Apples, Pumpkins, and Corn Mazes: 50 Fall Fairs in Connecticut You Can't Miss

Courtesy of The Connecticut Renaissance Faire
Fall Fairs in Connecticut

Fall is an amazing time to be in Connecticut, with wonderful fairs and festivals nearly every weekend, celebrating the many aspects of Nutmeg life, from apples to pumpkins and beyond. Most of these have free admission, but charge small fees for specific rides or activities so you'll want to confirm that before heading out. Check out our complete Fall Fun Guide too for more ideas on how to enjoy the season!

1. Woodstock Fair—Woodstock
August 31-September 3, 2018
Enjoy agricultural exhibits (including a birthing center where you can view a cow birth a calf right before your eyes!), animal and farm equipment competitions, entertainment, music, food, and carnival rides!

2. Blues, Views, and BBQ—Westport
September 1-2, 2018
This annual tradition includes great music, children's entertainment, and amazing food on the banks of the Saugatuck River.  

3. Goshen Fair—Goshen
September 1-3, 2018
Enjoy a Litchfield County Labor Day tradition that features fireworks, animals, food, entertainment, rides, pie eating contests, a draft horse show, and even a lumber jack contest. 

Photo Courtesy of the Connecticut Renaissance Faire

4. CT Renaissance Faire—Lebanon
September 1-October 14, 2018 (weekends and holidays)
Step back in time and watch shows on numerous stages around the faire, listen to minstrels playing in the streets, and experience the ageless, old-world charm of a 16th century village filled with laughter, romance, and good, old-fashioned family fun in Connecticut.

5. Hebron Harvest Fair—Hebron
September 6-9, 2018
One of the largest fairs in Connecticut, the Hebron Harvest Fair features animal displays, food, truck pulls, country music, a carnival midway, and more. 

6. Norwalk Seaport Association Oyster Festival—Norwalk
September 7-9, 2018
If you love oysters, this annual festival in Veteran's Memorial Park is for you. But even if you don't, there are rides and entertainment for the kids, food and drink for the grownups, and an arts and crafts area for everyone. Sunday is kids' day and includes a special price for unlimited rides.

7. East Haven Fall Festival—East Haven
September 7-9, 2018
Spend three days celebrating fall with rides, games, and a full slate of live music, a car show, and more.

8. Septemberfest—Simsbury
September 7-9, 2018
This weekend-long celebration kicks off with fireworks on Friday night and includes a special Saturday "family day" where there will be bounce houses, games, and more.

9. St. Peter's Annual Apple Festival—Monroe
September 8-9, 2018
This annual event held on the historical Monroe Green includes craft vendors from around New England, a country kitchen stocked full of fresh baked goodies, and kids’ games, face painting, and a moon bounce. 

10. Family Fall Fun Fest—Waterbury
September 8, 2018
Aimed at younger children, this festival includes a petting zoo, climb-on pirate ships, trains, princess carriages, etc., and meet a firefighter and police officer, among other events. Play games to earn points for prizes! Food is available for purchase.

Photo Courtesy of Lyman Orchard

11. Harvest Music Festival—Middlefield
September 8, 2018
Lyman Orchard hosts this free, family-friendly festival that brings together great music, delicious food, an amazing corn maze and fun activities for kids! Admission is free, but small fees apply to some of the activities. 

12. Four Town Fair—Somers 
September 13-16, 2018
This annual family favorite is full of both agriculture and and midway attractions. The fair includes a classic car show, a doodle-bug pull, pumpkin contest, and more. 

13. Berlin Fair—Berlin
September 14-16, 2018
The Berlin Lions Club sponsors this annual event featuring concerts, a rodeo, pig races, livestock competitions, as well as all the regular fair attractions, including dozens of vendors, favorite fair food, and midway games and rides for all ages.

14. Fall Festival and Corn Maze—Rocky Hill
September 14- October 28, 2018 (weekends)
The fall festival at Fair Weather Acres includes a corn maze, pedal cars, a children's hay maze, jump pillow, pumpkin patch, hay ride, food, farm animals, and more.

15. Harvest Moon Festival—Naugatuck
September 14-15, 2018
 This annual festival on the Naugatuck Green is in its 35th year and features two days of food, fun, and entertainment for the whole family.

16. Cider Saturday—New Canaan
September 15, 2018
Celebrate apples at the New Canaan Nature Center! The day will include cider press demonstrations, old fashioned games, honey bee hive tours, apple baking, and more. 

17. Fall Celebration at Smyrski Farm—New Milford 
September 15, 2018
Fall Celebration will include free breakfast, lunch and many farm activities. Hot air balloon rides begin at 8 a.m. There will also be a birds of prey show, hayrides, and face painting.

