Massachusetts Town Named ‘Most Charming’ and I Say it’s the People

Massachusetts is full of beautiful small towns worth visiting. Whether it's the folks in Provincetown who are known to greet you with nothing but open arms or the hip, college feel of Northampton, Massachusetts has plenty of small towns that you can make a day, weekend, or week-long trip out of and will want to return to many times in the future. They're just that good.

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One small Massachusetts town that made Thrillist's must-visit list and named the most charming in the Baystate is Great Barrington. With a population of a little more than 7,000 Great Barrington is perfect to visit for a weekend getaway. Let's see the site's review of this beautiful small town in the Berkshires.

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.

 

As someone who has worked in Great Barrington for almost 20 years, I'm in agreement with Thrillist's recommendation of Great Barrington but to me, there's another aspect to the town that I find attractive and that is the people.

I didn't grow up in Great Barrington but when I started working in the town I noticed right away that there was something different about the residents here. They seemed more friendly, happy to be here and always go out of their way to greet you. I have interviewed many Great Barrington folks on the radio over the years and the majority of those folks were very thankful and showed gratitude toward me.

You see the friendliness out in the community as well. When I'm walking down the street or doing a live broadcast the community in general just feels welcoming and I'm always greeted with smiles and happy folks. There's nothing like it. Plus when our station runs our summer concerts on Tuesday evenings, the attendees regularly come up to me and say how much they love the concerts or it's a wonderful thing our station offers to the community. No matter what time of year, Great Barrington is always a breath of fresh air.

If you haven't visited Great Barrington but want to visit soon. Come check out the town this December as the Southern Berkshire Chamber of Commerce's Holiday, Shop, Sip & Stroll event is a wonderful experience that will put you in the holiday spirit. From hay rides along Railroad and Main Streets from Santa, holiday music, hot cocoa, Christmas Carols, winter bonfires, live music, happy faces, and fireworks...yes fireworks in the winter. The Holiday, Shop, Sip, and Stroll event is a can't-miss experience. The stroll takes place on December 14.