Massachusetts is certainly not lacking in charm. You can pretty much spot a picturesque white steeple, historic building, or gorgeous ocean sunset anywhere you go. These towns just kick it up a notch. Check these small towns out for your daily dose of nostalgia and classic New England beauty.
Population 1.9k. No list of small towns in Massachusetts (or America, for that matter) would be complete without Stockbridge. This is the town Norman Rockwell used as a model. If that doesn't convince you that this place is loaded with charm, go visit for yourself. Book a room at The Red Lion Inn (built in 1773) and grab an old-fashioned meal at the Elm Street Market lunch counter.
Population 5k. Man, this place is pretty. The landscape of Hadley is largely open-field farming, which is so unique in Massachusetts as that kind of farming largely ended in the 18th century. The "Cultural Landscape of Hadley, Massachusetts" is actually on the World Monuments Fund's watchlist for endangered sites. Go take in the beauty and charm of Hadley while you still can!
Population 7.5k. Cape Cod isn't the only place to find charming seaside spots in Massachusetts. Stroll around the Bearskin Neck area and don't miss The Paper House, a real house constructed out of actual newspaper.
So the town of Westford might be a slightly larger small town with its population of 22k, but this place definitely has that small town feel. Spend some time on the slopes at the local Nashoba Valley ski resort and check out the Westford Academy's bell tower – that bell was made by Paul Revere!
This town is dripping with quaintness. Have a stroll down State Street and enjoy an ice cream in Market Square. If antiquing is your game (or you just love funky doodads) you need to visit Oldie's Marketplace. It's a giant barn absolutely crammed with all sorts of oddities and treasures.
Forget being a small town – Rowe is more like a micro-town. With a population of 393, this sleepy spot is perfect for getting away from the bustle of urban life. Splash around in Pelham Lake and enjoy the classic New England scenery. A great place for hiking, fishing, hunting, canoeing and kayaking.
7. Oak Bluffs
Population 3.7k. Nestled on northeastern shore of Martha’s Vineyard, this picturesque small town features an incredible seaside park (Ocean Park) and a cluster of fairytale-style "gingerbread houses." Be sure have a spin on the Flying Horses Carousel, which is the oldest in the nation. Fun for junior gallopers and veteran jockeys alike.
Provincetown isn't exactly a hidden gem. This art colony's population can swell to over 60k in the summer, but its year-round population is actually only 2.9k! Come here for the shops, galleries, and LGBT-friendly celebrations. Grab lunch at The Lobster Pot and soak up some sunshine at Race Point Beach.
Population 5k. This sweet Massachusetts town is the site of Tanglewood, summer home of the Boston Symphony Orchestra. A visit to Lenox would not be complete without dropping by to marvel at the estate. Though if you'd prefer to just spend the day riding around town in a horse-drawn carriage, I totally get that.
This town was the site of The Battle of Lexington and Concord, the first battle of the American Revolution. Home to Minuteman National Historic Park (prime picnic real estate) and Walden Pond (Henry David Thoreau thought this was a pretty cool place), Concord is brimming with old-fashioned charm.
Whether you’re looking for a scenic drive or an extended stay in a charming locale, these spots have you covered. What are your favorite beautiful small towns in Massachusetts?