18. Greenwich Audubon Fall Festival and Hawk Watch—Greenwich
September 15-16, 2018
Come to a family-friendly nature festival. There will be a raptor show, a hawk release, a petting zoo, rock climbing wall, hay ride, face painting, and more. 

19. Chrysanthemum Festival—Bristol
September 20-23, 2018
This year's theme is "Fall in Love with Bristol" and will feature a car show, children's activities, craft vendors, a carnival midway, delicious food, and stage entertainment. 

20. Lisbon Fall Festival—Lisbon
​September 21-22, 2018
Kids can enjoy a touch-a-truck event, Knockerball, dodgeball, and classic fall festival games such as three-legged races, bobbing for apples, and sack races. 35 local craft  and food vendors will be on-site.

21. Wethersfield Cornfest—Wethersfield
​September 22, 2018
​The Cornfest features inflatables, bouncy houses, pony rides, hay rides, fair food, local cuisine, face painting, henna, crafters, and local businesses!

22. Seymour Pumpkin Festival—Seymour
​September 23, 2018
Head to French Memorial Park for carnival rides & games, live entertainment, a petting zoo, children’s contests, arts & craft vendors, and a variety of food booths run by local civic, school, and non-profit organizations. Free admission.

23. Ridgefield's Giant Pumpkin Weigh Off—Ridgefield
​September 23, 2018
Ridgefield's Ballard Park is transformed into a fall festival where giant pumpkin and squash growers from around the region will compete for cash prizes. There will be music, vendors, and activities for kids. ​Free admission.

24. Durham Agricultural Fair — Durham
September 27-30, 2018
Connecticut's largest fair. It features live entertainment, rides, games, animal competitions, and discovery events on the Corn Stalk Stage, along with crafts, exhibits, shopping, and fun food.

25. Christ Church Tashua's 40th Annual Apple Festival—Trumbull
September 29-30, 2018
Homemade apple pies, caramel apples, quiches, fall produce, and crafts for sale. A Kids Zone, face painting, games, music and crafts for fun! Animals for adoption. Cool raffle prizes. Proceeds will be given to local charity organizations. Free admission.

26. Southington Apple Harvest Fest—Southington
September 28- October 7, 2018
The Southington Apple Harvest is a much-anticipated festival that takes place over two weekends and features mouth-watering apple fritters. (The apple fritter booth is open during the week as well.) You will find carnival rides, fireworks, entertainment, a variety of food vendors, contests, a parade, and arts and crafts booths. There is a shuttle service available from Southington High School.

Photo courtesy of the Hammonasset Festival

27. Hammonasset Festival—Guilford
September 29-30, 2018
The Hammonasset Festival honors Native American heritage and nature with a special focus on children and families. Each day begins with a Native American blessing and smudging ceremony. Free admission for children 12 and under.

28. Soupstock—Shelton
September 29-30, 2018
Once a summertime classic, this two-day festival has been reimagined for fall and features soup and other tasty treats, as well as musical entertainment and a huge Kids Zone with scheduled activities throughout the day. Free admission for children 12 and under.

29. Apple Harvest Festival in Tapping Reeve Meadow—Litchfield
September 29, 2018
Join the Litchfield Historical Society for their first annual Apple Harvest Festival. The day will include crafts, lawn games, and historical demonstrations in the newly opened Tapping Reeve Meadow. Free admission.

30. Ansonia Harvest Festival—Ansonia
September 29, 2018
Spend the day in downtown Ansonia enjoying bounce houses, music and more. Free admission.

31. Great Pumpkin Fair—Quaker Hill
September 29, 2018
An annual event held by the Quaker Hill Baptist Church, the main attraction is the huge tag sale and large selection of homemade baked goods. And, of course, it's a perfect spot to get your fall pumpkin! 

32. Ambler Farm Day—Wilton
September 30, 2018
Enjoy the apple slingshot, farm animals, make-your-own-scarecrow, hay rides, trebuchet (aka “Punki'n Chucker”), children’s crafts, a pumpkin patch, and food. 

33. Harwinton Fair - Harwinton
​October 5-7, 2018
Established in 1853, the Harwinton Fair is still going strong. Enjoy agricultural entertainment such as antique tractor pulls, draft horse displays, and livestock judging. Don't miss the women's skillet throw or the magic show on Saturday!

34. Greenwich Historical Society Fall Festival—Greenwich
October 6, 2018
The Greenwich Historical Society is hosting a grand reopening property with a fall festival that will include music, food, and a scarecrow making workshop. 

