Carolyn Kruse

Carolyn Kruse

Carolyn Kruse

Where to find Massachusetts’ best downtowns? Right here!

Small towns are said to be the backbone of America. And our downtowns are where small business and community engagement thrive. The town center is the pulse of the people and pride of the neighborhood. Only In Your State recently released a list of it’s “cutest town squares in Massachusetts.” I’m sharing and adding to it. Take a look at these 8 Massachusetts small towns that have the BEST downtowns.

From the North Shore, to the South Shore, you will find some beautiful coastal communities. From the rolling hills and picturesque valleys Western Massachusetts to the tip of scenic Cape Cod, delightful downtowns decorate the state with charm. All these areas are covered in this lovely list of 8 Massachusetts small towns with the best downtowns.

The Beauty of Downtowns

What makes a downtown is the pride small businesses take in maintaining a sense of small town charm. The streets are lined with privately owned boutiques, cafes, shops, bars and restaurants. It’s what this country was built on. Downtowns provide a place for neighbors to come together. The local markets and green space common areas are the places we can easily walk to or park in. And that also helps to make a downtown flourish.

According to, “Successful downtowns have beautiful gathering places such as a public square with tables and chairs, plants, and perhaps even a water fountain. These gathering places make people want to stay in the downtown for an extended period of time. And they help to get people to form an attachment to a place.” Think of our  downtowns as living, breathing spaces that are the heart and soul of community.

  • 1. Provincetown

    Downtown Provincetown is a marvel. Commercial Street is filled with locally owned shops, restaurants, bars, hotels and community spaces. There is no better people watching on the planet than in Provincetown. It’s a must-see destination. And the fact that you can ferry in is fabulous! There are plenty of designated parking areas. As you walk around you get a sense that everyone knows each other, with the exception of tourists, of course. It’s a tight, artsy, beautiful community. Be sure to visit the historic MacMillan Wharf, or stroll along the beach. Take in an art gallery. Buy some penny candy (Ok, dollars candy), see a show. It’s all right there in downtown P-town.

    There's something special about these cooler nights, clear skies, and busy streets that just makes us stop in our tracks...

    Posted by Provincetown on Monday, September 18, 2023


  • 2. Rockport


    About 40 miles north of Boston is the the quaint and historic town of Rockport. It really is charming. The downtown area is mostly found on Main Street and Bearskin Neck. It’s an art colony that is stocked with shops, restaurants and galleries. And to this it’s all set right there on the harbor with some breathtaking sunsets.

    Rockport USA

    Visit Rockport for our miles of lovely beaches, boulder-strewn paths through woods and glades, and that uncommonly magical light that has inspired painters since Winslow Homer. In an hour's pleasant drive north of Boston, you can enjoy a romantic getaway, exquisite dining and a unique shopping experience year round.

  • 3. Concord

    No other downtown quite captures the essence of colonial New England than the picturesque town of Concord. It’s exemplifies our history. Explore Minute Man National Historic State Park. See Louisa May Alcott’s Orchard House. And Walden Pond is close by. There’s plenty of allure in Concord with lovely little shops and restaurants. You’ll feel like you’ve gone back in time, here.

    Concord, Massachusetts - Scenic Shopping

    Experience shopping in beautiful and historic Concord, Massachusetts.


  • 4. Stockbridge

    A town so full of charm, it was an inspiration for famous works of art! Norman Rockwell’s “Stockbridge Main Street at Christmas” was created because he was so enthralled with the tiny town of Stockbridge, Massachusetts. Saunter down Main Street, take a breath of fresh air and take in the charm of the village. Galleries, cafes and sweet boutiques line the streets. It’s a beautiful place. It’s also where you will find the Norman Rockwell Museum and the famous Red Lion Inn.

    Tickets on Sale Now for Stockbridge Main Street at Christmas.Rediscover the joys of the holidays in Stockbridge, MA....

    Posted by Visit Stockbridge Massachusetts on Friday, September 8, 2023


  • 5. Scituate

    I added to Only in Your State‘s list with this sweet, scenic, seaside town. If you’ve even been to downtown Scituate, you know it’s a special place. Downtown is right there on the harbor and is host to many great restaurants, cafes and shops. Also known as “the Irish Riviera,” because so many of Boston’s Irish immigrants and descendants have moved here to enjoy a quieter life near the ocean.  It has a wonderful town center and seaside village with plenty of eating and shopping establishments. Plus, waterfront activities, entertainment venues, art galleries, live street performers and artists, personal and professional services and more. Scituate was voted It was voted as he 2015 Best Town Center, South by Boston Magazine

    Scituate, Massachusetts: a Great Alternative to Cape Cod Travel

    Scituate, Massachusetts features a cute downtown, splendid harbor and ocean views, beaches, and restaurants with seafood.

  • 6. Amherst

    In the Berkshire County town of Amherst the local shopping is phenomenal. Local book shops, record stores, a vintage store, instrument shop and a great variety of places to see and things to do. There is no shortage of culture in downtown Amherst. From museums to cinema, galleries and culinary experiences, there is something for everyone. It’s filled with old-time New England charm.

  • 7. Falmouth

    Only in Your State raves that Main Street Falmouth “covers a long stretch where you will find a bookstore, clothing boutiques, gift and home decor shops, ice cream shops, and several bars and restaurants.” You’ll find so much Cape charm here. From the quaint bed and breakfasts to beautiful boutique shops and that salty sweet sea air to breathe! There are beautiful views of Falmouth Harbor right there in downtown, too.

    Falmouth, Cape Cod, Massachusetts - Scenic Shopping

    Visit downtown Falmouth with its unique shops on busy Main Street, not far from pretty harbors and beaches.


  • 8. Great Barrington

    Plenty of curbside appeal to soak in here, in downtown Great Barrington. It’s a cozy brick town alive with culture. And it’s another beautiful Berkshires town with historic flare. Farm-to-table restaurants, entertainment venues, boutiques, cafes and more bring locals into the center. Music and art are alive in Great Barrington. The downtown Cultural District offers so much!  It really is great!

    Great Barrington, Massachusetts - Downtown Upstairs

    The largest town in the Southern Berkshires, Great Barrington is a destination in itself with its ample natural beauty and small town charm. Although still a fairly well-kept secret, it has been growing in popularity in recent years thanks to an influx of unique and trendy businesses, drawing in you

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