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Connecticut fall fairs and festivals are back! After shutting down for 2020, many of our beloved local autumn events are reopening this year. Keep reading to discover 20 places to get your fall on this season!
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. For the most part, that approach works well for us.
And yet, we often hear from our readers about events that sound amazing, but that we just can’t possibly cover on the blog in the usual Out and About Mom style. Because you see, many of these events are so short-lived that by the time we could go there, collect all the details, edit all the photos and then get a blog posted about them, the event is over! Yet we still want to make sure you are getting the inside scoop on ALL the fun things to do in (and around) CT.
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 TWENTY fairs to try this season (in chronological order). Courtesy of our amazing Out and About Mom readers 🙂
Connecticut Renaissance Faire September 4 – October 17, 2021; (weekends, Labor Day & Columbus Day); Watch shows on stages around the faire, listen to minstrels playing in the streets and experience the old-world charm of a 16th century village filled with good, old-fashioned family fun–see jousting, live-flight birds of prey, comedy, magic and so much more. A family adventure for all ages awaits. Costumes are encouraged! 122 Mack Road, Lebanon
Wapping Fair September 9th-12th, 2021; 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
Hebron Harvest Fair September 9th-12th, 2021; 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
Cheshire Fall Festival September 10th-11th, 2021; The celebration begins on Food Truck Friday, September 10th 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 11th-October 31st, 2021; 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 for “The Ride” will be required and will open September 11th. 93 East High Street, East Hampton (BONUS! OAAM post from the 2013 event)
Four Town Fair September 16th-19th, 2021; Live music, contests, car show, food, games & rides and more. Four Town Fair Fairgrounds, 56 Egypt Road, Somers
Berlin Fair September 17th-19th, 2021; 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 17th-October 3rd, 2021; 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 (BONUS! OAAM post from the 2011 event)
Orange Country Fair September 18th-19th, 2021; 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 19th, 2021; Carnival rides and games, petting zoo, home-made crafts vendors, food, music, entertainment and more. French Memorial Park, 73 Spruce Street, Seymour
Durham Fair September 23rd-26th, 2021; 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 24th-26th, 2021; 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 October 1st-31st, 2021; Get ready to explore FOLLY WOODS! This year’s theme is a playful, miniaturized take on ornamental buildings popular on country estates, parks, and gardens in the 18th and 19th centuries. Visitors will learn about different architectural styles from across the world as they gaze in awe at the artists’ whimsical creative skills. Florence Griswold Museum, 96 Lyme Street, Old Lyme (BONUS! OAAM post from 2013 event)
Southington Apple Harvest Festival October 1st-3rd & 8th-10th 2021; 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) (BONUS! OAAM post from the 2013 event)
South Windsor Apple Harvest Festival October 2nd, 2021; Craft vendors, tons of food trucks, kids’ activities, live music, apple pie and more. 75 Brookfield Street, South Windsor
Scarecrows Along Main October 2nd – October 31st, 2021; 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 9th & October 11th, 2021; 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 15th-17th, 2021; Live music, amusement rides, food purveyors, the Harvest Pub, and the Angry Orchard 5K Road Race on the festival’s closing day. Please note, there will not be a craft vendor village this year due to construction taking place on the field. Riverfront Community Center, Welles Street, Glastonbury (Shuttle bus available from Glastonbury High School, 330 Hubbard Street)
Putnam Pumpkin Festival October 16th, 2021; Celebrate The Great Pumpkin with over 80 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 23rd, 2021; 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’re looking forward to sharing more reader recommendations in the future!
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