Chester Vacations, Tourism & Travel Information

Our Take on Chester, Massachusetts

Welcome to Uptake for Chester, Massachusetts. This guide is intended to be your starting point for all of the things to do and places to stay in Chester, Massachusetts. Our recommendations are based on ratings and reviews from across the web. If you are looking for ideas for a family vacation, check out the listing on the left side of the page.

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Chester, Massachusetts Things To Do

  1. Miniature Theater of ChesterChester Town Hall
    Middlefield Street, Chester, MA 01011

    Overview Founded in 1990 by actor, director, and former artistic director of Ireland's Abbey Theater, Vincent Dowling, productions attract ... more on TripAdvisor

  2. Chester Hill Winery47 Lyon Hill Road
    Chester, Massachusetts 01011

    Overview Open from 1 to 5 pm on the weekends from June through December (or by appointment) this winery specializes in Blueberry wines and also offers other vegetables and goods during harvest season. Well ... more on DogFriendly.com

  1. Otis Ridge
  2. Notchview Reservation
  3. Bousquet Ski Area

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