Ridge Hill's Oktoberfest event features plenty of kid-pleasing fun. Photo courtesy of Ridge Hill
Best 2025 Oktoberfest Kid-Friendly Celebrations in Westchester and the Hudson Valley
The Great Jack-o'-Lantern Blaze in Van Cortlandt Manor is a must-do Halloween event in the tri-state area. Photo courtesy of the Historic Hudson Valley
Best Halloween Events in Westchester and the Hudson Valley 2025 for Kids and Families
Kelder's Farm in Kerhonkson offers acres of pumpkins to pick, plus tons of family-friendly activities and seasonal photo-ops. Photo courtesy of the farm
Best Pumpkin Patches in Westchester and the Hudson Valley for Kids
Find spooky Halloween fun around the Hudson Valley with our guide
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The pie eating contest is just the start of the fun at the Armonk Cider and Donut Festival. Photo courtesy of the festival
Best Harvest Festivals & Pumpkin Festivals in Westchester and the Hudson Valley for Fall Fun in 2025
Join the Monster Party at Legoland's Brick-or-Treat this month. Photo courtesy of Legoland
Halloween and 20 More Top Things To Do in Westchester and the Hudson Valley with Kids October 2025, from Mommy Poppins Editors
Ridge Hill's Oktoberfest event features plenty of kid-pleasing fun. Photo courtesy of Ridge Hill
Best 2025 Oktoberfest Kid-Friendly Celebrations in Westchester and the Hudson Valley
Pick from a number of apple varieties at Hudson Valley orchards. Photo by Leslie Seaton via Flickr
Apple Picking in the Hudson Valley: Best Apple Farms and Apple Festivals
Outhouse Orchards Corn Maze. Photo by Matt Nighswander
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Apple picking is one of the family-friendly fall activities you can enjoy in the Hudson Valley with Kids. Photo courtesy of the author
Your 2-Day Itinerary for a Kid-Approved Fall Weekend in the Hudson Valley
Woodstock is the perfect fall getaway and just a two-hour drive away. Photo by Diana Kim
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Enjoy glorious views on the Walkway Over the Hudson. Photo by Fred Schaeffer/courtesy of the Walkway.
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A visit to the United States Military Academy is a lesson in history and patriotism, but also tons of fun for families.
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Kids can run, swing, slide, and even make music at Sally’s Dream Playground in Montgomery. Photo by Katherine Dhurandhar
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The Saugerties Lighthouse is a stunning getaway no matter the season.
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The Play Place in Elmsford is one of Westchester's top indoor play spaces.
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Roam the the cedar walk and gardens at Caramoor for a free, fun outing. Photo by Gabe Palacio
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Enjoy water sports at Westchester Summer Day in Mamaroneck. Photo courtesy of the camp
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Palisade Center's Climbzone features themed rock walls as high as 40 feet. Photo courtesy of Climbzone.
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The Ausable Chasm has been described as the Grand Canyon of the Adirondacks and it's one of our top 100 things to do in New York State with kids. Photo by Anna Fader
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Poughkeepsie's Gravity Vault is an indoor rock-climbing gym with classes for kids as young as 5. Photo by Kaylynn Ebner
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Mount Kisco's Grand Prix New York, a go-kart hot spot, offers birthday parties with racing, arcade play, and virtual reality.
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Kids explore the great outdoors Hudson Highlands Nature Center. Photo courtesy of the center
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At Moe's Southwestern Grill, kids eat free on Tuesdays with the purchase of an adult entree. Photo courtesy of the restaurant
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Kids under 1 are FREE hours at the Westchester Children’s Museum. Photo courtesy of the museum
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Kids can peek into the marine life in the aquariums at the Marine Education Center in Mamaroneck. Photo by Susan Miele
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Castle Fun Center in Chester has a giant inflatable park, a rock wall, laser tag, and more. Photo by Katherine Dhurandhar
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Grab a colorful treat at Harley's Sweet Shop in Woodstock. Photo courtesy of the shop
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Kids can climb the walls at the Cliffs in Valhalla. Photo courtesy of the Cliffs
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Touch the soft rabbits at the Greenburgh Nature Center's petting zoo in Scarsdale. Photo courtesy of the center
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Peekskill, NY, is a lovely riverfront community that acts an the unofficial gateway to the Hudson Valley.
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Explore what makes things fly with the Westchester Children's Museum's Wind Tunnel Design Challenge. Photo courtesy of the museum
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Romp through the woods in the beautiful Catskills. Photo by Deborah Dadlani
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Tig & Peach offers drop-in, no reservations required, open play 7 days a week.
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Friends young and old enjoy the attractions and Legoland New York, the first major theme park in the Northeast in 40 years.
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Frost Valley YMCA offers a variety of day and overnight camps for kids ages 5-14. Photo courtesy Frost Valley YMCA
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Kids love a birthday party filled with games and pizza at Chuck E. Cheese. Photo courtesy of Chuck E. Cheese
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Head to the Mid-Hudson Discovery Museum from 5-8 pm on the third Saturday of the month to explore the museum for free, Photo by the author
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Creating a baking soda volcano is a classic science experiment for kids. Photo by Sara Marentette Nighswander
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Kids can while away hours of a day with a set of watercolors and a stack of new paper for painting. Photo by Sara Marentette
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Enjoy fall festivities at Yonkers' Ridgetoberfest this weekend. Photo courtesy of Ridge Hill
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31 Summer Festivals and Fairs in 2025 in Connecticut for Families

