The 2026 Littleville Fair Book Is Ready!
If you are looking for information about this year’s Fair, the Fair Book is the place to find it. Download your copy today!

We’re getting ready for the 2026 Littleville Fair!
Time is flying and the 2026 Littleville Fair will be here before you know it! We’re lining up crafters, artisans, equipment vendors, and food vendors. If you’d like to sign up, check out our Forms page.

Will there be a Demolition Derby this year?
There sure will! This year’s Demolition Derby will be on Saturday, August 8 starting at 5pm. Click here to check out this year’s Rulebook for more information how you can attend or take part in the crashingly great action!

Can businesses and individuals sponsor the Demolition Derby?
Absolutely! Click here to download the Sponsorship Form. Complete it and return it by July 18 to confirm your sponsorship.

How much fun is the Littleville Fair?
Check out the photo gallery of the 2025 Littleville Fair to see for yourself! Great people, terrific vendors, awesome music, and loads of fun for the whole family! That’s the Littleville Fair.

Check out the 2025 Littleville Fair Photo Gallery

Mark your calendar! The 2026 Littleville Fair will take place on August 7, 8, and 9, 2026.

Join us for loads of fun and good times at the Fair!

Here’s the current schedule for the 2026 Littleville Fair —we may make a few changes before the gates open, but this shows you how much great stuff will happen this year!

NO DOGS allowed on the Fairgrounds! (Unless a medical service dog.)

50/50 Raffle All Three Days!!
Two Bicycle Raffles on Saturday & Sunday!!

Dates of the Fair:  August 7, 8 & 9, 2025

Friday, August 7:
  4:00 pm:           Gates Open &
                                 Raising of the Flag Ceremony
 ALL DAY:            Petting Zoo, Family Jungle &
                                 Army Bounce House
  5:00 pm:           Two classes of Oxen Draws
  5:00 pm:           Truck Pull Weigh in, 6pm Start
  6-9 pm:              Line Dancing with the Stompin’ Boots
  6:00 pm:           Bingo in the Dining Hall
  7:00 pm:           Free Kids Under 12 Bicycle Raffle *
  8:00 pm:           Exhibit Hall Closes

  * Child must be present to win bicycle raffle

Saturday, August 8:
  7:00 am:           Gates Open
  7:00 am:           Breakfast at the Food Booth
  7:00 am:           Diesel Truck Pull Weigh In
                                 (pulling starts @ 9am)
 ALL DAY:           Petting Zoo, Family Jungle &
                                 Army Bounce House
  9:00 am:           Diesel Truck Pull Start
  9:00 am:           Four Classes of Oxen Draws
 10:00 am:          Exhibit Hall Opens
 10:00 am:          Dairy & Beef Cattle Show
 10:30 am:          Ox Teamsters Challenge
11am-3pm:        Christ Merenda and the Wheel
                                 (@ the stage)
   TBD:                   BBQ Chicken Dinner
                                 in the Dining Hall
12pm-3pm:        FREE Kids Face Painting
12pm-3pm:        FREE Arcadia Wildlife Birds
                                 of Prey Booth Open
12pm-3pm:        FREE Canvas Painting with
                                 Piece of My Art Studio
                                 (while supplies last)
12:30 pm:           Kids/Adults Pie Eating Contest
 1:00 pm:           Free Kids Under 12 Bicycle Raffle *
   1:15 pm:           Ed Popielarczyk’s Magic Show &
                                Balloon Sculpting
   2:30 pm:          Kids Pedal Tractor Pulls
  4:00 pm:          Women’s Fry Pan Toss
  4:00 pm:           Ed Popielarczyk’s Magic Show &
                                 Balloon Sculpting
       5-9pm:          October Mountain Band
                                 (@ the stage)
   5:00 pm:          Free Kids Under 12 Bicycle Raffle *
   5:00 pm:          Demolition Derby
                                 (12-3pm registration)
   8:00 pm:          Exhibit Hall Closes

