Kids Pedal Tractor Pull: Saturday, August 2
2025-08-02 14:30 - 15:30 UTC | Littleville Fairgrounds, 15 Kinnebrook Rd., Chester, MA, 01011, United States
Come cheer for the kids as they pedal their tractors through the pedal-tractor pull!

Farm Olympics: Saturday, August 2
2025-08-02 15:00 - 16:00

Henry the Juggler
2025-08-02 15:15 - 16:15

Women's Fry Pan Toss: Saturday, August 2
2025-08-02 16:00 - 17:00
Who will be the fry pan tossing champ? Be at the fair on Saturday at 4:00 pm to find out!

Ed Popielarczyk's Magic Show & Balloon Sculpting: Saturday, August 2
2025-08-02 17:00 - 18:00
Come prepared to be entertained and amazed!

Demolition Derby: Saturday, August 2
2025-08-02 17:00 - 19:00
Registration from 12pm-3pm.

Petting Zoo & Family Jungle: Friday, August 7
2026-08-07
Young 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 beast!

Gates Open & Raising of the Flag Ceremony: Friday, August 7
2026-08-07 16:00
Help us kick off the 2026 Littleville Fair and say Happy 250th Birthday to the USA!

Truck Pull Weigh In: Friday, August 7
2026-08-07 17:00 - 18:00
Truck Pull @ Littleville Fair
This event is free with admission to the fair.

Two Classes of Oxen Draws: Friday, August 7
2026-08-07 17:00 - 19:00
Two classes of oxen draws, 1,600 lbs and 2,000 lbs.
This event is free with admission to the fair.

Bingo in the Dining Hall: Friday, August 7
2026-08-07 18:00 - 20:00

Line Dancing with the Stompin’ Boots: Friday, August 7
2026-08-07 18:00 - 21:00
Line Dancing with the Stompin’ Boots

Kids Under 12 Bicycle Raffle: Friday, August 7
2026-08-07 19:00
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 Friday at 7pm for the drawing!

Exhibit Hall Closes: Friday, August 7
2026-08-07 20:00

Petting Zoo & Family Jungle: Saturday, August 8
2026-08-08

Gates Open: Saturday, August 8
2026-08-08 07:00

Breakfast @ Food Booth: Saturday, August 8
2026-08-08 07:00 - 09:00
Join us for breakfast at the Food Booth!

Four Classes of Oxen Draws: Saturday, August 8
2026-08-08 09:00 - 11:00
Four 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.

Diesel Truck Pull, Saturday, August 8
2026-08-08 09:00 - 11:00
Weigh in starts at 7:00am; pull starts at 9:00am

Exhibit Hall Opens: Saturday, August 8 @ 10am
2026-08-08 10:00

Beef & Dairy Cattle Show: Saturday, August 8
2026-08-08 10:00 - 12:00
Breed 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 too!

Ox Teamsters Challenge: Saturday, August 8
2026-08-08 10:30 - 12:00
Ox 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 for animals that stayed the night. Only oxen coming in for Saturday’s draw need to be weighed on Saturday.

Chris Merenda and The Wheel: Saturday, August 8
2026-08-08 11:00 - 15:00

Chicken BBQ: Saturday, August 8
2026-08-08 12:00 - 15:00
Join us for a tasty Chicken BBQ lunch in the Dining Hall!

Free Face Painting for Kids: Saturday, August 8
2026-08-08 12:00 - 15:00
FREE!

Arcadia Wildlife Birds of Pray Booth: Saturday, August 8
2026-08-08 12:00 - 15:00
FREE

Canvas Painting with Piece of My Art Studios: Saturday, August 8
2026-08-08 12:00 - 15:00
While supplies last. FREE!

Kids Under 12 Bicycle Raffle: Saturday, August 8
2026-08-08 13:00
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 1pm for the drawing!

Exhibit Hall Pickup: Sunday, August 9 @ 4pm
2026-08-08 16:00

Exhibit Hall Closes: Saturday, August 8
2026-08-08 20:00