Find big fun at Connecticut Summer Fairs and Festivals in 2025! Norwalk Seaport Association's Oyster Festival, photo by Ally Noel for Mommy Poppins.
Find big fun at Connecticut Summer Fairs and Festivals in 2025! Norwalk Seaport Association's Oyster Festival, photo by Ally Noel for Mommy Poppins.
5/16/25 - By Jennifer Coe

What a great (and inexpensive) way to spend your summer in Connecticut! Our summer calendar is packed with fun, family-oriented fairs that have rides, food, entertainment and more. Start with strawberries, celebrate with fireworks and close out the season with a Caribbean celebration! Many of these fairs are locally based, bringing the flavors of your neighborhood such as the Polish community in New Britain, oysters in Milford and yummy pizza in Bridgeport! 

Be sure to check out our Ultimate Connecticut Kids Summer Vacation Guide to keep up with new listings of summer fairs and festivals, as well as fun family events and activities. And our Guide to Free Fun Things To Do for Connecticut Kids helps plan for more epic adventures at just the right price to stretch the summer budget.

 

OUR LATEST VIDEOS

These 2025 CT Summer fairs and festivals share culture, ideas, and lots of fun! International Festival of Arts and Ideas photo by Garba360, courtesy of the festival.
These 2025 CT Summer fairs and festivals share culture, ideas, and lots of fun! International Festival of Arts and Ideas photo by Garba360, courtesy of the festival.

Summer Festivals and Fairs in Connecticut - June 2025

Torrington Strawberry Festival

Torrington
May 31, 2025
Enjoy a day of fun and, of course, delicious fresh-made strawberry shortcake and other strawberry treats. Food trucks will provide delicious food, and entertainment for the kids includes the Strawberry Festival Express Train. READ MORE

Cheshire Strawberry Festival

Cheshire
June 7-8, 2025
Enjoy mouth-watering fresh strawberry shortcake, hot dogs, hamburgers, cotton candy, and other treats at the annual celebration of this traditional New England festival. Activities will include: vendors, food, arts and crafts, games, inflatables and more. READ MORE

Little Poland Festival in New Britain

New Britain
June 8, 2025
Experience a taste of Europe in New Britain's unique Little Poland district. Enjoy live music, mascots, kids' activities, leaping folk dancers, ethnic food, arts and crafts, and shopping. READ MORE

International Festival of Arts and Ideas

New Haven
June 14 - June 28, 2025
The International Festival of Arts & Ideas is an extravaganza of performing arts, lectures, storytelling, music, and conversations that take over theaters, town green, and open spaces in New Haven. The 2025 schedule runs from June 14 through June 28, and most events are free. READ MORE

