We all like to get out and explore, but sometimes it can be really hard to figure out where to spend our hard-earned free time. There’s nothing like wandering through a charming and scenic small town full of interesting sights and flavors, but which one should you pick?
This road trip is designed to take you through some of Massachusetts’ most delightful small towns without the headache of trying to figure out where to go and how to get there. You can choose to visit all of these towns over a long weekend, or pick just one to really soak up the local flavor. This road trip can be completed in 9.5 hours if you start in Williamstown, or 11.5 hours if you start in Newburyport. However, you’re going to want to budget at least a few hours in each town to really get the intended experience. Click here for the interactive road trip map.
Old whaling mansions, gorgeous brick roads and an air of timelessness. Newburyport offers all that, plus some really amazing spots to grab a bite, drink or incredible view. This North Shore gem is sometimes overlooked in favor of places like Salem of Gloucester, but it's really worth stopping in this charming coastal town for an afternoon. Fuel up on some 25 cent hot dogs at Richdale's, peruse the antiques at Oldie's and then head to the harbor to watch the sunset.
Williamstown doesn't get as much love as the seaside small towns of the coast, or the more well-known communities of the Berkshires. This place deserves way more recognition though, because Williamstown is a ridiculously charming and scenic place to wander and explore. It's home to Williams College, so the sleepy colonial atmosphere of the place is tempered with a vibrant student culture. It's the perfect stop for those looking for a peaceful country escape with enough going to keep you entertained.
No list of picturesque communities would be complete without the quintessential New England small town. This place looks like something out of a Norman Rockwell painting in every season, which means you shouldn't shy away from a visit in the winter weather. Cuddle up to the fire at the Red Lion Inn, and be sure to grab an old-fashioned meal at the Elm Street Market lunch counter.
Hadley is one of the last places in Massachusetts where the agricultural landscape hasn't changed much since the town was founded. Rolling acres of sunflowers, amazing proximity to natural treasures such as the Fort River Birding and Nature Trail (pictured), and a general small town cozy feel makes Hadley the perfect place to stop and take in the beauty of the environment. If you're in the mood for some of the best ice cream around, grab a scoop at Flayvors of Cook Farm.
The town of Sturbridge is best known for its living history museum, Old Sturbridge Village. History buffs will be in absolute heaven wandering around this idyllic colonial town, complete with horse-drawn carriages and period dress. If you're not as interested in the historical, Sturbridge still has plenty to offer.
Eastham is known for being one of the more posh towns on Cape Cod, but there's plenty to do here without shelling out major cash, or even opening your wallet. Visit Coast Guard Beach (pictured) in any season to experience some of the most stunning ocean views on the Cape. Grab a bite to eat at Arnold's Clam Shack, a Cape Cod seafood classic.
Another day, another devastatingly charming South Shore small town. Explore the tiny shops, take in the smell of the sea and feast on fried clams and soft serve ice cream. Scituate gets a fair amount of tourists in the summer, but it really shines in the spring and fall before the crowds settle in. If you do visit in the summer, their Fourth of July celebration is out of this world. Plus, if you feel like deviating a bit from the road trip route, the equally gorgeous towns of Cohasset and Hull are only a quick drive away.
Marblehead has almost 300 surviving colonial-era homes. That's actually the most of any town in the entire country. Add in its picturesque harbor and great downtown, and Marblehead starts to look more and more like a postcard-perfect day trip destination. Check out the Old Town district for an amazing array of colonial homes, galleries, restaurants and boutiques. Don't forget to head to the wharf to pick up some prime seafood right off the boat.
Rockport features the most painted building in America: Motif No. 1., a humble, red fishing shack on the harbor. Even if you're not an artist, it's a must-see spot. Later, head into town for a bite to eat at one of the many amazing seafood restaurants in Rockport, and browse the handcrafted wares at the Stop by the Pewter Shop. They've been churning out incredible metalwork since 1935, so every item is a piece of history.
Looking for more Massachusetts travel inspiration? Check out these 13 legitimately fun and free things you can do in Massachusetts without spending a dime.
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