Fall practically comes with its own playlist—apples snapping, cider pouring, leaves crunching as you walk. Throw in a pumpkin patch, and you’ve got the perfect weekend. These homes put you close to the orchards, cider stops, and all the fall fun that makes the season great. Call it the core of autumn living—ripe for the picking.
256 Main Street – East Hampton, Amagansett, NY
Just two minutes from Amber Waves Farm, this home is perfectly placed for fresh air farm escapes. Think flower fields, chickens, a farm kitchen with grab-and-go bites, and even “little farmer” classes for the kids—all open year-round for a quick visit or a full day outdoors.
Find out more about Amber Waves Farm and their classes here
322 Rose Hill Road – Southampton, Water Mill, NY
Just nine minutes from Hank’s Pumpkintown, this Water Mill home practically has fall adventure built in. Think apple and pumpkin picking, corn mazes, tractor train rides, giant slides, games, playgrounds—not to mention a market full of freshly baked pies, cider donuts, candy apples, and more.
Check out all the fall fun Hank’s Pumpkintown has to offer here
356 Warren Street – Hudson, NY
Just eleven minutes from Hopedale Farm, this Hudson home puts apple season within arm’s reach (no pun intended). Family-owned since 1916, the farm is known for its pick-your-own orchards—a timeless way to spend a crisp fall day.
Pick your own apples at Hopedale Farm here
5 Tall Oaks Road – North Wilton, CT
Just twelve minutes from Ambler Farm, this Wilton home is close to a true community gem. From pumpkin patches and farm animals to kids’ programs, picnics in the fields, and the 25th Annual Ambler Farm Day, it’s the kind of place that makes fall unforgettable.
Discover more about Ambler Farm and its programs here
153 West Main Street #TH21 – Tarrytown, NY
Twenty-two minutes from Thompson’s Cider Mill, this Tarrytown home is a short drive from a true taste of fall. On weekends, you can watch as they press fresh, old-fashioned cider, sample their blends, and even explore their small-batch artisanal hard ciders.
Explore Thompson’s Cider Mill here
82 -84 Watchung Avenue – Montclair, NJ
Twenty-two minutes from Fairfield Farms, this Montclair townhouse is close to a fall favorite with loads of family-friendly activities. Think spooky trails, hayrides, pumpkin picking, goat visits, corn mazes, big bale climbs, rope mazes, rolling tube rides, and even a pumpkin slingshot.
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