The 5 Most Charming And Walkable Downtowns To Visit In Massachusetts

As one of the oldest states in America, Massachusetts exudes an old-world charm that is truly its own. This spills into many of its small towns, which are filled with colonial architecture that transports you back in time. Whether you want to escape Boston for a more intimate environment or find yourself drawn to the lure of leaf peeping in the Berkshires, there are so many quaint, charming New England towns to visit.

Choosing the state's five most charming and walkable downtowns was difficult, but I used my own experience as a Massachusetts native, coupled with research in the r/Massachusetts subreddit to get more local perspective to narrow it down. In the end, these five beautiful destinations are a great representation of what small-town Massachusetts has to offer. Scattered across the state, they each have a walkable downtown area that really makes visiting them a pleasure. From the historical sites of Concord that surround a town center full of shops, restaurants, and art galleries, to the underrated charm of Maynard, these towns have so much to offer.

Massachusetts is also so well connected that it's easy to enjoy time in any of these cities. Boston Logan International Airport will be the gateway for many people, though the state is also served by numerous regional airports that can land you within striking distance of any part of the state. So, if you are looking for a place where you can enjoy an authentic, bustling downtown on foot, look no further than these gems of New England.

Located just 30 minutes northwest of Boston, the historic Massachusetts town of Concord is known both as the birthplace of the Revolutionary War and as a hub for some of the 19th century's great literary minds. This rich history adds another layer of meaning to the small town's bustling downtown area. Concord's center is a compact area starting at Monument Square and running down Main Street, where visitors can enjoy everything from antique shopping to viewing the six National Historical Landmarks that are located within the area.

For antiquing, North Bridge Antiques and Thoreauly Antiques, both located on Walden Street, are filled with delightful treasures ranging from jewelry to antique books and everything in between. For small bites and coffee, local residents in the r/Massachusetts subreddit singled out Concord Cheese Shop and Haute Coffee as great selections. With a deli counter and a small selection of wines, Concord Cheese Shop is the perfect place to fill up a picnic basket before taking the 20-minute stroll to Old North Bridge, where the Revolutionary War began. Here, you'll find beautiful gardens for relaxing while also getting a fill of American history.

The nice part about Concord is that you don't even need a car to arrive, as the town is located on an MBTA commuter rail line with regular service to Boston. Concord's train station is just half a mile on foot from the town's charming shops and restaurants on Main Street, making it a delightful day trip using public transportation.

Perhaps best known for Tanglewood, the summer home of the Boston Symphony Orchestra, the town of Lenox is a haven in the Berkshires with a delightfully charming downtown area. Nestled in western Massachusetts, Lenox's compact town center showcases its history while offering plenty of dining, shopping, and cultural attractions. Stroll the tree-lined streets sipping a drink from the casual Lenox Coffee or join a Saturday afternoon wine tasting at Dare Bottleshop & Provisions, which specializes in organic wines.

Within a 1-mile radius, visitors can enjoy the colonial architecture of historic attractions like Lenox Academy, which was established in 1803 as the county's first secondary school, and the early 19th-century Curtis Hotel, a stunning brick building that speaks to the town's role as a destination for well-off New Yorkers during the Gilded Age. Those who really want to dive into the era will want to visit Ventfort Hall, a Gilded Age mansion transformed into a museum celebrating the era, just a half-mile walk from Main Street.

While lovers of the arts will certainly enjoy Tanglewood, there are plenty of other cultural activities within walking distance in Lenox. This includes Sohn Fine Art, a downtown art gallery specializing in contemporary photography. Rounding out the experience includes perusing Lenox's unique boutiques, whether it's the home decor and cashmere throws at MacKimmie Co. or leather goods at Berkshire Classic. Located just 45 minutes from Albany by car, this charming town on the Massachusetts/New York border is a beautiful retreat from the hustle and bustle of city life.

When researching the r/Massachusetts subreddit for locals' thoughts, one town continued to be mentioned: Maynard. Located in central Massachusetts, this small town of about 11,000 residents has a thriving, walkable downtown that pays homage to its past while looking to the future. The whole town is just a little over 5 square miles, and it comes with a fascinating past as a thriving mill town during the Industrial Revolution thanks to its strategic location on the Assabet River. 

