CT Fall Day Trips Guide: Orchards, Festivals, and Family Getaways 2025

Fall fairs & festivals, apple picking at orchards, pumpkin patches, train rides, haunted houses, and corn mazes are all in full swing.

We’ve rounded up some of the best autumn activities for families in Connecticut, from festivals, apple picking, farm visits, and weekend getaways to leaf peep or get lost in a corn maze!

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Watch the Macy's Thanksgiving Parade. Photo courtesy of the Macy's Thanksgiving Day Parade
Thanksgiving, Pumpkin Destruction Day, and More Holidays & Activities for November 2025
From pickles to freckles to Monopoly - plus Thanksgiving!
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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
These traditional Bavarian festivals are fun for both kids and adults.
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Rockefeller State Park Preserve offers a rainbow of fall foliage to take in during the autumn.
Spectacular 2025 Fall Foliage Viewing Spots in Westchester and the Hudson Valley
These are our favorite spots to see the season's colors.
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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
Head to these nearby farms to pick the perfect pumpkin.
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Twilight Village takes over Philipsburg Manor on select nights during the spooky season. Photo by author
Best Sleepy Hollow Attractions for a Spooky Family Day Trip
Sleepy Hollow's legends and lore really come to life during the Halloween season!
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The witchy sisters from Hocus Pocus 2 are back! Photo courtesy of Disney Enterprises, Inc. © 2022 Disney Enterprises, Inc. All Rights Reserved.
31 Best Kids' Halloween Movies with Not-so-Scary Thrills and Chills
Queue up some mild Halloween frights for family movie night.
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