Fall Fairs in Connecticut 2023

Fall is such an exciting season in Connecticut! Practically every weekend from September through October there is a new local fair or festival to check out. And since these events are the epitome of family-friendly entertainment, that means we don’t have to try hard or go far to find something fun to do with our kiddos all season long.

If you’re a fan of our blog, then you probably know that in general, we mostly write about destinations and activities that we have actually been to and experienced firsthand. We like to be on the ground, getting all the nitty-gritty details and making sure that each outing is worth your time and expense. And yet, with so many events happening each fall in our state, we can’t possibly make it to all of them.

So sometimes we just have to do things a little differently around here. Like letting our readers make the recommendations for a change! Because if we can’t be there ourselves, having our readers voice their opinions is the next best thing 🙂

So today, I’m sharing a list of reader-recommended fall fairs and festivals. We’ve been to some of these places ourselves, but certainly not all of them. If these events are good enough to earn your praise though, then they are definitely worth putting on our “to go” list!

Here are 20 fall fairs to try this 2023 season (in chronological order). Courtesy of our amazing Out and About Mom readers 🙂

If you try out one of these fairs this fall, please let us know what you thought (and be sure to include any helpful tips!) by leaving us a comment on this post. And if you have a favorite fair to add (for this year or next), please tell us that as well.

The Big List of CT Fairs & Festivals (Fall Edition)

Connecticut Renaissance Faire September 2nd – October 15th, 2023; (weekends, Labor Day & Indigenous Peoples Day); Step back in time to a 16th-century harvest festival at Connecticut Renaissance Faire’s 25th anniversary celebration! Since 1999, they’ve been the gateway to a magical world where you can shop in New England’s largest Medieval Marketplace, feast on juicy turkey legs and craft beers, and enjoy hilarious comedy and thrilling acrobatics on 12 stages. All ages can enjoy the magic of the Renaissance – costumes are encouraged, but not required. Don’t miss out on an enchanted journey to the days of yore and celebrate with some good, old-fashioned fun. 122 Mack Road, Lebanon

Hebron Harvest Fair September 7th-10th, 2023; Live music, rides, a variety of food vendors, beer & wine garden, animal competitions, shopping at local vendor booths, chick hatchery, hay maze, Demolition Derby. Hebron Lion’s Fairgrounds, 347, Gilead Street, Hebron

Wapping Fair September 7th-10th, 2023; Food festival with more than 15 vendors, rides, live music & entertainment, petting zoo, magic, kids’ activities, livestock shows and more. John J. Mitchell Fairgrounds, 75 Brookfield Street, South Windsor

Cheshire Fall Festival September 8th-9th, 2023; The celebration begins on “Food Truck Friday,” September 8^th and continues Saturday. Craft and vendor booths on display, food and drink, a Car Show for all car enthusiasts, demonstrations, musical performances, carnival and more. Bartlem Park, 520 South Main Street, Cheshire

Pumpkintown USA September 23rd-October 31st, 2023; The Pumpkinheads are back in the Village and looking forward to your visit. And, you’ll be able to drive through the Pumpkintown Forest again this year! Reservations required for the drive-through Pumpkintown Forest activity (what was formerly known as “The Ride”). Admission to the Village can also be purchased in advance online.  93 East High Street, East Hampton 

Four Town Fair September 14th-17th, 2023; The Four Town Fair (Somers, East Windsor, Enfield and Ellington) is considered the oldest continuous Agricultural Fair in Connecticut! Enjoy live music, contests, car show, food, games & rides and more.  Four Town Fair Fairgrounds, 56 Egypt Road, Somers

Berlin Fair September 14th-17th, 2023; Rides and games for all ages, live music, a huge variety of food choices, craft exhibits, contests, livestock competitions and more. 430 Beckley Road, East Berlin

The Big E September 15th-October 1st, 2023; This is THE big one. Rides, carnival games, animal expositions, competitions, live entertainment, the Avenue of the States and food, food, food, food, food! 1305 Memorial Avenue West Springfield, MA

