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Labor Day Weekend in Connecticut: Festivals, Fairs and More Things To Do with Kids

Fall fairs and Festivals are coming to Connecticut for Labor Day Weekend 2024! Photo courtesy of the Goshen County Fair
Fall fairs and Festivals are coming to Connecticut for Labor Day Weekend 2024! Photo courtesy of the Goshen County Fair
8/28/24 - By Jennifer Coe

Looking for the best things to do in this Labor Day Weekend in Connecticut? Here are some family-friendly events and activities to add to your list for this weekend.

Cool, crisp mornings are replacing hot, humid ones and can only mean one thing: the end of summer is here. Those of us who love this annual change are packing our schedules with fun places to go, like the Woodstock Fair and the Corn Maze and Cider Donut Festival at Lyman Orchards. Hungry kids would love for you to get tickets to the Pancake Breakfast at Lachat Farm or a HUGE turkey leg at the Connecticut Renaissance Faire! (Wear a costume!) 

Also opening this weekend is Fall Festival at the Big Red Barn at Bishop's Orchards, where you can find apple picking, wagon rides, pumpkin picking, and more.

To see what else is happening around the state, browse the Mommy Poppins Events Calendar. For the latest and best family-friendly activities, subscribe to our weekly newsletters and follow us on Facebook and Instagram. Have a wonderful Labor Day Weekend with your family!

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Good Grief! You'll be scratching your head trying to pick from these fun things to do in CT! Peanuts themed corn maze photo courtesy of Lyman Orchards
Good Grief! You'll be scratching your head trying to pick from these fun things to do in CT! Peanuts themed corn maze photo courtesy of Lyman Orchards

Top Things To Do in Connecticut Labor Day Weekend 2024

St. Leo's Fair in Stamford

Stamford
August 30 - September 2
Free admission to the church grounds gives visitors the opportunity to sample international foods, enjoy rides and carnival games, and try their luck in the Bingo Parlor.  READ MORE

Farm Day at Fish Family Farm in Bolton

Bolton
Saturday, August 31
Enjoy vendors, games, live music, food, live animals, tractor rides, all you can eat fresh FREE ice cream, face painting, art stations, and more.  All located on the beautiful Fish Family Farm in Bolton, CT. READ MORE

Fall Festival at the Big Red Barn at Bishop's Orchards

Guilford
Opens August 31
Come to the Big Red Barn at Bishops this Fall and get into the season! READ MORE

Woodstock Fair

Woodstock
August 31 - September 2
It's a Labor Day tradition: the Woodstock Fairgrounds! 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. READ MORE

Haddam Neck Fair

Haddam Neck
August 31 - September 2
All weekend long, there will be rides, concessions, petting zoo, children's activities, agricultural contests, entertainment, and more. READ MORE

Goshen Fair

Goshen
August 31 - September 2
A great country fair with loads of animals, food, entertainment, and rides. Enjoy this Litchfield County Labor Day tradition that features fireworks, pie eating contests, a draft horse show, and a lumber jack contest.  READ MORE

The Connecticut Renaissance Faire

Lebanon
August 31 - September 2
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 the old-fashioned way. READ MORE

Corn Maze and Cider Donut Festival at Lyman Orchards

Middlefield
August 31 - September 2
Lyman Orchards Corn Maze & Cider Donut Festival is coming. Stay tuned for the announcement to find out what this year's Corn Maze theme will be READ MORE

Madison Salute to Our Heroes

Madison
August 31 - September 14
Continuing a patriotic tradition, the Exchange Club of Madison is proud to salute our 2024 heroes under our Americanism service to the community. Individuals, Families and Businesses are invited to dedicate flags in tribute to their Heroes this September. This majestic display of flags honors those people and organizations that bring light and hope into our lives. READ MORE

Pancake Breakfast at Lachat Farm

Weston
Sunday, September 1
Celebrate the first anniversary of the Daniel E. Offutt III Education Center at Lachat Town Farm. To mark this milestone, they are hosting the 2nd Annual Pancake Breakfast. READ MORE

Labor Day Concert with United States Coast Guard Band

New London
Monday, September 2
The U.S. Coast Guard Band presents its annual Labor Day concert at historic Branford House at UCONN Avery Point.  The program features Tchaikovsky's "1812 Overture" along with music by Malcolm Arnold, Frank Ticheli, Ante Grgin, and more! READ MORE

Labor Day Concert and Fireworks in Orange

Orange
Monday, September 2
Town of Orange Labor Day Concert & Fireworks Show is scheduled for September 2nd, with a rain date of September 4th, at the Orange Fairgrounds. This year, the event will feature a Queen Tribute by Johnny Zatylny as Freddie Mercury, alongside a six-piece band from Montreal, Canada. READ MORE

Newtown Labor Day Parade

Newtown
Monday, September 2
Fire trucks, festive music, floats and more! The 58th Newtown Labor Day Parade will kick off promptly at 10:00 a.m. More information can be found on the parade website: newtownctlabordayparade.org or here for the parade program. READ MORE

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