There’s Still Time to Attend Connecticut’s Country Fairs 2019

Report by Paula Antolini, August 16, 2019, 10:19AM EDT

Connecticut’s Country Fairs 2019 (LAST UPDATED 8/19)

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. There will also be plenty of opportunities to learn about all the latest developments in farming and agricultural equipment to help make your next John Deere tractor purchase from Fastline an informed choice.

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.

Bridgewater Country Fair

August 16-18, 2019
Bridgewater Country Fair is a long standing tradition that preserves the character of the quintessential country fair.  Be sure to bring your appetite. Great food tents abound throughout the fairgrounds and feature their famous roast beef sandwiches, chicken breasts and hotdogs. The fun kicks off with the annual Bridgewater Fair Parade.

Hamburg Fair

August 16-18, 2019
A family-friendly event that showcases may agricultural traditions while highlighting top local talent and entertainment. Enjoy the Milestone Midway carnival rides and games, food concessions, pony rides; entries and exhibits for farm, animal, crafts, fruits, vegetables and more.

Wolcott Country Fair

August 16-18, 2019
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 22-25, 2019 
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 23-24, 2019
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’d expect, like tractor pulls, frog jumping contests and arts and crafts exhibits.

Terryville Lions Club Fair

August 23-25, 2019
This year, the Terryville Fair will feature all of the old favorites you’d 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; the local jeep dealer in ct will likely be glad of all this fanfare surrounding the type of vehicles they supply. All of this and great food and entertainment, too!

Haddam Neck Fair

August 30-September 2, 2019
The Haddam Neck Fair is celebrating its 104th 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

August 30- September 2, 2019
Celebrating its 156th 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

August 31- September 2, 2019
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 5-8, 2019
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 5-8, 2019
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 5-8, 2019
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 6-8, 2019
Old-fashioned agricultural fair with livestock, agricultural exhibits, horse show, horse drawing, art and photography show, farm displays, amusement rides, food, and entertainment.

Ledyard Fair

September 6-8, 2019
Country fair featuring midway, stage entertainment, livestock shows, exhibits and much more.

Four Town Fair

Somers – September 12-15, 2019
You’ll have one-of-a-kind fun at the four-day, Four Town Fair, one of Connecticut’s oldest fairs. See the 20th Annual Antique & Classic Car Show, a rockabilly performance from The Whiskey Rebels 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. And you won’t want to miss the Open Swine Show or the Women’s Skillet Throw. It’s fun for all!

Berlin Fair

September 13-15, 2019
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 21-22, 2019
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 20-22, 2019
The Guilford Fair offers midway rides, games and food, Cattle, Poultry, Sheep & Goats, Vegetables, Baking, Canning, Flowers, Arts & Craft, Needlework  and Photography exhibits. Antique tractor Pull and Show.

Durham Fair

September 26-29, 2019
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 4-6, 2019
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 4-6, 2019
Signifying the close of fair season, the Portland Fair gives enthusiasts one last chance to experience all the classic fair entertainment, food, exhibits, animals and activities for the year.


You can see the full calendar for 2019 at


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