7 Small Towns In Massachusetts That Are Full Of Charm And Perfect For A Weekend Escape

Massachusetts is filled with small towns, but there are some that make for absolutely perfect weekend trip destinations. Here are our picks for a few of the most picturesque, interesting, and worthwhile small-town weekend getaways in Massachusetts.

What are your favorite small-town weekend getaways in Massachusetts? Have you been to our picks? Share your thoughts and experiences with us in the comments section below!

Address: Concord, MA, USA
Address: Stockbridge, MA, USA
Address: Edgartown, MA, USA
Address: Hadley, MA, USA
Address: Newburyport, MA, USA
Address: Chatham, MA, USA
Address: Rockport, MA, USA

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The OIYS Visitor Center

small town weekend getaways in Massachusetts

September 20, 2022

What’s the most historic small town to explore in Massachusetts?

Looking for a haunting historic weekend in Massachusetts? Salem may be known as the most haunted small town in Massachusetts, but don’t let that keep you away. In the Northeast, pretty much any small town you visit is going to be incredibly old and historic, full of lore and legends. Today, Salem is working hard to shrug off centuries of baggage and superstition, embracing its history and gravitas with its vibrant and well-preserved downtown district. And they’ve been successful, too; Salem is one of the larger towns on our list, as it’s become a place residents are proud to call home. Visit and you’ll see why!

What are the most charming small town in Massachusetts?

The above small-town weekend getaways in Massachusetts are all destinations sure to sweep you off your feet with their charms, but really, our state is full of so many delightful little locales to visit! Rockport, Massachusetts, is a place we love because it really is *peak* New England vibes. For starters, there is its location: set on the rocky coast, Rockport is a typical New England town that exudes charm, complete with jagged shorelines, fisherman’s wharfs (including Bradley Wharf, an iconic red building in MA!), gorgeous lighthouses (Thacher Island is home to *two* beautiful beacons!) and, of course, stunning Atlantic Ocean views. In addition, Rockport is home to, in our very humble opinion, some of the best seafood shacks in the Northeast. Roy Moore Lobster Co. is one of our all-time favorite lobster shacks; this local establishment has been open since 1918 and is known for serving some of the absolute BEST fresh lobster in New England! This quaint seafood shack offers fresh lobster in the rough that’s cooked straight from the sea. You can’t get a fresher meal anywhere else. Be aware, however, that it’s only open seasonally (spring through mid-fall), so definitely plan your getaway to this charming Massachusetts town around that (trust us — it’s worth it!).

Address: Concord, MA, USA
Address: Stockbridge, MA, USA
Address: Edgartown, MA, USA
Address: Hadley, MA, USA
Address: Newburyport, MA, USA
Address: Chatham, MA, USA
Address: Rockport, MA, USA

OnlyInYourState may earn compensation through affiliate links in this article.