Antique Tractor Pull: Sunday, August 6
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesThe Western Mass Tractor Pullers Association will run an Antique Tractor Pull. The weigh-in starts at 8am and the pull starts at 9 am. Block pulls will use two boats. The pull order will be: 3500 8000 4500 9500 5000 11,000 5500 12,500 6500 14400 Heavy tractors will start early with two boat system
Horse Pulls: Sunday, August 6
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesYour chances to see heavy horses pulling their best. These pulls follow current Massachusetts Fairs Association Pulling Contest Rules. Cash prizes up for 1st through 8th place (NOTE: The number of places paid will depend on the number of teams competing. For example, if only four (4) teams pull, only four (4) places will be awarded.)
Ed Popielarczyk’s Magic Show: Sunday, August 6
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesCome prepared to be entertained and amazed!
Zucchini Contest: Sunday, August 6
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesHow heavy is your zucchini?
Free Face Painting for Kids: Sunday, August 6
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesKids Potato Sack Race
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesKids Mini Horse Pull
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesTime TBD: Afternoon
Kids Under 12 Bicycle Raffle: Sunday, August 6
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 to be at the Littleville Fair on Saturday at 6pm for the drawing!
Ed Popielarczyk’s Magic Show: Sunday, August 6
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesCome prepared to be entertained and amazed!
Flower Box Winner Announced
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesCome see who wins!
Littleville Fair Car Show
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesLittleville Fair Car Show September 16, 2023 :: 9am-2pm Gates open @ 9am for Show Cars, 10am for spectators Sponsored by L.P. Adams
Petting Zoo, Reptile Exhibit & Pony Rides: Friday, August 2
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesAll day! Stop by to cuddle the critters, meet the lizards, or have a pony ride! Available to visit the entire time the fair is open.
Two Classes of Oxen Draws: Friday, August 2
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.
Easter Egg Hunt
Littleville Fairgrounds 15 Kinnebrook Rd., Chester, MA, United StatesThe 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 StatesSunday, 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 Breakfast & Chester Hill’s Springfeld! You won’t get a better breakfast at a better price—and by eating a good, hearty breakfast, you will also help …