Lyman Orchards' Strawberry Fest

Middlefield
June 14, 2025
There’s no sweeter way to celebrate the start of Summer ‘25 than by joining in on all the fun at the Lyman Orchards Strawberry Festival.  It’s all happening at the Apple Barrel Farm Market and grounds on Saturday, June 14. READ MORE

Connecticut Bacon Festival in Lebanon

Lebanon
June 14 -15, 2025
It’s the 2025 Connecticut Bacon Festival taking place at the beautiful Lebanon Fairgrounds in Connecticut. This family fun event has everything bacon imaginable from food to crafts, to songs, games…… the list goes on and on. READ MORE

CT Localpalooza in Bethany

Bethany
June 15, 2025
Presented by Adventures in Music Productions, CT Localpalooza is a one day music & artfestival supporting the CT local music and art scene celebrating artistic & cultural diversity & inspire creative engagement. READ MORE

Trumbull Day (& Fireworks)

Trumbull
June 27-28, 2025
Trumbull Day is a two-day,fun-filled family event with food, vendors, carnival rides and games, children's entertainment, a main stage featuring local bands, and fireworks.  READ MORE
These Connecticut fairs and festivals are sure to light up a smile or two! Photo courtesy of Vernon’s Annual Summer Days Carnival
These Connecticut fairs and festivals are sure to light up a smile or two! Photo courtesy of Vernon’s Annual Summer Days Carnival

Summer Festivals and Fairs in Connecticut - July 2025

Annual North Stonington Fair

North Stonington
July 10-13, 2025
The North Stonington Agricultural Fair is sponsored by the North Stonington Community Grange and the North Stonington Volunteer Fire Dep't. Enjoy entertainment, food, and wholesome fun for the entire family and learn about farm life, see tractor and livestock pulls, view beautiful arts and crafts and enter some exciting competitions. READ MORE

Enfield 4th of July Town Celebration

Enfield
July 11-13, 2025
The Fourth Of July Town Celebration Committee provides the residents of Enfield CT and the surrounding communities a three-day Fourth of July Celebration at no charge, including music, parade, races, demonstrations, kid's ride's and games, with much, much more. READ MORE

Rowayton River Ramble

Norwalk
July 12, 2025
The River Ramble is a beloved Rowayton event for all ages. Enjoy live music, water rides, a petting zoo, a shopping park filled with amazing artwork, sporting events, food and wine experiences, health and fitness occasions, along with a LIVE auction. READ MORE

Norwich Carnival & Food Truck Festival

Norwich
July 12-13, 2025
The Carnival & Food Truck Train is coming to Dodd Stadium. Three days of Carnival rides and Games, Food Trucks from around New New England, music, and more. READ MORE

Pizza & Brew Fest in Bridgeport

Bridgeport
July 20, 2025
Come sample some of the best of CT's pizza and craft beers. Buy a slice from each vendor and compare! Best pizza will be awarded. READ MORE

Vernon’s Annual Summer Days Carnival

Vernon
July 23-26, 2025
Enjoy rides, games, and carnival food at the annual Vernon Summer Days Carnival. READ MORE

Lebanon Country Fair

Lebanon
July 25-27, 2025
This major agricultural fair features livestock, crafts, carnival rides, continuous entertainment, children’s games, food vendors, monster trucks, and helicopter rides.  READ MORE

Litchfield Jazz Festival

Litchfield
July 25-27, 2025
Set in the picturesque, rolling Litchfield Hills, the Litchfield Jazz Festival was established over a quarter century ago. That first line-up in 1996 would be the envy of any major festival today—Diana Krall, Christian McBride, Terence Blanchard, Russell Malone, Peter Bernstein, Ahmad Jamal, Renee Rosnes, JJ Johnson ... If you remember this or any of the wonderful festivals that followed, you won’t want to miss Litchfield Jazz Fest 2025. READ MORE

