CHESTER, Mass. (WWLP) – The annual Littleville Fair in Chester begins Friday celebrating its 100th anniversary.

The fair kicks off at 4 p.m. Friday with live music, oxen draws, and the truck pulls start at 6 p.m. Gates open both Saturday and Sunday at 7 a.m. with a petting zoo, pony rides, touch-a-truck, and of course live music each day. There are plenty of things to do for kids that include free puppet shows/face painting/magic shows on Saturday and Sunday, quad/lawn tractor pulls Saturday night, and more.

The fairgrounds are located on 15 Kinnebrook Road in Chester. Adults are $8 and kids under 12 are free. Visit for a complete schedule of events.

  • Friday, August 5: 4 p.m. – 10 p.m.
  • Saturday, August 6: 7 a.m. – 10 p.m.
  • Sunday, August 7: 7 a.m. – 4 p.m.

A brand new snack bar, new barns, and new craft building is debuting this year and a parade will take place Saturday afternoon.