2019 Event Schedule
Events
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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
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Kids Under 12 Bicycle Raffle: Friday, August 7
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesWhat 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 …
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Petting Zoo & Family Jungle: Saturday, August 8
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: Saturday, August 8
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States -
Breakfast @ Food Booth: Saturday, August 8
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesJoin us for breakfast at the Food Booth!
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Four Classes of Oxen Draws: Saturday, August 8
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesFour classes of oxen draws: 2,400 lbs, 2,800 lbs, Youth, 3,200 lbs, and Free-for-Fall. This event is free with admission to the fair.
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Diesel Truck Pull, Saturday, August 8
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesWeigh in starts at 7:00am; pull starts at 9:00am
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Beef & Dairy Cattle Show: Saturday, August 8
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesBreed classes for Ayrshire, Brown Swiss, Guernsey, Jersey, Holsteins, and Milking Shorthorns. Classes for heifers, yearlings, dry cows, and cows by age, dam & daughter, sire, and more. Showmanship classes …
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Ox Teamsters Challenge: Saturday, August 8
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesOx Teamsters Challenge for Kids and Adults. Kids (Class A) offers Showmanship, Trained Steer, and Cart classes. Adults (Class B) Challenge Class. Friday's weight will hold over to Saturday's draw …
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Chris Merenda and The Wheel: Saturday, August 8
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United States