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.

1. Stockbridge
Stockbridge, MA, USA
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Stockbridge is a picturesque rural town with a lot of fun hiding behind its sleepy exterior. It’s famous for inspiring artist Norman Rockwell, and the town’s Main Street looks just like a painting. However, Stockbridge is also home to fantastic nature trails and the unparalleled Berkshire Botanical Garden. Railroad enthusiasts will also want to climb aboard the nearby Berkshire Scenic Railway, which provides scenic trips between Adams and North Adams.
2. Hadley
Hadley, MA, USA
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Nicknamed "The Asparagus Capital of the World," Hadley is so quaint that the "cultural landscape of Hadley, Massachusetts" is actually listed as an official World Monument. The rolling farmland, pretty white buildings, and beauty of the Connecticut River make this town a great option for those looking to escape into nature. Try hiking the Metacomet-Monadnock Trail and bed down at the Old Mill Inn for a comfy night’s rest.
3. Concord
Concord, MA, USA
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Concord is a bustling town with plenty of stately 18th- and 19-century buildings. Drop by Sleepy Hollow Cemetery to check out the graves of literary luminaries like Louisa May Alcott, Nathaniel Hawthorne, Henry David Thoreau, and Ralph Waldo Emerson. You can also head to Walden Pond to see the spot that inspired Thoreau and wander over Old North Bridge in Minuteman National Historic Park. If you want to spend the night, you couldn’t do much better than Concord’s Colonial Inn.

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4. Rockport
Rockport, MA, USA
Getty/Kirby Matthess
Visiting Rockport should be on every coastal explorer’s must-do list. This small town is famed for its old-fashioned downtown drag, known as Bearskin Neck, that’s crammed with ice cream shops, galleries, gift stores, and seafood joints. Don’t miss taking a look at Motif No. 1, an iconic red shack on the water that’s said to be the most painted building in America. Check into the Yankee Clipper Inn to spend the night in a 1929 Art Deco mansion on a cliff over the sea.
5. Newburyport
Newburyport, MA, USA
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You actually don’t have to drive too far from Rockport to find the pretty town of Newburyport, but these towns have totally different flavors. Newburyport is a classic maritime community with a busy waterfront, tons of gourmet restaurants, and plenty of places to shop. You’ll love strolling by the harbor with an ice cream cone or slice of pizza from Abraham’s Bagels and Pizza. And don’t miss the town’s annual Yankee Homecoming event at the end of July!
6. Chatham
Chatham, MA, USA
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Chatham is located on the "elbow" of Cape Cod, making it a convenient base from which to explore the whole Cape. The town itself is beyond charming, with lots of little shops, old-fashioned architecture, and seafood aplenty. Head to Chatham Lighthouse Beach for a peek at a grand old lighthouse and one of the prettiest seashores in the country. For a luxe overnight, check into the Chatham Bars Inn.
7. Edgartown
Edgartown, MA, USA
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You just can’t match the charm and beauty of Martha’s Vineyard and Nantucket, and Edgartown is one of the best island towns in Massachusetts. Located "down island" on the Vineyard, this spot boasts some of the most eclectic and luxurious shopping in the state. You’ll find everything from fine jewelry to hand-blown glass baubles. And of course, the cuisine is world-famous. Head to Right Fork Diner for lobster eggs Benedict in the morning and make reservations at Raw 19 Oyster Bar for dinner. As for accommodation, there’s no such thing as a bad place to stay on the Vineyard.

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!

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small town weekend getaways in Massachusetts

Sarah M. | 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!).

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