The historic mill, now a mixed-use office building, sits in the heart of Maynard, anchoring the charming town center. Less than a half-mile away you'll find Sanctuary, a live events and cultural space. This former Congregational church is now a thriving music venue with a packed calendar of events. Just around the corner, ArtSpace is a former middle school turned cultural center with artist studios, workshops, and exhibitions to bring arts into the community. Maynard even has its own movie theater, which was founded in 1949. After a renovation in the 2000s, Maynard Fine Arts Theatre continues to show first-run films on its three screens.

When you're feeling peckish, Maynard offers a host of international restaurants within a short walking distance. Choose from Smack Noodle, the town's ramen bar with a rating of 4.7 stars on Yelp, or tuck into some tapas at Azucar Tapas Bar. These are just a couple of the many eateries situated on Main Street, making it easy to find something for everyone. Located just 25 miles northwest of Boston, Maynard is easily reachable by car and makes a great, uncrowded destination for a bit of culture in a small town. As an added bonus, the town is surrounded by parks and wildlife refuges so you can incorporate a hike into your visit.

Salem may have gained notoriety for its infamous 17th-century witch trials, which bring visitors in droves during the Halloween season, but the historical coastal city, located just 20 miles north of Boston, is fantastic year-round. Served by the commuter rail from Boston, it couldn't be easier to reach Salem and start exploring. The town's train station is less than half a mile from the well-known Essex Street Pedestrian Mall.

The cobblestoned thoroughfare area sits right downtown and is a great place to walk without worrying about cars. While it can get very crowded in October it's perfect for shopping and dining if you visit at the right time of year. One visitor on Tripadvisor enthusiastically writes, "This place is the spot in Salem! A beautiful outdoor pedestrian mall with all the shops, bakeries, coffee shops, places to eat, bars & historical buildings in Salem to enjoy!" But Salem's downtown is more than just the pedestrian area. Art lovers can visit the Peabody Essex Museum, which houses a strong collection of American and Asian art. And, of course, there are classics to visit in town, like the Salem Witch Museum.

Seasonal happenings, like the Artists' Row, a rotating marketplace of artists and creatives that runs from May to November close to Old Town Hall, are other ways that the community keeps a vibrant downtown area. There's also plenty to eat and drink, whether you want some New England seafood at the highly rated Turner's Seafood or Ledger, which sits inside a historic 19th-century bank building and puts a modern twist on classic New England cuisine. With so much to do in such a compact space, Salem certainly has one of the best walkable town centers in Massachusetts.

Our list of the best walkable downtown areas in Massachusetts wouldn't be complete without a town located on Cape Cod. The staple of New England, where locals flock in droves throughout the summer, has many charming towns but none quite as unique as the one located right on its tip. The New England gem of Provincetown is a beloved destination for its inclusivity (it's one of the top LGBTQ+-friendly small towns in America) and its artsy vibes. Visitors can arrive to Provincetown using seasonal 90-minute ferries that depart from Boston or a 30-minute flight from Boston via Cape Air. In the offseason, it's just a two- to 2.5-hour drive from the city.

Provincetown, also affectionately known at P-town, has a vibe all its own. Founded as a sleepy fishing village, it became a haven for art and culture from the turn of the 20th century. Commercial Street runs for 2.5 miles and is the thriving heart of downtown, with endless amounts of shops, restaurants, and art galleries. Though it can get quite crowded during the summer months, between the pedestrians and the pedicabs, it's still a delightful stroll, particularly if you take local advice from the r/CapeCod subreddit and visit during the fall. 

So, what is there to see and do during your stroll on Commercial Street? The Provincetown Art Association and Museum (PAAM) with its year-round exhibitions and events, as well as a permanent collection of American art, is a great way to dip your toe into P-town's art scene. MacMillan Pier is the destination for boating enthusiasts who want to enjoy the boats docked at Provincetown Marina. If waterfront dining is on your to-do list, downtown Provincetown has a plethora of options, including Fanizzi's Restaurant and The Red Inn, which are both known for their incredible seafood.

Born and raised in Massachusetts, it was a true pleasure highlighting some of the state's most beautiful and walkable town centers. Using my own personal experience in visiting towns like Provincetown and Maynard, as well as drawing on local viewpoints in the r/Massachusetts subreddit, I was able to narrow down an extensive list to just five selections.

To do so, I not only took into considerations like the number of shops and restaurants in a 1-mile radius, but also looked for cultural offerings like theaters, artist studios, and monuments that bring a unique flair to each town. These conditions helped in identifying downtowns that are both walkable and charming. I also aimed to spread the selections out geographically, selecting towns that span the entire state, from the Berkshires to Cape Cod.