Rose Arts Festival in Norwich

Norwich
July 27-28, 2025
New England's largest free music and art festival, Rose Arts is not to be missed. Featuring family-friendly interactive activities, exciting art installations, and more than 75 performances spanning day and evening programs, this is a wonderful way to spend the day.  READ MORE
With food, rides, and more, these 2025 fairs and festivals have something for everyone! Photo courtesy of the Milford Oyster Festival
With food, rides, and more, these 2025 fairs and festivals have something for everyone! Photo courtesy of the Milford Oyster Festival

Summer Festivals and Fairs in Connecticut - August 2025

Taste of the Caribbean and Jerk Festival in Hartford

Hartford
August 2, 2025
Authentic Caribbean cuisine, cool island beverages, island rhythms, and spectacular costumes and dance bring a festive Caribbean atmosphere to the riverfront, during a free, day-long, family-friendly festival.  READ MORE

Stonington Village Fair

Stonington
August 2, 2025
With the assistance of more than 100 volunteers, this popular community event brings together local and tourist alike, for a fun-filled day of games, music, food, and crafts. Entry is free for all—check out some of the highlights of the event below! READ MORE

Podunk Bluegrass Music Festival in Goshen

Goshen
August 7-10, 2025
The annual bluegrass festival features local, regional, and national bluegrass, bringing together the finest in bluegrass music each year. Enjoy a day of family activities, camping, and vendors.  READ MORE

Riverfront Dragon Boat & Asian Festival in Hartford

Hartford
Aug. 16, 2025
Celebrate Asian and Pacific Island cultures through traditional music and dance, hands-on art activities, food, and martial arts. Dragon boat races are back this year. Come cheer on your favorite team! READ MORE

The Brooklyn Fair

Brooklyn
Aug. 21-14, 2025
Make memories at one of the oldest continuously run fairs in the United States. Fireworks, baking contests, truck pull, racing pigs, animal competitions, and an entire kids' stage all await.  READ MORE

Woodstock Fair

Woodstock
Aug 28 - Sept. 1, 2025
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
Aug 29 - Sept 1, 2025
All weekend long, there will be rides, concessions, petting zoo, children's activities, agricultural contests, entertainment, and more. READ MORE

Goshen Fair

Goshen
Aug 30 - Sept. 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
Hold on to Summer 2025 right into September at these fairs and festivals! Photo courtesy of the Garlic Festival at Old Mistick Village
Hold on to Summer 2025 right into September at these fairs and festivals! Photo courtesy of the Garlic Festival at Old Mistick Village

Summer Festivals and Fairs in Connecticut - September 2025

Norwalk Seaport Association's Oyster Festival

Norwalk
Sept. 5-7, 2025
The beloved annual Oyster Festival features live music from dozens of bands on multiple stages, as well as festival entertainment and attraction for the whole family.  READ MORE

St Peter’s Annual Apple Festival

Monroe
Sept. 6-7, 2025
St Peter’s Annual Apple Festival is a community tradition held on the historical Monroe Green where craft vendors from around New England sell everything from doll clothes to jewelry to woodcrafts. There are games for kids, lots of food and baked goods, and, of course, plenty of apples. READ MORE

Connecticut Potato & Corn Festival in Middlefield

Middlefield
Sept. 13-14, 2025
Join in celebrating two of the tastiest foods in the world - potatoes and corn. Food vendors will be using these two ingredients to make many mouth watering menu items. READ MORE

Kefi Greek Festival in Norwalk

Norwalk
Sept, 14-16, 2025
Looking for an unforgettable weekend the whole family will love? Join the KEFI Greek Festival—a celebration bursting with flavor, culture, and fun for kids of all ages. Get ready for thrilling rides, kid-friendly games, and live music that’ll get everyone dancing.  READ MORE

Garlic Festival at Old Mistick Village

Mystic
Sept. 20-21, 2025
The  Annual Mistick Garlic Festival with over 40 vendors, food for the whole family and lots of fun. An amazing variety of garlic will be for sale from local farmers. You can also buy local honey and other tasty treats.  READ MORE

Places featured in this article:

Lebanon Fairgrounds
Hartford Healthcare Amphitheater
Historic Downtown Norwich

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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