Beloved Massachusetts Spot Named 'Most Charming Small Town' In The State

By Logan DeLoye

October 11, 2024

Great Barrington, Massachusetts
Photo: iStockphoto

Small towns are a dime a dozen, but there is one in each state that stands out from the rest to provide the most unique and memorable experience to visitors and tourists alike.

Be it a quaint town square, picturesque park, or quirky presence, something about this Massachusetts town makes it so unforgettable that it landed on a list of the United States' most charming small towns.

If you've been searching for a place to explore, perhaps away from the hustle and bustle of the state's biggest cities and most popular tourist attractions, look no further than this state gem!

According to an updated list compiled by Thrillist, the most charming small town in all of Massachusetts is Great Barrington. This town was named most charming due to its stunning naturescapes and live music!

Here's what Thrillist had to say about the most charming small town in the entire state:

"Let everyone else crowd the Catskills so the largest town in the Southern Berkshires remains a secret as long as possible (except, of course, from the hikers passing through on the Appalachian Trail). History buffs will love a few fun pieces of trivia like the Main Street here was first in the country to have electric lights, Railroad Street is one of the oldest in the US, and, by the town hall, the monument that commemorates the first armed resistance against the British is on the same site as the first slave being freed. Start the morning with coffee (or a lavender latte, if you’re feeling adventurous) and a breakfast sandwich or huevos rancheros at Fuel before antique fair- and gallery-hopping around town (be sure to check Bernay Fine Art off your list). End the afternoon and ease into the evening with a drink and live music by the fireplace at aptly named The Barn. There’s also a historic inn next door, so you don’t have to go too far when you’re ready to call it a night."

For a continued list of the most charming small towns across America check out thrillist.com.

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