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Labor Day Weekend 2025 in Connecticut: Festivals, Fairs and More Things To Do with Kids

Fall fairs and Festivals are coming to Connecticut for Labor Day Weekend 2025! Photo courtesy of the Goshen County Fair
Fall fairs and Festivals are coming to Connecticut for Labor Day Weekend 2025! Photo courtesy of the Goshen County Fair
8/27/25 - 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.

All the summer activities are coming to an end, but that's GREAT because it means all the FALL things are starting! Those of us who love this annual change are packing our schedules with fun places to go, like the Woodstock Fair, the Corn Maze and Cider Donut Festival at Lyman Orchards and the Bishop's Fall Festival in Guilford.

Looking to celebrate Labor Day with your family? On Monday, check out Newtown Labor Day Parade or the Labor Day Concert with United States Coast Guard Band at Avery Point. To see what else is happening around the state, browse the Mommy Poppins Events Calendar or subscribe to our weekly newsletters and follow us on Facebook and Instagram. Have a wonderful Labor Day Weekend with your family!

 

More Things to do in Connecticut this Week with Kids 

 

 

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Top Things To Do in Connecticut Labor Day Weekend 2025

St. Leo's Fair in Stamford

Stamford
Through Saturday, August 30, 2025
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

Woodstock Fair

Woodstock
Thursday to Monday, August 28 - September 1
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
Friday to Monday, August 29 - September 1
All weekend long, there will be rides, concessions, petting zoo, children's activities, agricultural contests, entertainment, and more. READ MORE

Farm Day with the Lutz

Bolton
Saturday, August 30, 2025
Join the Lutz for our biggest annual fundraiser: Farm Day 2025! Admission includes unlimited farm fresh ice cream, barn tours, hayrides, live music and more! The beautiful Fish Family Farm in Bolton, CT will be full of things to do all day. READ MORE

Bridgeport Jazz Festival

Bridgerport
Saturday, August 30, 2025
Now in its 5th year, the Bridgeport Jazz Festival returns to Downtown Bridgeport and is considered one of the areas for premier music performances on the McLevy Green stage. READ MORE

The Fairield International Food Fest

Fairfield
Saturday, August 30, 2025
Come to the Fairfield Theater Company to enjoy  live music & dance, interactive experiences + films across 3 stages, immersive art, henna, crafts, face painting, live mural, photo booth + Around-the-World selfie gallery and more! READ MORE

Corn Maze and Cider Donut Festival at Lyman Orchards

Middlefield
Saturday & Sunday, August 30-31, 2025
  Head over for the Ribbon Cutting Ceremony at the Corn Maze at 10 AM on August 30th. Visit the corn maze (theme still to be announced!), listen to live music, face painting, food trucks and more.  READ MORE

Bishop's Fall Festival in Guilford

Guilford
Sunday & Monday, August 30-September 1, 2025
Join Bishop's for their annual Fall Festival, running August 30 through November 1, where classic autumn fun meets Connecticut pizza pride. Enjoy apple picking, corn maze, activity area, wagon rides, cider, and more — this year, all infused with a special nod to the state’s most iconic food …stay tuned for more, this year’s Fall Festival is one you knead to experience.  READ MORE

The Connecticut Renaissance Faire

Lebanon
Opening Weekend
Sunday to Monday, August 30 - September 1, 2025
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

Goshen Fair

Goshen
Sunday & Monday, August 30-September 1, 2025
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

Madison Salute to Our Heroes

Madison
August 31 - September 1
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

Season Opening of BF Clyde's Cider Mill in Stonington

Stonington
Monday, September 1, 2025
Family-owned and operated since 1881, B.F. Clyde’s Cider Mill is a piece of living history. Every September 1st, we open our doors and sell sweet cider, hard cider, wine, cider donuts, and many local goods. READ MORE

Newtown Labor Day Parade

Newtown
Monday, September 1, 2025
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

Labor Day Concert with United States Coast Guard Band

New London
Monday, September 1, 2025
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

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About the Author

Jenny Coe
Jenny Coe is a longtime Mommy Poppins writer and contributor and full-time mom to three boys. Jenny has also been a contributor at Patch and The Reminder (Hartford Courant). Here at Mommy Poppins, Jenny writes about great things for kids to do in Connecticut and New England, affordable fun, and nature experiences (her favorite!).
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