Seasonal Carnivals, Festivals, and Fairs

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Seasonal Carnivals, Festivals, and Fairs

Connecticut is an interesting state with many small communities with huge personalities and fascinating histories. During the summer and fall there are multiple carnivals, festivals and fairs that make for great staycations, interesting one-day outings close to home, or are easily turned into weekend getaways.

Loads of activities are offered for all ages in multiple subjects from health and wellness, education, culture, community, history, traditions, music, and art, always with plenty of food.  I find it difficult to choose which ones to attend whenever there are multiple events on the same day. Here are a few to grab your attention and interest along with links to help you research more wherever you might enjoy going:

Aug. 16-18. Bridgewater Country Fair, CT

The 68th Bridgewater Country Fair, August 16 – 18, 2019, is the Bridgewater Volunteer Fire Department’s annual fundraiser. The fun begins with a great parade (6:45 p.m. Friday, August 16) with Volunteer Fire Companies from Connecticut and New York showing off their newest trucks along with rare antique fire trucks and marching bands right down Main Street. This is a traditional country fair known for its great food, art, music, exhibits, death-defying tricks and thrills, a Goat Show, and local farmers competing with their produce and livestock, and more:

Aug. 30. Haddam Neck Fair

The 108th Haddam Neck Fair on August 30 offers something for everyone including women’s skillet throwing, sheep shearing, and watermelon eating contests along with a history walk, dino walk, and a horse show. They open early and go late into the night. Check out the schedule on their website:

Aug. 22-25. Brooklyn Fair, Brooklyn, Connecticut

The Brooklyn Fair held in Brooklyn, CT, August 22 – 25, began in 1809. It is considered the oldest continuously active agricultural fair in the United States, organized, and run by the Windham County Agricultural Society. They showcase draft horses, livestock shows, agility dog demonstrations, cattle show, home and garden exhibits, live entertainment, historical displays, and special daily events:

Aug. 23-24. Chester Fair, CT

See Robinson’s Racing Pigs and frog jumping contests.

Aug. 23-24. Terryville Lions Club Fair

ATV and dirt bike drag racing, Jeep and pickup truck-tug-of-war competitions and trucks galore

Aug. 31-Sept. 2. Goshen Fair

Includes a children’s stage productions, livestock judging, draft horse show, woodcutting competition, adult spelling bee, fireworks, hay bale toss contest, a pie eating contest and more:

North Haven Fair, September 5 – 8, 2019 Children love this Old MacDonald’s Farm with a pie eating contest, animal petting zoo, and racing pigs. There are live musical performances, competitions, and arts and crafts:

Sept. 5-8. Wapping Fair

Held at the South Windsor Fairgrounds in South Windsor, CT, made possible by the South Windsor Jaycees. It is an agricultural fair featuring livestock, rides, bands, magic, food truck festival, exhibits, children’s attractions, aerialist performance, exotic animal meet and greet, and special attractions JD Winslow Equestrian Entertainment and Magic of Christopher:

Sept. 12-15. Four Town Fair, Somers, CT

One of Connecticut’s oldest fairs with an Annual Antique & Classic Car Show, a rockabilly performance from The Whiskey Rebels, the Fair Parade and mud bogging. They are also known for their contests: The Doodlebug Drawing Contest, Largest Frog & Frog Jumping Contest, Heaviest Pumpkin Contest and Corn Eating Contest:   

Sept. 20-22. Guilford Fair

A great lineup including the Records & Burpee Zoo Show; Pine Meadow Children’s Zoo, IllusionQuest, Guilford Family Circus, Llama Show and Pony Drawing along with midway rides, games and food, cattle, poultry, sheep and goats, vegetables, baking, canning, flowers, arts and crafts, needlework  and photography exhibits, along with an antique tractor pull and show:

Sept. 26-29 Durham Fair

This fair began in 1916, has rides and games, monster truck ralley, talent contest auditions, live entertainment, three livestock barns, crafts, baking, canning, photography and horticulture, high school reunion, and a huge harvest of food that for the first time, this year includes Cousins Maine Lobster (Big Winners from TV’s Shark Tank) each day from 4:00 – 7 pm. There’s a real combination of old and new favorites:

Oct. 4-6. Harwinton Fair

Marks the end of the fair season. It dates back to 1853 and is a yearly project for the Harwinton Agricultural Society with piggy races, wood chopping, blacksmith shop, antique tractor show, rabbit costume contest, oxen draw and Civil War displays: Please let me know all about where you decide to go!

Information on upcoming events in New York and New Jersey:

New York Festivals, Fairs & Annual Events:

New Jersey Festivals, Fairs & Annual Events:


  • Sheryl Kayne

    Sheryl Kayne is a writer, editor, educator, and motivational speaker. She is the author of travel guidebooks. Immersion Travel USA: The Best & Most Meaningful Volunteering, Living & Learning Excursions was awarded The Society of American Travel Writers Foundation’s Lowell Thomas Travel Journalism Award for Best Travel Guidebook 2009 and Volunteer Vacations Across America was named on Amazon’s list of best new travel books 2010. Kayne travels extensively and works and volunteers where she visits. She was the writer-in-residence at the Everglades National Park, Homestead, Fla. and a writing fellow at the Helene Wurlitzer Foundation in Taos, N.M. She has appeared on NPR, CNN, CBN, ABC Weekend Evening News, Lifetime Television Network, and MTV, among others. Visit Sheryl at:

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