10 Most Charming Town Squares In Massachusetts
Massachusetts, one of the oldest states in the US, is strongly influenced by colonial European culture due to the early Puritan settlements which were there in the 1600's. New England, the northeast region of the US where Massachusetts is located, has many ancient traditions that make it unique, one of which is the concept of a "town meeting," which required a central gathering place where residents would convene to discuss important issues. Over time, these spaces have evolved into the modern town square, now used primarily as an area for enjoyment and consumption of local goods, and Massachusetts has lots of them!
Concord
Twenty miles outside of the Massachusetts state capital of Boston, around eighteen thousand people call the city of Concord home. It is very significant to US history, since the first battle of the American Revolutionary War took place there in 1775 at the site of Concord's Old North Bridge, which is actually still there today in a restored form. In addition to historical sites, this city is full of vibrant architecture, museums, and nightlife. Concord is also highly relevant to US literature, having been home to several famous authors including Louisa May Alcott and Henry David Thoreau.
Concord's charming Monument Square is a huge part of the city's downtown social life. Like a typical town square, it has a green space with beautiful mature trees and in the center, a memorial statue for Concord's fallen soldiers. The square is a location for events like the Memorial Day celebration, and is surrounded by popular local businesses and attractions, being right beside the town's main drag. Within walking distance, you will find lots of things to do, like shopping at The Concord Bookshop, grabbing a drink at Haute Coffee, or buying a special piece at Artisans Way gallery.
Dedham
Also near Boston, Dedham is a mid-sized town which is often considered part of the capital's metropolitan area. It is a quiet suburban town with its own unique features that distinguish it from surrounding cities, such as the strong presence of preserved early American architecture, including the country's oldest surviving timber-frame structure, the Fairbanks House. Dedham was also the first town in the US to ever fund a public school with taxpayer contributions, and the first to build a man-made canal to connect two natural rivers.
Also unique to Dedham is its lovely town square, called Dedham Square, which is regarded as one of the best in Massachusetts. It has the fundamental vibes of a traditional New England town square, with visually appealing churches, boutique stores and other establishments circling it, plus a brand new curated outdoor space called the Town Green which was just finished this year, in 2025. Many locally recommended places in Dedham are located near the square, including the Dedham Summer Farmers Market, which runs June through October before switching to an indoor location. Big Bear Cafe and Espresso Bar, an independently owned coffee shop and eatery, and Eggs and Thai Cafe, a Thai restaurant, are two highly-rated food options in the vicinity of the square.
Hopkinton
Close to the large city of Worcester, Hopkinton is a smaller city of around eighteen thousand residents which offers a slower-paced lifestyle alongside proximity to bigger urban centers. It is said to be a fairly affluent town with a lot of outdoor recreation, including the scenic Hopkinton State Park with its accompanying Hopkinton Reservoir, as well as Whitehall State Park, which has its own namesake reservoir as well. This town is also well-known for being the start line of the famous Boston Marathon.
The town square in this city is the Hopkinton Town Common. It is a charming and intentional green space that hosts weekly events such as Sunday Concerts on the Common and Thursday Night Movies on the Common. The downtown strip along Main Street ends at the common, and is where many popular gathering spots of the city are located. One of these is Blue Square Pizza, a locally-owned sourdough pizzeria which is aptly named considering its proximity to the square.
Newburyport
Sitting along the Merrimack River, Newburyport is a town that is rich in waterfronts, also possessing a small Atlantic coastline. Since it has a coastal area, Newburyport is a popular tourist destination, many of whom come to visit the ocean beaches, but stay for the city's lively downtown area. It is very walkable, with bike paths and several boardwalks, including one along the beach and another along the riverfront. It is also an attractive city, with many preserved historic buildings lining the streets and unique storefronts to experience.
Market Square in the Historic District is Newburyport's town square, and is known for its gorgeous Federalist architecture, which is more concentrated here than in most of the US. Market Square sits on the Merrimack River, offering beautiful views, especially from Waterfront Promenade Park. Events such as the Newburyport Holiday Craft Fair are held there annually, and the square holds weekly events as well, like the Newburyport Farmers Market. Around the square, you will also find several acclaimed restaurants, including local legend The Grog, and the breakfast classic Abraham's Bagels.
Amherst
In western Massachusetts, near the Connecticut River, is the small city of Amherst, with a population of around forty thousand people. It is a college town, with three higher education establishments located there, and like Concord, is known for its connection to American literature. It was home to several famous writers like Emily Dickinson and Robert Frost. Therefore, it makes sense that the town has a thriving art scene.
Near the town square, which is called the Amherst Town Common, you will find a few points of interest relating to art. These include the Amherst Cinema, which screens independent films, the Mead Art Museum, which reopens to show all new installations in August 2025, and the Beneski Museum of Natural History, which has both art exhibits as well as fossils and interactive science displays. The latter two attractions also have free admission!
