2021 Littleville Fair Is a Go!

The 2021 Littleville Fair Is a Go!!

The Littleville Fair is BACK! After much thought and careful consideration, the Officers and Directors of the Littleville Fair have set the dates! The fair will take place Friday-Sunday, August 6, 7 & 8, 2021!

This year’s fair will be full of all the fun and festivities you love. Of course, we’re planning a spectacular celebration for the return of the fair, but the health and safety of our exhibitors, staff, and visitors will still be a priority.

We’ll bring you more new about the events and the schedule for the  2021 Littleville Fair soon!

Check back often so you don’t miss a minute of the fun!

Annual Pancake Breakfast

Sunday, May 2 2021 ::   7 AM – Noon
@ The Fairgrounds, 15 Kinnebrook Rd, Chester, MA

Littleville Fair Annual Pancake BreakfastJoin us for the Annual Littleville Fair Fundraising Pancake Breakfast! You won’t get a better breakfast at a better price–and by eating a good, hearty breakfast, you will also help the Littleville Fair put on a bigger and better fair come August! Be sure to mark May 2 on your calendar and plan to show up early  and eat your fill!

Check out this delicious menu:

* Pancakes!
* Bacon
* Sausage
* Eggs
* Breakfast beverages

The only thing better than the food is the price:

General Admission (11 years and up):      $8
Kids aged 6-10 years old:                              $5
Kids under 5 are free!

At those prices, you’ll be able to eat hearty. Join us at the Fairgrounds on Sunday, May 2 for a great breakfast. Make every bite count to support the Littleville Fair!

2021 Raffles & New Contests

This year we are doubling your fun with two great new contests and two terrific raffles!

Scroll down for details

New Contests

There will be two terrific contests at the 2021 Littleville Fair: The Flower Box Contest and the Largest Zucchini Contest!

Polish up that green thumb and get growing!

The Flower “Box” Contest

Window box, giant pot, old toolbox or whatever you’ve got. Grab your favorite container and plant some flowers.

Flower “box” entries will be placed outdoors throughout the fairgrounds to be enjoyed by all. The three top winners will be voted on by fair attendees.

Flower Box Contest

The Largest Zucchini Contest

The bigger, the better! All zucchini entries will be weighed and judged with prizes awarded for the top three heavyweights.

Stay tuned for more details soon!

Zucchini Contest


This year the there will be two terrific raffles to support the 2021 Littleville Fair! Check out these great prizes!

Tickets for both raffles will be on sale at the Pancake Breakfast, at other fundraising events, or from the Littleville Fair Association any time before the start of the 2021 Littleville Fair. You will also be able to purchase tickets for these raffles at the Fair.

The drawing for both raffles will take place on August 8, 2021.

First: The Littleville Fair BIG Raffle

Two great prizes  in one raffle! You can win either a pair of wooden Adirondack Chairs or a 5-piece Lodge Cast Iron Cooking set (including an 8″ skillet, a 10.25″ skillet, a 10.5″ griddle, and a 10.5″ Dutch oven with lid).

Tickets Prices for the BIG Raffle:  $5 for 1 ticket or $20 for for 5 tickets 

Second: The Littleville Fair Gun Raffle

The prizes for this raffle are two good-quality rifles. The first is a Charles Daly 12 Gauge with a 28″ barrel, a vented rib-front bead sight and hardwood furniture. The second is a 22 Slug Stainless Camo, a fully rifled, bolt-action slug gun designed for 2 3/4″ and 3″ shells. It has a rugged synthetic stock with improved ergonomics and AccuStock, a user adjustable AccuTrigger, a Mossy-Oak Break-up Infinity camo stock, a button-rifled barrel,  a detachable magazine box, thread-in barrel headspacing, AccuFit technology with adjustable length-of-pull and comb height. 

Tickets Prices for the Gun Raffle:  $10 for 1 ticket or $40 for for 5 tickets 

BIG Raffle Tickets: $5 for 1 ticket / $20 for 5 tickets
Gun Raffle Tickets: $10 for 1 ticket / $40 for 5 tickets

Drawing will take place on August 8, 2021

Versatility Horse & Rider Competition

Saturday, August 7, 2021
@ The Fairgrounds, 15 Kinnebrook Rd, Chester, MA

Versatility Horse and RiderThe Littleville Versatility Horse & Rider Competition will be held on Saturday, August 7, 2021 at the Littleville Fairgrounds!

The Versatility Horse & Rider Competition is an obstacle course set up to challenge a horse and rider’s adaptability and skill when faced with various obstacles. The goal is to negotiate your horse successfully through the course of obstacles set up. Horse and rider teams receive a score for each obstacle completed based on the ease and accuracy of the task. The horse and rider team that accumulates the highest score is the winner.

Ribbons will be awarded to the top eight horse and rider teams in each class. The Jackpot Class will offer a payout to the top two team and ribbons to eighth place.

Come join the fun!!

Contact & Fair Info

Here’s everything you need to know about the 2021 Littleville Fair!

Dates of the 2021 Fair:
August 6, 7 & 8, 2021

Fairground Address:
98th Annual Littleville Fair
15 Kinnebrook Road
Chester, MA 01011

Adults:   $7.00
Children Ages 12 years & under:  Free

2021 Fair Hours:
  Friday, August 6:           4:00 pm – 10:00 pm
  Saturday, August 7:    7:00 am – 10:00 pm
  Sunday, August 8:        7:00 am – 4:00 pm

And here’s our contact information!

General Contact:
15 Kinnebrook Road
Chester, MA 01011
Phone:  413-667-3193
Email: thelittlevillefair@gmail.com

Littleville Fair Association Officers and Superintendents for 2020:
President                    Moe Boisseau Sr.            413-364-4411
Vice President         Mike Carpenter               413-862-4794
Treasurer                    Jim Burke                            413-207-2587
Asst. Treasurer        Irv Williams                        413-207-2471
Secretary                   Corky Carpenter              413-862-4794
Asst. Secretary       Betsy LaPointe                 413-210-0226
Grounds                      Moe Boisseau Jr.              413-297-2415

Littleville Fair Board of Directors 2020:
Sonny Lafond          413-552-9057
Bob Henrichon        413-667-5135
Nancy Boisseau      413-297-2416
John Steins                413-230-9835
Jeff Comee                413-427-5336
Randy LaPointe       413-244-7414
Ted LaPointe             413-977-6093

Adults:   $7.00
Children Ages 12 years & under:  Free

2021 Fair Dates & Hours:

  Friday, August 6:           4:00 pm – 10:00 pm
  Saturday, August 7:     7:00 am – 10:00 pm
  Sunday, August 8:        7:00 am – 4:00 pm