Connecticut’s Country Fairs 2021 Last Updated: October 2021

It’s that time of the year again when Connecticut welcomes the summer and fall seasons with carnivals, festivals, and fairs in every corner of the state.  With tons of activities, entertainment, live music, and delicious food, the only difficult choice will be deciding which ones to attend. Take the family to the same fair you went to as a child or check out a new one. Everyone can enjoy observing the animal exhibits up close, seeing an antique tractor pull or livestock show, taking in live music, perusing locally made food and even indulging in a piece (or two) of fried dough. Connecticut has agricultural fairs that are major fairs, district fairs, 4-H fairs, and local fairs. Here are some of the major fairs happening around the state. You can see the full calendar for 2021 at

North Stonington Agricultural Fair

July 8-11, 2021
The first fair of the season with great food, entertainment, livestock pulls, and exciting competitions.

Lebanon Country Fair

August 6-8, 2021
Since 1959, The Lebanon Lions Club has operated the Lebanon Country Fair.  Many local non-profit organizations utilize the fair as their main fundraiser so you can feel good about supporting worthy causes while having lots of fun.  Each year brings new and exciting things as well as the old favorites like oxen pulls and pig scrambles topped off with great entertainment, arts and crafts, and tasty fair cuisine.

Wolcott Country Fair

August 20-22, 2021
Begun in 1979, the Wolcott Country Fair is the area’s largest agricultural and family fun event of the summer. During the course of the annual three-day event, more than 30,000 people come to enjoy the fair’s sights and sounds. Attendees are treated to a traditional country fair complete with antique farm equipment displays, tractor pulls, pig racing, thrill rides, and plenty of food and entertainment.

Brooklyn Fair

August 26-29, 2021
Come experience the oldest, continuously active agricultural fair in the United States, featuring draft horses, livestock shows, home and garden exhibits, live entertainment, historical displays, special daily events, and of course, great food.

Chester Fair

August 27-29, 2021
The Chester Fair is a time-honored tradition in a quintessential small New England town that never disappoints.  Come see Robinson’s Racing Pigs and all the favorites you would expect as tractor pulls, frog jumping contests, and arts and crafts exhibits.

Terryville Lions Club Fair

August 27-29, 2021
This year, the Terryville Fair will feature all of the old favorites you would expect from a traditional country fair, as well as a few new surprises, like ATV and dirt bike drag racing, Jeep, and pickup truck tug-of-war competitions, and side-by-side truck racing. All of this and great food and entertainment, too!

Haddam Neck Fair

September 3-6, 2021
The Haddam Neck Fair is celebrating its 105th year and is known for its family-friendly atmosphere and beautiful setting. The many events offer something for everyone including tractor and truck pulls, horse and oxen pulling contests and a horse show. Animal exhibits and contests, like women’s skillet throwing, are popular. Vendors are on hand to offer vegetables, flowers, canned goods, and handmade arts and crafts. There’s live music and delicious food, too!

Woodstock Fair

September 3-6, 2021
Celebrating its 157th year, the state's second-oldest agricultural fair has tasty food, livestock shows, a petting zoo, free stage shows, a midway, go-kart races, strolling entertainers, plenty of vegetables, and flowers, and much more.

Goshen Fair

September 4-6, 2021
Major agricultural fair with livestock judging, draft horse show, woodcutting competition, entertainment, food vendors, midway, arts and crafts, home exhibits, and more. This celebration includes an adult spelling bee, fireworks, hay bale toss contest, parade, pie-eating contest, and a skillet throw contest.

Hebron Harvest Fair

September 9-12, 2021
This major agricultural fair is packed with fun and entertainment including livestock shows, a midway, exhibits, a small-animal barn, arts and crafts, food booths, and continuous stage entertainment.

North Haven Fair

September 9-12, 2021
Bring the kids to Old MacDonald’s Farm for a kids pie eating contest then visit the animals in the petting zoo. Enjoy live musical performances, agricultural exhibits, arts and crafts, and great fair food.

Wapping Fair

September 9-12, 2021
An agricultural fair featuring livestock, rides, bands, magic, food truck festival, exhibits, children's attractions, aerialist performance, exotic animal meet and greet, vendors, and more.

Bethlehem Fair

September 10-12, 2021
Old-fashioned agricultural fair with livestock, agricultural exhibits, horse show, horse drawing, art and photography show, farm displays, amusement rides, food, and entertainment.

Four Town Fair

Somers - September 16-19, 2021
You’ll have one-of-a-kind fun at the four-day, Four Town Fair, one of Connecticut’s oldest fairs. See the annual Antique & Classic Car Show and the Fair Parade. Like contests? There’s the Doodlebug Drawing Contest, Largest Frog & Frog Jumping Contest, Heaviest Pumpkin Contest, and even a Corn Eating Contest. It’s fun for all!

Berlin Fair

September 17-19, 2021
The Berlin Fair began in 1882 as a Harvest Festival, became a state agricultural fair in the early 1900s, and remains a much-anticipated event in central Connecticut. The packed schedule includes pie-eating contests, frog jumping, large animal and crafts exhibits, and live entertainment throughout the weekend.

Orange Country Fair

September 18-19, 2021
From the classic car show and tractor pulls to arts and crafts and animal displays, there is truly something for everyone at the Orange Country Fair. Enjoy live entertainment and all types of mouthwatering fair food.

Guilford Fair

September 17-19, 2021
The Guilford Fair offers midway rides, games and food, cattle, poultry, sheep and goats, vegetables, baking, canning, flowers, arts & crafts, needlework, and photography exhibits. Antique Tractor Pull and Show.

Durham Fair

September 23-26, 2021
Begun in 1916, the Durham Fair continues its tradition today as Connecticut’s largest agricultural fair. With rides and games, tractor pulls, three livestock barns, crafts, exhibits featuring baking, canning, photography and horticulture, and a wide selection of fair food, there’s a huge harvest to take in.

Harwinton Fair

October 1-3, 2021
The Harwinton Fair offers good old-fashioned fun for all! See the Pig Races, Antique Tractor Show, Rabbit Costume Contest, Oxen Draw, and Civil War Displays. Enjoy a magic show and bluegrass music after visiting the barnyard animals. Stop by the Country Store for a memento of your special day!

Portland Fair

October 1-3, 2021 - the 2021 Portland Fair has been canceled.
The Portland Fair gives enthusiasts one last chance to experience all the classic fair entertainment, food, exhibits, animals, and activities for the year.

Riverton Fair

October 8-10, 2021
Old-fashioned country fair on scenic Farmington River with exhibits, animals, vendors, food, midway rides, music, wood chopping events, and more.