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  1. Chester is a town in Middlesex County, Connecticut, United States. The town is part of the Lower Connecticut River Valley Planning Region. The population was 3,749 at the 2020 census. [2] The town center is defined by the U.S. Census Bureau as a census-designated place (CDP).

  2. Right between Boston and NYC on the rolling, hilly banks of the Connecticut River, Chester is an artsy community that takes pride in its rich history (it was settled in 1692!) and lush farm-filled landscape surrounding the town.

    • Enjoy The Charming Downtown. One of the biggest draws is most definitely the charming downtown, which is lined with independent shops and restaurants housed in colorful buildings.
    • Get An Ice Cream At Honeycone. Along Main Street, you’ll also find the adorable Honeycone ice cream shop, and this is a must during your visit! They make delicious, craft homemade ice cream here, and they introduce amazing seasonal flavors monthly.
    • Grab A Pint A Little House Brewing. For such a small town, it come as a surprise that Chester has its own brewery! And, it’s actually really great. My husband is really into beers, and he absolutely loved it here.
    • Book A Table At The Brushmill By The Waterfall. One of the most scenic restaurants in Chester is the Brushmill By The Waterfall, and just your walk from the parking lot to the restaurant is going to feel special because you have to go across the cute little covered bridge.
  3. Often described as quaint and unique, Chester has a picturesque Main Street with interesting architecture, elegant shops, art galleries, superior restaurants, and the world renowned Goodspeed Opera House’s local Norma Terris Theatre.

  4. Nov 18, 2020 · Chester, Connecticut is one of the most beautiful tiny towns in the state, not to mention has serious industrial roots in milling and shipbuilding. If you want to explore a bustling cultural Mecca on a miniature scale, then we have the town for you.

    • Chester, Connecticut, United States of America1
    • Chester, Connecticut, United States of America2
    • Chester, Connecticut, United States of America3
    • Chester, Connecticut, United States of America4
    • Chester, Connecticut, United States of America5
  5. 6 days ago · Visit Chester CT. Discover Chester Connecticut. Friday, June 21st. 5:00 to 8:00 p.m. Midsummer Night Stroll. on Make Music Day. Join us for a summer solstice celebration of live music! From 5:00 to 8:00 p.m. local musicians will be playing live throughout the village.

  6. Chester, CT: Chester Historical Society, 1976. Chester, in Middlesex County, is located in the lower Connecticut River Valley in southeastern Connecticut. Large portions of Cockaponset State Forest cover its northern and western boundaries.

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