The Smithsonian called Great Barrington the best small town in America, and we’re inclined to agree. There’s something indescribably comfortable yet energetic about this small mountain town. Great Barrington is a quirky, beautiful and exciting place to visit. You'll leave with more memories than you can carry home, and a newfound appreciation for the charms of Western Massachusetts.
Read on to learn why Great Barrington just might be one of the most unique places in the world.
Great Barrington is so unique because it combines the excitement and variety of the big city with the slow-paced charm and natural setting of a classic New England small town.
It's home to less than 10,000 residents, but is a nexus of culture, art and shopping in the Berkshires.
Just how unique is this place? Well, for starters, it has its own currency. BerkShares bills are accepted at over 400 local businesses, ranging from grocery stores to clothing shops.
Head to Railroad Street, which looks postcard-perfect. It's where many popular eateries and businesses are located.
Stroll along Main Street, where the blooms of flowering trees are wafted through the air by sweet-smelling, fresh mountain breezes.
Great Barrington was incorporated in 1761, which means that its streets are lined with everything from colonial homes, to massive, old mill buildings.
Entertainment is definitely not lacking here. Tanglewood, Shakespeare & Company, the Norman Rockwell Museum and Jacob’s Pillow Dance Festival are all amazing nearby productions and attractions.
To catch a show in town, try the 101-year-old Mahaiwe Theater. It hosts everything from the New York Metropolitan Opera, to rock shows and lectures.
This town is also unique due to its stunning location in the Taconic Mountains. It's an official Appalachian Trail community, making it ideal for hikers and explorers.
Monument Mountain looms up over the town, dramatic and totally hikeable. Even beginners will love scaling this beautiful peak.
For a great slice of pizza, head to local favorite Baba Louie’s.
Their pies are made from fresh sourdough, and rival those from any artisan pizza shop around.
Great Barrington is devoted to its fresh and local food scene. There are almost daily farmers markets, and plenty of local family farms and co-ops to choose from.
This was also once the home of Alice’s Restaurant, about which Arlo Guthrie wrote the famous song “Alice’s Restaurant Massacree.”
The restaurant was later turned into a cafe, which has since closed.
Great Barrington is also home to one of the country’s few grand castles. Searles Castle was built as a Gilded Age mansion in the style of a French Chateau.
Today, it is used as a boarding school. Attending school there must feel like being a student at Hogwarts.
There's really no reason not to visit this charming mountain town right away.
For another underrated but gorgeous destination in Massachusetts, check out this remarkable hilltop with a breathtaking view.
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