• Kids Potato Sack Race

    Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States
  • Kids Mini Horse Pull

    Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States

    Time TBD: Afternoon

  • Kids Under 12 Bicycle Raffle: Sunday, August 6

    Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States

    What kid under 12 would not want a chance to win a new bike? Here's a raffle any kid will love! But you must be present to win, so plan to be at the Littleville Fair on Saturday at 6pm for the drawing!

  • Flower Box Winner Announced

    Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States

    Come see who wins!

  • Littleville Fair Car Show

    Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States

    Littleville Fair Car Show September 16, 2023  ::  9am-2pm Gates open @ 9am for Show Cars, 10am for spectators Sponsored by L.P. Adams

  • Easter Egg Hunt

    Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States

    The Littleville Fair, the Chester Hill Association, and the Chester Recreation Committee will co-host their annual EASTER EGG HUNT Sunday,  April 13, 2025  @  1 pm Please join us on Sunday, April 13, 2025 for the Littleville Fair, the Chester Hill Association, and the Chester Recreation Committee EASTER EGG HUNT at the Littleville Fairgrounds. The Hunt will

  • Littleville Fair Pancake Breakfast

    Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States

    Sunday, April 27, 2025 ::   7 AM – 1PM @ The Fairgrounds, 15 Kinnebrook Rd, Chester, MA Save the date and plan to join us for the Annual Littleville Fair Pancake

  • Two Classes of Oxen Draws: Friday, August 1

    Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States

    Two classes of oxen draws, 1,600 lbs and 2,000 lbs. This event is free with admission to the fair.

  • Breakfast @ Food Booth: August 2

    Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States

     Join us for breakfast at the Food Booth!