7 Connecticut Towns for Fall Family Fun Last Updated 10/19

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From apple picking to leaf peeping, fall in Connecticut is made for family fun!  The perfect fall weekend is a mixture of quality time with the family, festivals, farms, and tons of fresh air. Connecticut has enough Fall fun to fill up an entire weekend and then some. From cider in Mystic to the farms of Easton, every corner of the Nutmeg State exudes autumnal charm just begging to be explored. Make sure to check out Mommy Poppins for more fun things to do in Connecticut this fall


Cider: Check! Cider Donuts: Check! History and yummy eats: Check! And check! We love visiting Mystic any season, but it really sparkles in the fall. The contrast of foliage against the water is simply stunning. Take in the views of the water during a sail aboard Breck Marshall, or paddle down the Mystic River in a kayak or SUP from Paddle Mystic. Perhaps the most spooky event of all is to watch “witches” float down the Mystic River at this year’s Witch Paddle

In Mystic Seaport Museum, you can stroll through the gardens of a historic New England seafaring village. During Columbus Day weekend, the village hosts Chowder Days, the perfect activity to warm up on a crisp fall day. Continue your historical tour of Mystic by visiting the last steam-powered cider mill in the U.S. B.F. Clyde’s was designated a National Mechanical Engineering Landmark in 1994 and has been squeezing out cider since 1881. Your family can check out a demonstration and learn all about the history of this place, or just grab a donut and cider slushy to enjoy while taking in the views. 

Sharon & Cornwall

Litchfield may be one of Connecticut’s largest counties in size, but I am pretty sure there are more cows, sheep, and chickens than actual people. Around 25 towns dot the Litchfield countryside, and each one of them offers sweeping views of the foliage. 

To take it all in, take a ride on Ellsworth Hill Orchard & Berry Farm’s Hayride in Sharon. Explore the farm's corn maze, pick your own pumpkins, gourds, and apples, sip on hot cider, and more. They have a small model train collection that any tiny train enthusiast will delight in. 

Experience the fresh air and quintessential New England charm in nearby Cornwall with a trip over the Corwall Covered Bridge on an electric bike. Drivers need to be 18 or over, but kids can ride along on a cargo bike. Enjoy a family ride down the Housatonic and enjoy the changing flora and fauna.   

Round out your perfect family fall weekend by celebrating all things autumn at the Mohawk Mountain Fall Festival with local artisans, food trucks, hayrides, pumpkin painting, and live music. 


Easton & Redding

There are more than twenty working farms located around Easton. Thanks to some pretty forward thinking by its residents, over one third of the land of Easton will be forever preserved—and fall is definitely its time to shine. Once you hop off the Merritt Parkway and turn down Sport Hill Road, you are magically transported to a pastoral paradise. On weekends, you will find cars lining up for Silverman’s Farm. Easton’s largest farm is also its most popular. Families have been making a trip to Silverman’s part of their fall tradition for decades. If you keep driving past Silverman’s, you will find Sport Hill Farm. A leader in sustainable farming in Fairfield County, Sport Hill is definitely worth a stop. With quirky events and a whole brood of chickens begging to be fed (not to mention a farm stand packed with fresh produce), it will quickly become a family favorite. 

You can continue your farm tour into Redding. Warrups Farm has been a family favorite for years. It provides a low-key alternative to some of Fairfield County’s more bustling farms. You can hop on a tractor, ride out to the fields and pick your pumpkin right off the vine.  New Pond Farm’s Annual Harvest Festival will offer your family a chance to spin fleece, churn butter, and savor autumnal delights.  


Foodie families will delight in a trip to the coastal town of Guilford. One hundred and twenty-five trees line Guilford’s historic Town Green, making it the perfect place to take in some Fall color... and chowder. The Guilford Green sets the perfect stage for a variety of festivals throughout the year and the Chowder Challenge is definitely the highlight of the season. You can continue munching your way down the street right to Bishop’s Orchards. With 110 acres of apples alone, Bishop's is the epicenter of fall family fun in Guilford. With an ice cream stand, corn maze, pumpkin patch, and a packed “pick-your-own” calendar at the farm, you can easily spend an entire day there. 

No trip to Guilford would be complete without a stop at The Place, a “ruly unusual outdoor seafood restaurant. This unforgettable dining experience is only open on weekends through October. Diners can pull up a tree stump to a bright-red communal table and enjoy clams, lobsters, chicken breast, and corn prepared on a crackling wood fire. 

New England is known for its quirky traditions, and Guilford doesn’t disappoint. The Technicolor turkeys at Gozzi’s Turkey Farm have been delighting visitors for about 50 years. Bring your camera and snap some pics of these Instagramable birds.  Starting in November, visitors can stop by the farm any day to check out turkeys in every color of the rainbow. 


Nestled into the northern edge of the Farmington Valley you will find the town of Simsbury, filled with farms, historic houses, and miles of hiking trails through some of the most beautiful fall foliage in the state. Hike to the top of Talcott Mountain State Park to visit the historic castle-like Heublein Tower and take in the views. Reward yourself by tasting your way through the Spooktacular Chili Challenge, featuring local vendors, cider samples, and even some trick-or-treating! 

No visit to the valley would be complete without a stop by Flamig Farm, home of the backwards EGGS sign (make sure you ask them how it came to be!) You can feed the goats, take a trip on a tractor, ride on a pony, or take a spooky trip on their Halloweeen Hayride. (Yes, there are three “e’s” for a reason. Make sure to ask them about that too!)