  * Child must be present to win bicycle raffle

Sunday, August 3 Events:
7:00 am:                  Gates Open
7:00 am:                  Breakfast at the Food Booth
8:00 am:                 Antique Tractor Pulls
 ALL DAY:                Petting Zoo, Family Jungle &
                                      Army Bounce House
9-11:30am:              Pitoniak Brothers Band
 10:00 am:               Exhibit Hall Opens
 10:00 am:                Sheep Show
 10:00 am:                Horse Pulls
   11:00 am:               Beard Competition
  11:00 am:                Ed Popielarczyk’s Magic Show
                                      & Balloon Sculpting
   11:00 am:               Broom Weaving Demonstration
         TBD:                   Turkey Dinner in the Dining Hall
         TBD:                   K9 Demo
12pm-3pm:              FREE Kids Face Painting
12pm-3pm:            FREE Canvas Painting with
                                     Piece of My Art Studio
                                     (while supplies last)
12:00 pm:                Zucchini Contest Weigh Ins
12:00 pm:                Free Kids Under 12 Bicycle Raffle *
12:00 pm:                Janoah the Jester
2:30 pm:                  Free Kids Under 12 Bicycle Raffle *
12:30 pm:                Kids Potato Sack Race
12pm-3pm:          Whiskey Traveler Band
                                       (@ the stage)
  TBD:                         Wool Spinning Demonstration
1:00 pm:                  Jack n’ Jill Cross Cut Saw Competition
  TBD:                         Kids Mini Horse Pull & Free for All
  2:00 pm:                All Raffle Ticket Sales End
2:30 pm:                 Free Kids Under 12 Bicycle Raffle *
  2:30 pm:                 Ed Popielarczyk’s Magic Show
                                      & Balloon Sculpting
Afternoon:              Flower Box Winner & All Raffles Announced
                                     (when drawings are complete)
  4:00 pm:                 Exhibit Hall Pickup

  Child must be present to win bicycle raffle

Support the Littleville Fair and give yourself a chance to win great prizes!
Buy your raffle tickets today!

Get Your Tickets for the  2026 Littleville Fair Raffles!

Four Great Raffles, Four Great Prizes!

We’ve got four great raffles with terrific prizes to support  the Littleville Fair this year! The prizes and ticket prices are:

• 70-Quart Pelican Cooler.
  TICKETS: one for $5 or five for $20
  
  
• Folding Picnic Table.
  TICKETS: one for $5 or five for $20
  
  
• Stihl 20-inch MS 271 Chainsaw.
  TICKETS: one for $10 or five for $40

• Savage Arms Axis 2 Pro.
  TICKETS: one for $10 or five for $40

Raffles tickets will be on sale at the Pancake Breakfast, the Easter Egg Hunt, at all other fundraising events, or you can purchase them from the Littleville Fair Association. You will also be able to purchase tickets for these raffles at the Fair.

The drawing for the 2026 raffles will take place on Sunday, August 9, 2026

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Here’s everything you need to get ready for the 2026 Littleville Fair!

Dates of the 104th  Littleville Fair:
August 7, 8, & 9, 2026

Fairground Address:
15 Kinnebrook Road
Chester, MA 01011

Admission:
Adults:   $10.00
Children Ages 12 years & under:  Free

2026 Fair Hours:
  Friday, August 7:           4:00 pm – 10:00 pm
  Saturday, August 8:    7:00 am – 10:00 pm
  Sunday, August 9:        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 Organization Contacts:

Horse Pulls:
Kip & Mary Beth Porter ~ 413-297-4201

Oxen Pulls:
Josh Porter ~ 413-348-5767

Truck Pulls:
Paul & Randy LaPointe ~ 413-244-7412
Moe Sr. & Ted Boisseau ~ 413-364-4411

Exhibit Hall:
Nancy Boisseau ~ 413-297-2416

Vendors & Crafters:
Leslie & Jeff Stokowski ~ 413-433-8400

Gates:
Nancy Boisseau ~ 413-297-2416

Grounds Superintendent:
Moe Boisseau Jr. ~ 413-297-2415

Snack Bar & Dining Hall:
Mike Carpenter ~ 413-537-1771

Entertainment:
Steph Hunter ~ 413-627-7366

Littleville Fair Association Officers and Superintendents for 2026:
President:
Moe Boisseau Sr.  ~ 413-364-4411

Vice President:
Mike Carpenter  ~ 413-537-1771

Treasurer:
Jim Burke  ~ 413-207-2587

Secretary:
Corky Carpenter  ~ 413-537-1771

Littleville Fair Board of Directors 2026:
Sonny Lafond  ~ 413-552-9057
Bob Henrichon  ~ 413-667-5135
Nancy Boisseau  ~ 413-297-2416
Ted LaPointe  ~ 413-977-6093
Mike Lafond             

Auditors:
John Steins
Ted Boisseau