

Over in Essex County, Rockport is a creative haven occupying coastal forests. Art shops and music centers take center stage on Main St, but iconic saltwater taffies from Tuck’s Candy & Gifts are nothing to pass-up, either.

Within just a few leaps and bounds, Front Beach and Back Beach Landing offer safe places to swim and relax in Back Harbor, and the perfect lunch can be cooked up at The Fish Shack Bar & Restaurant for an afternoon of delights, no car needed. For some last bonuses, Rockport also has a Community Cinema right by a train station that sits amongst hardwire, grocery, ice cream, and other useful venues.

Belmont

For the last stop on this tour, Belmont is a remarkable pick. Arguably, Belmont comprises the benefits from the majority of the other towns, such as a bustling central plaza with pizza shops and sporting goods, while also not neglecting mindful citizens by hosting a regular farmers market in a dedicated space right by the main thoroughfare, Leonard St.

Personality-wise, Belmont is a refuge for bookworms, artists, the pious, and those who need to disappear into the forest to bask in sun rays under a leafy green canopy now-and-then. Incredibly, amongst all the other attractions, Belmont residents managed to fit three luxurious golf courses in the corners of the town as well, and why drive a cart in a town so perfect for wandering on foot?

Final Thoughts

In contrast to the pedestrian-resistant “stroads” that make an afternoon walk both confusing and dangerous throughout America’s frontiers, Massachusetts has refined the fine art of a pleasant afternoon on foot. Historically, this reality makes sense as Boston itself is considered one of the most walkable cities in America, and the same talent that maintains this reality has ensured the same for elsewhere in the state, a fact highlighted by these remarkable towns. Grab a comfy outfit and some quality shoes because it is time to meet the neighborhood.