Fall Activities for Grandkids: Apple Picking & Farm Visits in Fairfield County & Westchester

Fall is the best season for grandparent-grandkid outings in Fairfield County and Westchester. Apple picking, pumpkin patches, cider doughnuts, and farm animals — these are the activities that stay in grandkids’ memories for years, and the region has some of the finest farm destinations in the Northeast.

Here’s the complete guide to fall farm visits and seasonal activities across both regions.

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Apple Picking & Orchards

Silverman’s Farm — Easton, CT

4.5 ★ | 697 reviews | Fairfield County

One of Fairfield County’s most beloved farms — operating since 1915. Pick-your-own apples, a farm market with cider and doughnuts, and farm animals including a petting area. The apple orchard is well-maintained and accessible; most rows are flat enough for grandparents with limited mobility. Peak season: September through October. Arrives early on weekends; the lot fills by 10 AM in peak season.

Silverman’s Farm | 451 Sport Hill Rd, Easton, CT

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Blue Jay Orchards — Bethel, CT

4.5 ★ | 506 reviews | Fairfield County

A 140-acre orchard in Bethel with pick-your-own apples, a farm store, fresh-pressed cider, and cider doughnuts. The orchard terrain is hillier than Silverman’s, which makes it more of a hiking experience — grandkids tend to love exploring the rows, grandparents with mobility concerns should plan for some uneven ground. Also has pumpkins in October.

Blue Jay Orchards | 125 Plumtrees Rd, Bethel, CT

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Apple Farm — White Plains, NY

4.3 ★ | 747 reviews | Westchester

A working farm right in White Plains — genuinely unusual for this area. Pick-your-own apples in season (typically September through October), farm animals, and a market with local produce. Worth timing a fall visit around if you’re already in Westchester. Check their website for seasonal availability before going.

Apple Farm | White Plains, NY

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Outhouse Orchards — North Salem, NY

4.1 ★ | 618 reviews | Westchester (Northern)

A North Salem orchard with pick-your-own apples and a farm store. In the northern part of Westchester — a longer drive from White Plains or Yonkers, but worth it if you’re in the area or looking for a more rural feel. September and October are the peak months.

Outhouse Orchards | North Salem, NY

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Hemlock Hill Farm — Cortlandt Manor, NY

4.7 ★ | 240 reviews | Westchester (Northern)

A well-reviewed family farm in Cortlandt Manor with seasonal produce, farm animals, and a warm atmosphere. Smaller and more intimate than the larger pick-your-own operations.

Hemlock Hill Farm | Cortlandt Manor, NY

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Pumpkin Patches & Fall Farms

Jones Family Farms — Shelton, CT

4.3 ★ | 502 reviews | Fairfield County

One of the most complete farm experiences in Connecticut — pick-your-own pumpkins, apples, and Christmas trees (seasonal), a farm store, and a barn complex with fall activities. The pumpkin patch in October is a reliable family event.

Jones Family Farms | 606 Walnut Tree Hill Rd, Shelton, CT

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Blue Hill at Stone Barns — Tarrytown, NY

4.7 ★ | 1,396 reviews | Westchester

The farm walk at Stone Barns is spectacular in fall — the kitchen gardens are in full harvest mode, the animals are visible, and the cafe has seasonal dishes using farm produce. Even without a restaurant reservation, the farm itself is free to walk and is one of the most beautiful farm settings in the Northeast in October.

Blue Hill at Stone Barns | 630 Bedford Rd, Tarrytown, NY

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Special Fall Events

The Great Jack O’Lantern Blaze — Croton-on-Hudson, NY

4.6 ★ | 1,913 reviews | Westchester

An annual nighttime event at Van Cortlandt Manor in Croton-on-Hudson: 7,000+ hand-carved illuminated jack-o’-lanterns arranged in elaborate displays. One of the most celebrated fall events in the Hudson Valley — grandkids remember it for years. Runs September through November; sells out weeks in advance. Evening entry only; book tickets online as soon as they go on sale.

The Great Jack O’Lantern Blaze | Van Cortlandt Manor, Croton-on-Hudson, NY

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Practical Notes

Peak season: Mid-September through late October. Apples peak in September; pumpkins peak in October.

Weekends book fast: Silverman’s Farm and Blue Jay Orchards are both crowded on October weekends. Arrive by 9:30 AM for a pleasant experience; arriving after noon on a fall Saturday is a different, more crowded visit.

What to bring: Bags (most farms provide picking bags), cash (some farm stands are cash only), and layers — it’s often warmer in the sun than it looks.

The Blaze: The Jack O’Lantern Blaze is the can’t-miss fall event for grandkids 4 and up. Book the moment tickets go on sale — they sell out.

Browse all farm and seasonal venues at grandkidsguide.com/fairfield-county-ct and grandkidsguide.com/westchester-ny.