Cohasset
A very scenic coastal city with stunning rocky beaches, Cohasset is a popular summer tourist destination, but year-round, it only has about eight thousand residents. It is known as a hidden gem because it is a small town on the spot where the Boston Harbor meets Massachusetts Bay. It has a couple of charming small public beaches, namely Sandy Beach and Black Rock Beach, both of which are popular with locals and tourists alike. Cohasset is renowned for its stereotypical New England historic feel, complete with a town square called Cohasset Common.
The area around Cohasset Common has a seaside village feel to it, and like a few other towns on this list, it is also a hotspot for the arts. It has a few popular artsy attractions like The Music Circus, a quirky live music venue showing both popular and yet unknown acts, and South Shore Art Gallery, a locally owned non-profit that offers art classes for both adults and children. For a little treat, visit the highly-rated cafe, Seabird Coffee & Co.
Brookfield
In central Massachusetts is the friendly and relaxing small town of Brookfield. Like many towns in the state, it was incorporated in the early 1700's and maintains a historic and rural feel, but it also has a quaint, charming downtown area. Around the Brookfield Common Historic District, which is the quintessential "village green" area that is unique to older European-influenced towns like this one, you will find the things that would be expected in a traditional style town square, like a church, a library, and the town hall.
While Brookfield is quite rural in general, there are several attractions, mostly outdoors, which you can enjoy while in the town. White's Landing, a historic landmark located at a boat dock on the Quaboag River. They offer kayak and canoe tours of the river and work to preserve its natural landscapes while keeping it a safe tourist attraction. The river stems from another poular boating and fishing spot called the Quaboag Pond, which is quite big as far as ponds go at over five hundred acres. Accompanying the pond is cwhich is slightly smaller at three hundred acres, but is known for its clear water and warm temperatures.
Salem
A unique coastal town with a long and somewhat dark past, known for its infamous witch trials which took place in the late 1600's is the town of Salem. It has, in modern years, become a tourist attraction for its speckled history, but it has much more to offer than just that. In addition to the beautiful rocky beaches and stunning Colonial architecture, it has a fun and interesting downtown with endless things to do.
Salem's Town House Square is centered around the Old Town Hall, and is also known as Derby Square, which is a collection of lively shops and restaurants. This area is home to many regularly scheduled events like the Salem Jazz & Soul Summer Series, the Salem Flea and Salvage Market, and the Salem Farmers Market. The entire Town House Square area is notable to the city's literary, maritime and witchcraft history with multiple landmarks and attractions related to those topics.
It is hard to narrow down just a few places to visit in Salem, but a few which tie into the previous sentence that are near Derby Square include the Gallows Hill Museum and Theatre, a live entertainment venue which hosts plays and other live shows in an interactive setting, The Peabody Essex Museum, an esteemed museum displaying regional art, and the New England Pirate Museum, which addresses the darker side of the maritime culture in this region.
Templeton
Incorporated in the 1760's, Templeton is another old town in the central part of Massachusetts, known for its old buildings and pretty downtown area, centered around the Templeton Town Common. The town is small and quite rural, much like Brookfield, but there are a few things to enjoy around the Templeton Common Historic District, including the highly-rated KRO's on the Common restaurant, known for its highly satisfying breakfast meals, and Deer Creek Farm Bagels and Breads, an independently owned bakery producing high quality goods daily.
Most attractions in Templeton are outdoors, and the town common itself is in a charming and quiet wooded area. Just outside of town, you will find Lake Dennison State Recreation Area, which offers a beach for swimming, campsites, and over fifty miles of mountain biking trails. Also nearby is Dunn State Park, a popular destination for hiking.
Sturbridge
Near the Quinebaug River, the small town of Sturbridge is a true glimpse into Old World New England. Its Old Sturbridge Village is a living museum that shows visitors what it was like in the late 1700's and early 1800's, back when the town was a mining village. The Sturbridge Town Common serves as the town square, with a lovely green space, a library, and several cute local businesses around it along Main Street.
The popular Sturbridge Farmers Market takes place on the Town Common weekly, with plenty of local vendors. Another interesting place right off the green is the Publick House Historic Inn, a functional hotel which has been preserved in its original form, built in 1771. On site, it has many rooms in three different houses, as well as a tavern and restaurant onsite, and is a perfect place for visitors to Sturbridge to stay in order to get the full, old New England experience.
Final Thoughts
If you are looking to encounter the heart and soul of New England, complete with European-style town squares surrounded by rich history, breathtaking coastal landscapes, and lively downtowns, Massachusetts is perfect for you. From the weird side of Salem, to the Revolutionary War background of Concord, the state is full of towns with much to learn. If you prefer to enjoy a charming green space and a cool farmers' market to buy some local wares, the town squares in Dedham or Newburyport might be the ideal places. No matter what you want out of your trip to a new town, Massachusetts will have it for you!
