2019 Country Fairs

One of the best perks about living in Connecticut is our transition from summer to fall. The leaves start to change, the weather gets a little bit cooler, and of course, fairs start to pop up across the state! Our Town Crier has composed a list of the most popular and well-known fairs in Connecticut for you and the whole family to enjoy.



August 22 - 25

Brooklyn Fair

Located in the quaint town of Brooklyn, Connecticut, the Brooklyn Fair is the oldest, continuously active agricultural fair in the United States. The weekend includes draft horses, livestock shows, home and garden exhibits, live entertainment, historical displays, special daily events and of course, great food!


August 23 - 25

Chester Fair

The Chester Fair is a time-honored tradition in a quintessential small New England town. Activities include Robinson's racing pigs and old-time favorites like tractor pulls, frog jumping contests, and arts and crafts exhibits.


August 23 - 25

Terryville: Lions Club Fair

This year, the Terryville Fair will feature all your old favorites as well as new surprises: 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, of course!


August 24

47th Annual Madison Antiques Fair 

The Madison Historical Society Antiques Fair, one of the Society's largest annual fundraiser, was established in 1971 with the goal of being the best antiques show in an outdoor venue. With many outstanding antiques exhibitors from the Northeast, New York State, the mid-Atlantic states, and Florida, this unique fair typically offers eighteenth- and nineteenth-century American and European furniture; cottage and country furniture in paint and original finish; vintage garden and patio furniture and accessories; wicker; Victorian and vintage cast iron and wrought iron furniture; mid-twentieth-century Modern furniture; antique carpets and rugs. Fashion enthusiasts will find vintage designer costume jewelry and handbags; and vintage clothing, shoes, and hats.


August 30 - September 2

Haddam: Neck Fair

The Haddam Neck Fair is celebrating its 105th year and is known for its family-friendly atmosphere and beautiful setting. This year will feature tractor and truck pulls, horse and oxen pulling contests, and a horse show. There will also be animal exhibits and contests (like women's skillet throwing, which is always a fan favorite!) Vendors are also on hand to offer vegetables, flowers, canned goods and handmade arts and crafts.


August 30 - September 2

Woodstock Fair

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 for the entire family.


August 31-September 2

Goshen Fair

The Goshen fair is a family-centered agricultural fair with livestock judging, a draft horse show, a woodcutting competition, entertainment, food vendors, midway, arts and crafts, home exhibits, and more. The celebration also includes an adult spelling bee, fireworks, hay bale toss contest, parade, pie eating contest, and a skillet throw contest.


September 5 - 8

2019 Hebron Harvest Fair

The Hebron Harvest fair features arts and crafts, contests, livestock shows, food vendors, rodeo, traditional demolition derby, and tons more for the whole family to enjoy. In addition, live music will rock the 2019 Hebron Harvest Fair with a variety of concerts on all four days. 


Cotton Candy


September 5 - 8

North Haven Fair

The North Haven Fair is a major agriculture fair with daily entertainment, exhibit buildings and booths. There is also a midway, food, tractor pull, arts and crafts, live entertainment, and “Old McDonald's Farm” for the kid’s!


September 5 - 8

Wapping Fair

Located in South Windsor, the annual Wapping Fair features livestock, rides, bands, magic shows, food truck festival, exhibits, children's attractions, exotic animal meet and greets for the kids, vendors, an aerialist performance, and even more!


September 6 - 8

Bethlehem Fair

This year’s Bethlehem fair includes livestock, agricultural exhibits, a horse show, horse drawings, farm displays, amusement rides, food, and entertainment. There will also be an art and photography show, which is unique to the Bethlehem Fair.


September 13 - 15

Four Town Fair

You’ll have one-of-a-kind fun at the Four Town Fair in Somers, CT. There will also be plenty of opportunities to participate in our contests: Doodlebug Drawing Contest, Largest Frog & Frog Jumping Contest, Heaviest Pumpkin Contest and even a Corn Eating Contest.


September 13 - 15

Berlin Fair

The Berlin Fair began in 1882 as a Harvest Festival and became a much-anticipated event in central Connecticut. This year’s schedule includes pie-eating contests, frog jumping, large animal and crafts exhibits and live entertainment throughout the weekend.


September 13 - 29

The Big E

The Big E is always a family favorite! Located in West Springfield, Massachusetts, the Big E is a full day of fun. Along with games, rides, fair food, and the "state buildings," there will also be a car show, wine and cheese bar, concerts, and parades this year. There is also an agricultural building where the kids can pet animals and watch a horse show.


September 21 - 22

Orange Country Fair

From the classic car show and tractor pulls to the arts and crafts and animal displays, there is truly something for everyone at the Orange Country Fair. Enjoy live entertainment and fair food, as well as new events every hour.


September 20 - 22

Guilford Fair 

Connecticut's 2nd oldest agricultural fair is back for another year of fun! Each day will have entertainment, music, vendors, contests, food, and more! Highlights include the Zoo show, the family circus, and "Hilby" the clown. 


September 26 - 29

Durham Fair

Founded in 1916, the Durham Fair continues its tradition today as one of Connecticut's most popular fairs. With rides and games, food, tractor pulls, three livestock barns, crafts, exhibits featuring baking, canning, photography and horticulture, there's a huge harvest to take in!


September 28 - 29

Cannondale Foliage Arts and Crafts Fair

Located just a half-hour from Westport, the Cannondale Foliage Arts and Crafts Fair welcomes local artisan and craftspeople every year to sell high-quality arts and crafts products. Plus, admission is free!


October 4 - 6

Harwinton Fair

The Harwinton Fair offers old-fashioned fun for all! See the popular pig races, antique tractor show, rabbit costume contest, oxen draw and historical civil war displays. There will also be a magic show, bluegrass music, and a store to purchase all your favorite mementos.


October 4 - 5

Harvest Fair

It's that time of the year again! Bring the kids and join us for our FIFTH ANNUAL HARVEST FAIR at the Pilot House Community Farm. A fun time for the whole family! There will be hayrides, pony rides, food, games, fun and more!


November 23

The Ridgefield Woman’s Club 49th Annual Craft Fair

Conveniently located in Fairfield County, the Ridgefield Woman’s Club Fair includes a juried craft show with 100+ vendors. Items include pet and children’s’ gifts, food gifts, home décor, holiday gifts, knits/quilts, jewelry, pottery, photography, and much more. Refreshments and light lunch also available for purchase.






What's your favorite fair in Connecticut? Let us know on Facebook or Instagram at @ourtowncrier. 


1 Review
Trumbull, CT
Thank you for the variety

Great variety of fairs across CT to take the kids. Thank you for including so many fairs on different dates

July 2018

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13 Aug 2019

By Haley Falls