7 Connecticut Towns for Fall Family Fun Last Updated: August 2023

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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 safety-friendly 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. And be sure to check with each location before venturing out, as hours may change.


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.

In Mystic Seaport Museum, you can stroll through the gardens of a historic New England seafaring village. Continue your historical tour of Mystic by visiting the last steam-powered cider mill in the United States, B.F. Clyde’s was designated a National Mechanical Engineering Landmark in 1994 and has been squeezing out cider since 1881. Then for some daring fun, take a spooky Seaside Shadows Haunted History Tour or climb above the trees at Tree Trails in Mystic. Just be sure to make a reservation!

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. 

Experience the fresh air and quintessential New England charm in nearby Cornwall with a trip over the Cornwall 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 leaf peeping... on a horse! Take the gang to Lee's Riding Stable for all-levels horseback riding and of course, stunning views of foliage!


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, ideal for picking your pumpkin right off the vine. Gold Rush Farm is perfect for finding friendly horses and trail rides galore!


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. Experience the views by bike or boat at Connecticut Shoreline Bike/Boat Tour. You can continue your autumn adventuring 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 “truly 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 with a waterfall-view meal at Millwright's or Sunday brunch at Abigail's Grille & Wine Bar.

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 attend fun programs and events — sometimes even spooky Halloween activities!

Want more ideas for not-so-scary Halloween fun? Check out these kid-friendly outings!