5 Small Towns in Massachusetts So Dreamy, You’ll Swear You’ve Seen Them on TV

With the Berkshires, Cape Cod, Nantucket and famous cities like Boston and Salem, Massachusetts isn’t lacking in well known places to visit. And yet, so often when this is the case, there are small towns that are overlooked even when in or near the famous regions. This list is meant to right that wrong, bringing attention to small towns in Massachusetts that are positively dreamy in their beauty. 

1. Chatham

Location: southeastern Cape Cod

Why It’s So Dreamy: This is the town to get all of the experiences you know and love from Cape Cod, but in a way that feels more historic and less manicured, while still being touristy. With well-kept beaches and lighthouses, this place looks like a town out of history with classic New England fishing village style homes, piers, and ramshackle restaurants. The ocean is everything to this town, with seals barking by the docks, boats hauling in daily catches (and often, a group of tourists to tour the coast), and tide pools to (safely and humanely) explore!

2. Stockbridge

Location: Western Massachusetts near the New York border

Why It’s So Dreamy: Forever immortalized by Norman Rockwell (both in paintings and in his choice of home), Stockbridge is a piece of classic New England. Located in the Berkshires (famous for fall foliage and gorgeous forests), the town has historic buildings from the colonial era to the Gilded Age, numerous charming shops and restaurants, galleries, and a dedicated art scene (again, thanks to Rockwell). 

3. Sandwich

Location: On the Upper Cape of Cape Cod

Why It’s So Dreamy: As one of the oldest residential areas on Cape Cod, the town of Sandwich is more than just an odd name. Out of all of the cute, quaint small towns on the Cape, it offers a calmer and more nature-centered option to visit while still providing an endearing downtown area with historic homes and museums (because, when you’re a town founded in 1637, you’ve got quite a bit of colonial history to share). 

4. Deerfield

Location: Northwestern Massachusetts 

Why It’s So Dreamy: It’s perhaps the most ‘historic’ option on this list (and that's saying something), with a dedicated ‘Historic Downtown’ area that is both a living, outdoor museum as well as a national historical landmark. With houses, farms, and other buildings dating back to the 18th and 19th century, few other towns can boast this level of authenticity. But, even beside the historic downtown, Deerfield is walkable and beautiful with a gorgeous surrounding area full of greenery, mountains, and even a butterfly conservatory! 

5. Lenox

Location: Western Massachusetts 

Why It’s So Dreamy: Lenox is similar to Stockbridge in being a bit of quintessential New England with a former famous resident, but it’s slightly less touristy and a bit more upscale. The town has more of a storybook-look to it with manicured parks, historic buildings like the Mount (Edith Wharton’s house, author of famous Gilded Age novels like ‘The Age of Innocence’), antique shops, smaller galleries, and higher-end restaurants. 

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