2019 Event Schedule
Events
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Old Country Road Band @ Littleville Fair: Saturday, August 2
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesThis performance is free with admission to the Littleville Fair.
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Kids/Adults Blueberry Pie Eating Contest: Saturday, August 2
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States -
Ed Popielarczyk’s Magic Show & Balloon Sculpting: Saturday, August 2
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesCome prepared to be entertained and amazed!
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Kids Pedal Tractor Pull: Saturday, August 2
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesCome cheer for the kids as they pedal their tractors through the pedal-tractor pull!
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Farm Olympics: Saturday, August 2
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States -
Henry the Juggler
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States -
Women’s Fry Pan Toss: Saturday, August 2
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesWho will be the fry pan tossing champ? Be at the fair on Saturday at 4:00 pm to find out!
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Ed Popielarczyk’s Magic Show & Balloon Sculpting: Saturday, August 2
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesCome prepared to be entertained and amazed!
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Demolition Derby: Saturday, August 2
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesRegistration from 12pm-3pm.
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Petting Zoo & Family Jungle: Friday, August 7
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesYoung boy feeding goats at a petting zoo Our Petting Zoon & Family Jungle are open when the Fair is. Stop by to cuddle a critter or meet at jungle …
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Gates Open & Raising of the Flag Ceremony: Friday, August 7
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesHelp us kick off the 2026 Littleville Fair and say Happy 250th Birthday to the USA!
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Truck Pull Weigh In: Friday, August 7
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesTruck Pull @ Littleville Fair This event is free with admission to the fair.
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Two Classes of Oxen Draws: Friday, August 7
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesTwo classes of oxen draws, 1,600 lbs and 2,000 lbs. This event is free with admission to the fair.
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Bingo in the Dining Hall: Friday, August 7
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States -
Line Dancing with the Stompin’ Boots: Friday, August 7
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesLine Dancing with the Stompin' Boots