13 Towns In Massachusetts With The Best, Most Lively Main Streets
×
Sophia
Author
Before supermarkets and sprawling malls, a town’s main street was the center of community life and business. Massachusetts is lucky to still have plenty of bustling, beautiful main streets that ooze old-fashioned charm. Check out these main streets across the state that are packed with places to shop, eat and people-watch.
Stockbridge inspired the classic paintings and illustrations of Norman Rockwell so, of course, it's going to have one of the most charming main streets in the state. Browse the shops, stop by the historic Red Lion Inn, and grab a tasty meal at Once Upon A Table.
This is a lively and happening main street that is filled with plenty of shopping and places to eat. Catch a show at the Iron Horse Music Hall just off the main drag, and then head to Osaka for tasty hibachi and sushi creations.
Advertisement
Main Street in Hyannis is the perfect mix of quaint shops, delicious places to eat and great proximity to natural beauty. There's a large park right in the middle of Main Street, including a path set into the street that will lead you straight to the harbor in a matter of minutes. Stop by Common Ground Cafe for a whimsical and cozy dining experience, and be sure to stock up on sweets at Kandy Korner.
Advertisement
Known for being one of the liveliest towns on the Cape, Provincetown has an equally colorful and fun main street. The nightlife opportunities here are almost endless, and there are plenty of nice places to get cheap or fancy seafood. Don't forget to check out the art galleries scattered all around.
Great Barrington has one of the most popular main streets in the Berkshires, and it's a wonderful spot to do some shopping and indulge in a hot drink. Stop by Fuel Coffee Shop to recharge, browse fantastical playthings at Tom's Toys, and when you're done on Main Street, head over to Railroad Street (pictured) for even more cool shops to explore.
Main Street in Historic Deerfield is unlike the other the other central avenues on this list, but it's a must-visit destination nonetheless. Here you'll find countless historic homes, shady trees and an atmosphere that feels like stepping back in time.
Related Stories
You'll Never Look At Donuts The Same Way After Trying Kane's Donuts In Massachusetts
I Discovered My Family Roots At The Village Pancake House In Rowley, Massachusetts
7 Waterfront Retreats In Massachusetts That Are Perfect For Warm Weather Adventures
Main Street in Lee is loaded with cool shops, great dining spots and places to watch the crowd roll by. Check out the Starving Artist Creperie and Cafe for a sweet snack, and then head to Moe's Tavern for an evening drink.
Falmouth has a quintessentially Cape Cod main street area. There are lots of little shops where you can peruse nautical knick-knacks, jewelry and local crafts. It's also a great place to simply take a stroll on a warm summer day.
Advertisement
North Adams is way out in the Berkshires, and its main street packs a ton of stuff to do into a relatively small space. Stop by Jack's Hot Dog Stand (it's actually a brick-and-mortar shop) for a delicious bite to eat, peer into the quirky ships, and then head to Mass MoCA for a fun dose of culture and art.
Edgartown in Martha's Vineyard is a beloved island hotspot, and the main street here is filled with the most charming businesses and dining opportunities. Stop by Edgartown Books to find your next favorite beach read, and indulge in a delicious dinner at Alchemy.
Most of Nantucket feels like a charming main street, so you really can't go wrong with your wanderings. Main Street winds all the way down to the sea through the Nantucket Historic District, so you'll be surrounded by beauty and history on all sides.
Concord is a historic Massachusetts community that also happens to be incredibly picturesque. Its main street is a great place to take in the beauty of autumn foliage, or treat yourself to a decadent snack at Patti's Homemade Whoopie Pies.
Lowell isn't exactly a sleepy hamlet, but it has a downtown that combines the best of old-fashioned charm with plenty of great places to shop and eat. The area is filled with red brick buildings, fun sidewalk cafes, and cool boutiques.
For more Massachusetts small town fun, check out these 11 teeny tiny towns that are so small, you might have never heard of them.
OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.