September GoList: The Best Things To Do with CT Kids this Month

Best Things to Do With Kids in Connecticut In September

September brings with it apple picking, fall fairs, hayrides, festivals, and many more fun outings. Our event calendar is a wonderful resource full of events for Connecticut families. Many of which are mostly free or inexpensive. Some September highlights include the Blues, Views, and BBQ Festival in Westport and for oyster lovers, the Annual Oyster Festival in Norwalk. 

Here you'll find 31 of our top picks of fun things to do with kids in Connecticut this September. Click through to the full listing so that you can add your favorites to your calendar. Be sure to sign up for our FREE newsletters so you can get all our CT picks delivered to your inbox.

Woodstock Fair—Woodstock
Friday, August 31 - Sunday, September 3, 2018
Held at the Woodstock Fairgrounds, the Woodstock Fair offers 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 including the biggest Ferris wheel around!

Fish Family Farm Day—Bolton
Friday, September 1
Spend the day on the Fish Family Farm and enjoy the animals, live music, hayrides, barn tours, games, and all the farm fresh ice cream you can eat.

Prudence Crandall DayCanterbury
Friday, September 1
Celebrate Prudence Crandall's birthday with music, crafts, old-fashioned lawn games, food, and tours of the museum.

Goshen Fair—Goshen
Saturday, September 1 - Monday, September 3, 2018
A great country fair with loads of animals, food, entertainment and rides. A Litchfield County Labor Day tradition. Fireworks, pie eating contests, draft horse show, lumber jack contest. Tons of country fair fun all weekend. New kids stage this year over by the antique barn.

CT Renaissance Fair—Lebanon
Saturday, September 1 - Sunday, October 14 (weekends), 2018
Step back to the past at The Connecticut Renaissance Faire. It's a time to play and unwind, to feast and drink, and a time to celebrate. 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 Connecticut family fun.

8th Annual Blues, Views, and BBQ Festival—Westport
Saturday, September 1 - Sunday, September 2, 2018
JESUP JAM at the Westport Library offers activities for every age; cooking demonstrations by top local chefs presented by the award-winning food blog CTbites, pie and rib eating contests, street performers, bouncy amusements, bull riding, kids’ activities, and a Kansas City Barbeque Society competition.

Mysterious Pendragon Society—Simsbury
Fridays in September, 2018
Join this unique book club and participate in themed activities based on a different book each month.

Connecticut Maritime Heritage Festival—New London
Wednesday, September 5 - Sunday, September 9, 2018
Festival will welcome up to 20 sturdy, sleek and fast vessels, first into Mystic Seaport where exciting, hands-on educational activities will take place.

Wapping Fair—South Windsor
Thursday, September 6 - Sunday, September 9, 2018
For 124 years this fair has been providing loads of family fun. You'll find racing ducks and pigs, jugglers, acrobats, two stages filled with live music, carnival rides, food and so much more!

Hebron Harvest Fair—Hebron
Thursday, September 6 - Sunday, September 9, 2018
Hebron Harvest Fair is a country agricultural fair featuring animal displays, various food, animal pulls, truck pulls, country music, and a carnival midway.

North Haven Fair—North Haven
Thursday, September 6 - Sunday, September 9, 2018
Join the fun at the 76th Annual North Haven Fair.  Enjoy a variety of exhibits, many animals - such as baby chicks, horse pulls, racing pigs and a petting zoo - great rides, scrumptious food, and live music.

Simsbury's Septemberfest—Simsbury
Friday, September 7 - Sunday, September 9, 2018
Enjoy this packed, three-day agenda of children’s activities, live musical entertainment, great food selection, Business Expo retailers, the Simsbury Chamber Home Improvement Show and so much more. And much of the event is FREE!

Ledyard Fair
Friday, September 7 - Sunday, September 9, 2018
Pie eating contests, oxen pulls, horseshoe pitching, and celebrating the town of's all at the Ledyard fair.  Don't miss the Little Miss Ledyard pageant and the Rabbit and Guinea Pig show.

Norwalk Seaport Association Annual Oyster Festival—Norwalk
Friday, September 7 - Sunday, September 9, 2018
The annual Norwalk Seaport Association Oyster Festival is a weekend chock full of activities and entertainment of all kinds for the whole family. The 2017 Oyster Festival will feature live music from dozens of bands on multiple stages as well as the return of aerial stunt artists the Nerveless Nocks Thrill Show, the popular Paul Bunyan Lumberjack Show with logrolling, axe throwing, tree climbing, dragster chain sawing, and more. In addition, there will be a Craft Beer tent featuring more than 25 beers, an expanded food court, the Kid’s Cove with rides and games, the largest ever Arts & Crafts Pavilion with more than 100 artisans and crafters, an oyster-slurping contest, and much more.

RetroWorld Gaming Expo—Hartford
Saturday, September 8, 2018
​Head over to the largest gaming convention in the state. All encompassing gaming expo featuring video games, cosplay, tournaments, kids freeplay area, live music, game shows, arcade and more.  

