Chester Fair

05/14/2026

We have been hard at work locking in some rocking bands for the 2026 Chester Fair. Check out our live entertainment lineup below!

Friday, August 28th
6:45 p.m. - 10:45 p.m.: GREEN HILL
90’s rock meets jam band spontaneity. We play the hits, then rewrite the rules.

Saturday, August 29th
12:00 p.m. - 3:00 p.m.: THE SHORELINE CONNECTION
Playing crowd pleasing hits from the 1960’s to 1990’s around the shoreline for 26 years.

3:45 p.m. - 6:45 p.m.: THE MICK LOUIS BAND
The Mick Louis Band is CT's Best 4 Piece Country Rock Group from Central CT!

7:45 p.m. - 10:30 p.m.: PLASTERCADE
Bringing the best ultimate rock experience to stages across the tristate area.

Sunday, August 30th
1:00 p.m. - 4:00 p.m.: SHINY METAL HINEYS
An acoustic Progressive Bluegrass Band from Deep River that plays original, traditional and unique cover songs.

4:00 p.m. - 5:00 p.m.: CHESTER DRUM CORPS
A favorite annual tradition not to be missed!

*Schedule subject to change*

05/12/2026

We have 20 student volunteers representing 6 different local high schools signed up for our Zero Waste Program. Grab a friend and earn your community service hours!

Bonus - you get free admission to the Fair!

Sign up here:

Earn community service hours! Get free admission to the fair! Bring friends and volunteer together! Sorting Station Ambassadors will be assigned to stations on the fairgrounds that will include 3 bins- food scraps, recyclables and trash. You will interact with and guide fairgoers how to dispose of i...

05/03/2026

We are so excited to see so many students signing up to volunteers for our Zero Waste Program! Thanks for the feature Haddam-Killingworth Now!

There are still a few slots left for those students interested! https://www.signupgenius.com/go/10C0B49A8AD2BA5FBC52-62911903-chester #/

Submitted by Kim Price (May 2, 2026) — The Chester Fair is calling on local high school students to help support its nationally recognized “Zero Waste Program” during this year’s…

04/28/2026

We are looking for a few more Zero Waste Student Volunteers to fill the remaining sorting station ambassador slots on Saturday (8/29) in the afternoon and Sunday (8/30). Please use the following link to sign up.

A special thank you to all of the amazing volunteers who have signed up so far!

https://www.signupgenius.com/go/10C0B49A8AD2BA5FBC52-62911903-chester #/

Attention local students! We need your help!

Volunteer with the Chester Fair’s trash-sorting program! You’ll help visitors figure out what goes in each bin—it’s simple, interactive, and a great way to meet people. Training is provided and is perfect for students looking to give back, build experience, and have fun at the same time!

Click here to sign up: https://www.signupgenius.com/go/10C0B49A8AD2BA5FBC52-62911903-chester #/

Send us a message with any questions!

04/24/2026

Chester Fair in the news! We are thrilled to be featured in this recent article talking about our Zero Waste Program.

“On August 28-30, the Chester Fair takes place and continues its Zero Waste Program. "We began in 2022 as the second traditional country fair in the U.S. (and the first in New England) to have a Zero Waste Program," says Kim Price, who spearheads the initiative. "By 2025, the Chester Fair recovered 75% of its waste by recycling, converting vendors to compostable service ware and food scrap collection."

♻️💚

Here are some destinations that “walk the sustainable walk,” where you can shop, dine, or attend an event honoring Mother Earth.

04/07/2026

Attention local students! We need your help!

Volunteer with the Chester Fair’s trash-sorting program! You’ll help visitors figure out what goes in each bin—it’s simple, interactive, and a great way to meet people. Training is provided and is perfect for students looking to give back, build experience, and have fun at the same time!

Click here to sign up: https://www.signupgenius.com/go/10C0B49A8AD2BA5FBC52-62911903-chester #/

Send us a message with any questions!

10/29/2025

https://venmo.com/u/Pulling-For-Anna

Venmo is a digital wallet that lets you make and share payments with friends. You can easily split the bill, cab fare, or much more. Download the iOS or Android app or sign up on Venmo.com today.

10/29/2025

BENEFIT TRACTOR PULL for ANNA KAESER

The Kaeser family welcomed baby Anna to their family on July 7. Unfortunately, she has spent most of her early life at CCMC waiting for life saving heart surgery. Her surgery was successful and thankfully is now recovering at home with her parents, Craig and Jane and her siblings John and Mary Jane. This little baby and her family have endured so much in the first 4 months of her life!!!

JOIN US FOR A BENEFIT TRACTOR PULL AT THE CHESTER FAIRGROUNDS

SATURDAY NOVEMBER 1 , 2025

8 AM WEIGH -IN

9 AM PULL STARTS

CLASSES 3.5 mph and 6 mph

3000,3500,4000,4500,5000,5500,6000,6500 (HEAVIER CLASS IF THERE IS INTEREST)

P.J. TRANSFER SLED

RULES: 20" HITCH HEIGHT, CUT TIRES ONLY IN 6 mph, WHEELIE BARS REQUIRED

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All money raised will go to Jane and Craig to help with Anna’s recovery.

$20 Hook fees.

Admission is free; Donations accepted.

FOOD for sale by CHESTER HOSE COMPANY: CASH ONLY

RAFFLE TABLE AND T-SHIRTS WILL BE THERE FOR PURCHASE: CASH ONLY

Watch for weather related updates in case the event is postponed!

08/24/2025

Another wonderful fair in the books! Thank you to all who joined us and all our volunteers for their hard work!!!

08/23/2025

The shirts are selling like hotcakes! Get one before they sell out!!!