35. Pumpkins n' Pooches Autumn Fair and Dog Fest—Colchester
October 6, 2018
The Colchester Green hosts a unique local fair, sponsored by the Colchester Lions Club. Bring your pooch to compete in a variety of doggie contests, bring the kids to try their hands at a pumpkin decorating competition, and bring your appetite for some delicious food offerings. Don't forget the hay ride! 

36. The Auerfarm Fall Festival—Bloomfield
October 6, 2018
Spend a fall day on the farm where the entire family is sure to enjoy children's activities and games, touch a truck, entertainment, food, and more!

37. Groton Fall Festival—Groton
October 6, 2018
Perhaps the Granddaddy of all the fall festivals in Southeastern Connecticut, the Groton Fall Festival boasts activities to entertain the whole family, all day!  Check out the live music stage, and bring your camera for optimal photos of the family in the pumpkin patch.  Local tip: Get there early for the best parking or, take advantage of shuttles from nearby Grasso Tech.  

38. Fall Flavor Fest—East Haddam
October 6-7, 2018
Ring in October with a walk through the pumpkin patch or the not-so-scary hay maze that features hidden passages and narrow corridors. Food trucks will be onsite with lots of treats available for purchase. Free admission. 

39. Warren Fall Festival—Warren
October 6-7, 2018
Celebrate fall with lumberjack demos, antique tractor pulls, and pumpkin cannons, as well as craft and food vendors. 

Photo courtesy of the Garlic and Harvest Festival

40. Garlic and Harvest Festival—Bethlehem
October 6-7, 2018
Try the garlic ice cream! Come taste delicious food from multiple vendors, ride the carnival rides, and browse hand-made crafts. Located at the Bethlehem Fairgrounds.

41. Ekonk Hill Harvest Festival—Sterling
October 6-8, 2018
There will be a corn maze, face painting, crafts, scavenger hunts, animals, contests, and more! 

42. Buell's Orchard Harvest Festival—Eastford
October 6-8, 2018
​This weekend-long celebration features hayrides, apple and pumpkin picking, live music, chicken barbecue, face painting, apple cider donuts, and much more family fun.

43. Chowder Days—Mystic
October 6-8, 2018
Okay, chowder may not be every kid's favorite meal, but this event is hands down my husband's favorite fall tradition. He can indulge in some chowder while my children enjoy the nautical fabulousness of the Mystic Seaport setting. 

44. Fall Festival to Benefit Animals—Stratford
October 7, 2018
This event has grown from a small dog walk with a few booths to a wonderful day long event which features educational speakers, music, entertainment, over 90+ people/pet vendors, food, microchip clinic, a large silent auction, contests, pet adoptions, and more.

45. Tokeneke Elementary School's Pumpkin Carnival—Darien
October 13, 2018
This beloved school carnival includes amusement rides, a play area for preschoolers, a haunted house, and food from local restaurants and food trucks. Free admission.

46. New Pond Farm Harvest Festival—West Redding
October 13, 2018
Celebrate a fall day on the farm with livestock encounters, including a chance to take a horse-drawn wagon ride through the pasture, to visit with the farm’s own dairy cows and calves, and to watch the sheep get their fall shearing. There will be crafting activities as well.

47. Fall Fair—New Canaan
October 12-13, 2018
Enjoy pony rides, a haystack maze, human hamster ball racing, a zip line, and so much more at this annual celebration of all things autumnal at the New Canaan Nature Center.

 Bring the family out to the farm on a nice fall day, enjoy entertainment, games, hayrides, food and local 4-H groups displaying their work.  Take a walk through our corn maze and enjoy our 120 acres. - See more at: Fall Festival—Bloomfield
October 6, 2018
Bring the family out to the farm on a nice fall day, enjoy entertainment, games, hayrides, food, and more.

48. Glastonbury Applefest—Glastonbury
October 12-14, 2018
Rated one of the top events in the state, each year 15,000 attend the festival for the live music, 150 craft booths, a pie-eating contest and bake-off, amusement rides, pony rides, fireworks, 30 music bands, local beer and wine, and a bicycle scavenger hunt. Parking at Glastonbury High School.

49Great Pumpkin Festival—Putnam
October 20, 2018
A town-wide celebration including music, contests, crafts, art, and children's activities. Take your kids on the 90-minute Great Pumpkin Festival Railroad Express (additional fees apply). Free admission.

50. 15th Annual Pumpkin Festival—Prospect
October 20, 2018
Prospect is the place to be for this family-friendly event that includes a pumpkin-filled park, a vehicle parade, and more. Free admission. 


Post originally published 9/30/12.