Harvest Music FestivalMiddlefield
Saturday, September 8
Enjoy the music and corn maze at this free festival. Plenty of activities for the whole family including pony rides, face painting, and fruit picking in the orchard!

Concert and River FirePutnam
Saturday, September 8, 2018
At dusk, the fire pots will be lit in the Quinebaug River with the mood setting music of "The East Woodstock Cornet Band," a family friendly crowd pleaser. 

St. Peter's Apple FestivalMonroe
Saturday, September 8 - Sunday, September 9, 2018
Craft vendors from all over the Northeast set up tents on the historical Monroe Green to sell everything from doll clothes to jewelry to woodcrafts. There are games for kids, tons of great food and baked goods, and apples, apples, apples!

RCA Ladrigan Swim Races and Family Fun Day—Rowayton
Sunday, September 9, 2018
The Lighthouse Race (a one-mile swim from Green’s Ledge Lighthouse to shore) starts at 10:30am sharp. Following the Lighthouse Race is the Buoy Race (a swim from the buoy to the shore). Last are the Children’s Swim Races, which are grouped by age and run parallel to the beach. After the awards ceremony, all are invited to join in the traditional beach games, which include a tug-of-war, a pie-eating contest, and an egg toss.

Four Town FairSomers
Thursday, September 13 - Sunday, September 16, 2018
Featuring various agricultural contests, livestock competitions, music, jugglers, a midway, and more. Music, entertainment and fun for the whole family at the annual Four Town Fair.
Cider Saturday—New Canaan
Saturday, September 15, 2018
There will be cider press demonstrations, old fashioned games, a pumpkin scavenger hunt, seasonal harvest crafts for kids, and even bake your own apple filled with sweet goodies.
Fall Festival and Hawk Watch WeekendGreenwich
Saturday, September 15 - Sunday, September 16, 2018
Enjoy this family-friendly nature festival where you can see live raptor shows, climb a climbing wall, take a hayride, go on a hike, and play fun games.
Newington Waterfall FestivalNewington
Saturday, September 15, 2018
Featuring food vendors, artists & crafters, children's activities, live entertainment and a Farmers Market. There's something for everyone at this fun-filled celebration. The day's highlight features the creation and judging of the "Artist's Chalk Walk." Watch as Market Square's pavement magically transforms into a colorful art gallery by artists young and old. Let your creativity flow! Two divisions are judged and awarded fabulous prizes.
Bristol Mum FestivalBristol
Thursday, September 20 - Sunday, September 23, 2018
This year's festival theme is "Home is Where the Heart Is" and events include live music, a carnival midway, food trucks, a car show, children's programming, and plenty more.

Lisbon Fall FestivalLisbon
Friday, September 21 - Saturday, September 22, 2018
After a 3.5 mile road race at the Lisbon Town Hall there will be activities for kids of all ages, including “Touch a Truck,” “Knocker Ball," a dodgeball tournament, and traditional games such as three-legged races, sack races, and bobbing for apples.

Wethersfield CornfestWethersfield
Saturday, September 22, 2018
For the young and young-at-heart there will be inflatable rides, a pumpkin patch, pony rides, hay rides and kids activities including a photo booth and dunk tank. Witness Wethersfield's up-and-coming musical acts and dancers, cheer on the WHS Band, and enjoy a great day of entertainment on the 2 stages!

Family Nature Day—Litchfield 
Saturday, September 22, 2018
Meet a bald eagle! The day is filled with live animals, guided nature walks, information booths, horse drawn wagon rides, and yummy food.

Annual Seymour Pumpkin FestivalSeymour
Sunday, September 23, 2018
The Seymour, CT Pumpkin Festival is a juried craft show with an average of 15,000 people in attendance each year. Each craft booth is given special consideration for placement, depending on their product. Craft booths include handmade jewelry, silk and dried flower arrangements, soft sculpture, quilts, paintings, blown glass, woodcrafts, Christmas ornaments, ceramic items, hand painted slate, and more!

Durham FairDurham
Thursday, September 27 - Sunday, September 30, 2018
In 1916 the Durham Fair began a tradition. That tradition continues today during the last full weekend in September when the fairgrounds come alive and magically transform into Connecticut’s largest agricultural fair. Come visit the Durham Fair and you’ll see what a real fair is all about. Live entertainment, rides and games on the Midway, first-class animal competitions and discovery events on the Corn Stalk Stage.

Ansonia Harvest Festival—Ansonia
Sunday, September 29, 2018
Enjoy a bounce house, batting cages, vendors, food, and music to commemorate the Harvest season.
Wee Faerie VillageOld Lyme
Saturday, September 29, 2018
Visitors of all ages marvel at the detail and craftsmanship as they explore over thirty hand-crafted, faerie-sized buildings nestled throughout the Florence Griswold Museum’s 13-acre historic site.