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9 Amazing Small Towns to Retire In

May 20, 2022 · Retirement Life
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Pittsfield, Mass.

New England is known for its expensive lifestyle, but Pittsfield, which is located in the western part of Massachusetts, comes with a bit more affordability, and more reasonable prices than Boston and Cambridge.

Housing is also affordable, as the median home value in the city is $173,200, in comparison with $407,400 for any area in Massachusetts and $592,300 for Boston proper. There are so many things to enjoy in this city!

From excellent places to camp, fish, hike, and go skiing, to musical performances at the Tanglewood Music Center, and the summer home of the Boston Symphony Orchestra. If you’re an art lover, your schedule will be constantly busy, as you’ll be occupied with the world-class art at the Clark Art Institute in Williamstown or the Massachusetts Museum of Contemporary Art.

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53 comments on “9 Amazing Small Towns to Retire In”

  1. Gloria Vazquez says:
    February 27, 2023 at 3:47 pm

    Yes, everyone that works should have benefits for their retirement.

    Reply
  2. PSFraulino says:
    June 11, 2023 at 5:28 pm

    Regarding article by Dorothy ,”9 Amazing Small Towns to Retire In” Middletown, Connecticut is first. I grew up in Middletown and visit once in a while. Restaurants are a too many thing on Main Street,etc. The ability to purchase newspapers for local news is gone. Unless a college-related bookstore has changed its mind. It is no longer a Barnes/Noble corporate bookstore. Central News, a longtime outlet is long gone and is replaced by a sandwich shop. A lunch place called Ford News has no newspapers despite its name and serves meals like a diner till midafternoon . Also on Main Street north of that location is another diner. Both have been main stays on Main Street long before these new food palaces arrived on the scene and seem to give Middletown its new reputation. As for Wesleyan Univ., one must live downtown to only walk to campus for amenities. Middletown Area Transit buses operate Mon-Sat 6am-6pm only. I would like my former city to be like other New England towns with a operating main street. Grocery stores have left downtown also. Drug stores also are gone from downtown

    Reply
  3. Paul says:
    February 14, 2024 at 2:21 pm

    You are out of your minds! Recommending ice boxes like Montana, Minnesota, New England states, etc. to us old geezers with aches and pains and no desire to tread on snow and ice is a total non-starter.

    Reply
  4. Kim says:
    February 14, 2024 at 4:21 pm

    I have a strong feeling that these candidates for “best” are bought and paid for. Older folk with their chronic issues typically hate the cold.

    Reply
  5. Ken says:
    February 14, 2024 at 10:12 pm

    I live in Vermont and would not consider Burlington a small town. It is a nice place but is also the largest city in the state.

    Reply
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