Orange Country Fair September 16th-17th, 2023; Pancake breakfast, craft exhibits, antique cars, tractor pulls, contests, flower and vegetable exhibits, wide variety of food vendors and more. 525 Orange Center Road, Orange

Seymour Pumpkin Festival September 17th, 2023; Carnival rides and games, kids’ activities, home-made crafts vendors, food, music, entertainment and more. French Memorial Park, 73 Spruce Street, Seymour

Durham Fair September 21st-24th, 2023; Live entertainment, rides and games on the midway, animal competitions and discovery events on the Corn Stalk Stage. Along with a trove of crafts, exhibits, shopping and fun food. Durham Fairgrounds, 24 Town House Road, Durham

Bristol Mum Festival September 22nd-24th, 2023; Live music, food, kids’ zone, game booths, petting zoo, pony rides, hay rides, crafts, community vendors and more. North Main Street and the surrounding area, Bristol

Wee Faerie Village September 30th-October 29th, 2023; Get ready to explore Fathom Heights: The wonderful underwater world of the sea faeries. 06H20 is the Connecticut zip code for a fashionable shoreside community where the wee sea faeries—enchanted creatures sporting both wings and fins—live, work, and play. From shell encrusted houses and coffee shops to kelp-covered schools, theaters, and sport arenas, you’ll love visiting this underwater wonderland. Florence Griswold Museum, 96 Lyme Street, Old Lyme 

Southington Apple Harvest Festival September 29th-October 1st & October 6th-8th 2023; Over the course of two weekends each autumn, the festival offers a wide variety of live music & entertainment, food, contests, crafts, children’s activities, parade, arts & crafts show and more. 75 Main Street, Southington (Shuttle bus available from Southington High School at 720 Pleasant Street) 

South Windsor Apple Harvest Festival September 23, 2023; Craft vendors, tons of food trucks, kids’ activities, live music, apple pie and more. 75 Brookfield Street, South Windsor

New Canaan Nature Center Fall Fair September 30th & October 1st , 2023; Join the New Canaan Nature Center for two days of traditional family fun at their 53rd Annual Fall Fair! Come and enjoy Carnival Rides, Crazy Maze, Zip Line, Apple Slingshots, Pumpkin Decorating, Spooky Stroll and so much more! Food, drinks, & snacks will be available for cash purchase as well. Rain or shine. 144 Oenoke Ridge, New Canaan

Scarecrows Along Main October 1st – October 31st, 2023; Come to the historic district of Wethersfield this October and see something spectacular! Scarecrows will be popping up alongside shops, restaurants, museums, colonial homes and more this fall season. Enjoy food and treats from local eateries as you stroll among these spooky, silly and whimsical creations! Main Street, Old Wethersfield (BONUS! OAAM post from the 2020 event)

Buell’s Orchard Harvest Festival October 7th-9th, 2023; Live music, famous chicken barbecue, wagon rides to apple picking and the pumpkin patch, apple cider, donuts and more. 108 Crystal Pond Road, Eastford

Glastonbury Apple Harvest Festival October 13th-15th, 2023; A Best of Hartford 2023 winner! Three stages of live music, amusement rides, petting zoo, food purveyors, craft vendors, the Harvest Pub, and the Angry Orchard 5K Road Race on the festival’s closing day. Riverfront Community Center, Welles Street, Glastonbury (Shuttle bus available from Glastonbury High School, 330 Hubbard Street)

Putnam Pumpkin Festival October 21st, 2023; Celebrate The Great Pumpkin with over dozens of arts and crafts vendors, music, pumpkin features in specialty boutiques and food & drink specials in unique Putnam restaurants! Ride the train and spend the day Discovering Putnam. Downtown Putnam

Plainville PumpkinFest October 21st, 2023; Outdoor festival featuring a kids’ costume parade, kids’ games, a variety of food trucks, carve your own pumpkin, a haunted house and many local vendors. Plainville Municipal Center, 1 Central  Square, Plainville

If you try out one of these fairs this fall, please let us know what you thought by leaving us a comment on this post! And if you have a favorite fair to add (for this year or next), please tell us that as well.

We look forward to continuing to expand this list to include all our reader favorites!

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