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The Most Charming Small Towns in New England

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You want to look for a better America for yourself in retirement. Finding a small town can be just right for many retirees who want to slow down and take things easy. The Boston Globe has rounded up a list of the best small towns in New England, including ten that just might be the right place for you. Here they are:

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A town in Massachusetts made famous by Norman Rockwell is the most charming small town in America, according to Big 7 Travel.

Stockbridge in the Berkshires ranked No. 1 on the travel website’s list of 50 most charming small towns in America, released earlier this month. Big 7 Travel called it “the ideal New England small town” due to its charming square, historic inns, preserved homes, community events, and local eateries.

“Stockbridge looks like something out of a Norman Rockwell painting, and that’s because it is!” Big 7 Travel wrote. “This cosy New England town was made famous by his portrayal of the city during Christmas.”

Woodstock, Vermont, snagged the No. 2 spot on the list because “you can enjoy delicious farm-to-table meals, endless scenic trails, and then experience its rural heritage without ever getting on a highway,” Big 7 Travel wrote.

A total of 10 New England small towns made the list. The towns had to have a maximum population of 50,000 and “hold a unique quality,” according to Big 7 Travel.

Here are the New England towns that made the cut and how they ranked:

  1. Stockbridge, Mass.
  2. Woodstock, Vermont
  3. Sugar Hill, N.H.
  4. Meredith, N.H.
  5. Mystic, Conn.
  6. Stowe, Vermont
  7. Nantucket, Mass.
  8. Bennington, Vermont
  9. Great Barrington, Mass.
  10. Montpelier, Vermont

View the entire list of the 50 most charming small towns in America.

Remember to consider the benefits of small-town living when you’re choosing where to retire.

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E.J. Smith - Your Survival Guy

E.J. Smith is Founder of YourSurvivalGuy.com, Managing Director at Richard C. Young & Co., Ltd., a Managing Editor of Richardcyoung.com, and Editor-in-Chief of Youngresearch.com. His focus at all times is on preparing clients and readers for “Times Like These.” E.J. graduated from Babson College in Wellesley, Massachusetts, with a B.S. in finance and investments. In 1995, E.J. began his investment career at Fidelity Investments in Boston before joining Richard C. Young & Co., Ltd. in 1998. E.J. has trained at Sig Sauer Academy in Epping, NH. His first drum set was a 5-piece Slingerland with Zildjians. He grew-up worshiping Neil Peart (RIP) of the band Rush, and loves the song Tom Sawyer—the name of his family’s boat, a Grady-White Canyon 306. He grew up in Mattapoisett, MA, an idyllic small town on the water near Cape Cod. He spends time in Newport, RI and Bartlett, NH—both as far away from Wall Street as one could mentally get. The Newport office is on a quiet, tree lined street not far from the harbor and the log cabin in Bartlett, NH, the “Live Free or Die” state, sits on the edge of the White Mountain National Forest. He enjoys spending time in Key West (RIP JB) and Paris. Please get in touch with E.J. at ejsmith@yoursurvivalguy.com To sign up for my free monthly Survive & Thrive letter, click here.
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