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12 Charming Labor Day Escapes for 2017

There's no place like Massachusetts to enjoy warm, hidden Labor Day gems. We've got you covered for the most beautiful cultural cities, each within a three-hour drive or train ride from Boston. Instead of blending in at Martha's Vineyard or Cape Cod, stand out with the world's largest Norman Rockwell art collection, an Emily Dickinson museum, a rare Trappist brewery, and more!

1. Great Barrington

Photo Source: Sarah_Ackerman/Flickr

Making the map first as the quaintest Berkshire redoubt is a 2012 Smithsonian magazine top 20 town. This mountainous area is American perfection, offering several places on Railroad Street for foodies. It is complete with Colonial properties for history buffs, as well. Soak up a folk music vibe at the Guthrie Center.

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2. Stockbridge 

Photo Source: Ethan Prater/Flickr

With only 2,000 regular residents, here you'll find the Norman Rockwell Museum's oldest art collection. Close to New York's border, you'll be able to take in the paintings of small town life. Boston will feel like it's quite a distance away.

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3. Amherst

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Student or not, you're free to check out this home to 40,000. From college bars downtown to the one and only Emily Dickinson's Museum, it has notable attractions for all ages. Make sure to visit the Yiddish Book Center and Eric Carle Museum of Picture Book Art.

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4. Spencer  


Photo Source: Bill Ilot/Flickr

North of the Turnpike, this town feels more remote than its 1 hour distance west of Boston. Still, its diners are warm and make you feel welcome. Nowhere else will you find a Trappist brewery in the West. Just off State Highway 31 at the St. Joseph's monastery, it even has a gift shop!

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5. Harvard


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An hour's drive from the famous university is another quaint town of about 6,500 residents. They are nontraditional with Shakers, Transcendentalists and communes. The Fruitlands is the oldest Shaker museum. There's one for Native American artifacts. To see communal living you are welcome to explore a mid-19th-century farmhouse experiment.

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6. Concord


Photo Source: Pablo Sanchez/Flickr

With 18,000 people and lots of Revolutionary War reminders, this gorgeous downtown area is rich with literary pedigree. At the Minute Man National Historic Park you can travel back to April 1775. The cemeteries are still home to Ralph Waldo Emerson, Henry David Thoreau, Louisa May Alcott, and Nathaniel Hawthorne.

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7. Lexington

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Also in April 1775 was the American Revolution in the town of over 31,000 people. To see the nation's oldest war monument, you have to visit. Battle Green commemorates the Battle of Lexington, and the Buckman and Munroe museums are dedicated to the conflict.

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8. Nahant


Photo Source: RachelC.Photography/Flickr

Barely connected to the mainland is this 1 square mile municipality near Lynn. With 3,500 people you will enjoy the isolated beaches and bunkers from the Cold War and WWII. Only a half hour drive!

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9. Salem


Photo Source: Madeleine Deaton/Flickr

Any wicked witches of the East reading? Take a break from the 1690s style witch trial hysteria and visit Salem's famous Peabody Essex Museum 45 minutes from Boston. You'll find Asian art, American maritime trading, and a Puritan replica known as Pioneer Village. Population: 40,000.

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10. Newburyport 

Photo Source: Beckwith-Zink/Flickr

Accessible by car or commuter rail, you can be there in just an hour. This coastal town has 18,000 people and enjoyable public waterside space. Make sure to see the Federal-style homes on High Street. Before you leave, souvenir shop on State Street.

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11. Marblehead


Photo Source: Ryan Harvey/Flickr

This goes out to all the kayaking and sailing souls out there. With 22,000 people an hour north of Boston, you'll find the famous yachting community (also known as the probable birthplace of the American Navy). A resident once used what many consider the first fighting vessel in the Revolutionary War. However, he launched his ship from Beverly, Massachusetts' honorable harbor.

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12. Rockport


Last but certainly not least, if you're looking for a quintessential New England seaside town, this is it. Also an hour north of Boston, 7,000 people enjoy lobster fishermen, beaches, wildlife, and laid back energy. Let us know in a comment down below where you plan to end up for the holiday, and remember to enter our Lady Gaga giveaway!

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 12 quaint Boston-area towns to visit right now [Curbed Boston]


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  1. KC on

    Classy :D