One of the best things about living in Greenwich? A picture-perfect New England fall day is less than an hour away.
There’s something about fall in Greenwich that makes you want to get outside and enjoy every bit of the season. The crisp air, changing leaves, farm stands, cider donuts—and, of course, apple picking. While you won’t find sprawling apple orchards right here in Greenwich, you don’t have to travel far to turn an ordinary fall afternoon into a quintessential New England experience. Some of the area’s best pick-your-own orchards, cider mills, farm markets, and pumpkin patches are an easy drive away, making apple picking one of my favorite fall day trips from Greenwich.
The good news is that Greenwich is hemmed in by orchards on two sides. Head north into Westchester and Putnam and you're in rolling farm country within forty minutes. Head northeast into inland Fairfield County and you get the old Connecticut cider mills, the ones with the press running behind a plate-glass window. Both are day trips. Neither requires a hotel.
Below, the trips are sorted by how far you're willing to drive.
Under 45 minutes: The Westchester run
North Salem is the sweet spot. Two of the area's best-known orchards sit within a few minutes of each other on the same stretch of back road, which means you can hedge: if one lot is full, the other is right there.
Harvest Moon Farm & Orchard — North Salem, NY
~35 min · 130 Hardscrabble Road
The polished one. Harvest Moon offers more than thirty apple varieties for picking, with a farm store open daily and apple picking available via ticket during fall festival weekends. The festival weekends bring live music, hayrides, food vendors, and a genuinely excellent cider donut. Adults get Hardscrabble Cider, the on-site hard cider bar — which is why this one skews a little more date-day than the others. Buy tickets in advance; the weekend capacity is real.
Outhouse Orchards — North Salem, NY
~35 min · Hardscrabble Road, just down from Harvest Moon
Less polish, more field. Twelve-plus varieties, pumpkin picking, hayrides, a corn maze, and a fall festival that runs from late summer into early November. The barn does warm cider donuts, pie, and fresh cider. If Harvest Moon feels like an event, Outhouse feels like an afternoon.
Stuart's Fruit Farm — Granite Springs, NY
~45 min · 62 Granite Springs Road
The sentimental pick. Family-operated since the 1820s and one of the oldest working farms in Westchester, Stuart's does apples, pumpkins, weekend hayrides, and a farm stand full of cider donuts and pies made on site. Two things worth knowing before you leave the house: there's no orchard entry fee and parking is free, but the farm takes cash or check only. Pack a picnic and eat it in the orchard.
Wilkens Fruit & Fir Farm — Yorktown Heights, NY
~50 min · 1335 White Hill Road
The one with the longest runway. Wilkens opens in August and its pick-your-own apple season stretches from early September into mid-November, across Gala, McIntosh, Baldwin, Golden Delicious, Crispin, and Fuji. There's a corn maze, an ice cream shop, and a bakery turning out cider donuts, strudel sticks, pies, and loaf breads. Come back in December and you can cut a Christmas tree in the same spot — the "Fir" in the name isn't decorative.
45 to 60 minutes: The Connecticut cider mills
This is the other flavor of the day, and for some people it's the better one. Less festival, more agriculture.
Beardsley's Cider Mill & Orchard — Shelton, CT
~50 min · 278 Leavenworth Road (Route 110), White Hills
If you only do one, make it this one. The Beardsley family has farmed the land since 1849, and the mill presses pure, untreated cider you can watch being made. The orchard runs to roughly fourteen thousand dwarf trees that top out around ten or twelve feet, which is the whole trick: a five-year-old can reach the fruit without a pole or a parent.
Two logistics that catch people out. Pick-your-own is weekends only, roughly 10 a.m. to 4:45 p.m., September through October, weather permitting — but the farm store is open daily, 10 a.m. to 5:30 p.m., and stays open all the way to Christmas Eve. And no dogs in the orchard. Call the farm's phone message or check their social feed for the day's varieties before you commit to the drive.
The insider move: come on a weekend after 11 a.m. and you can have a fermenting container filled with fresh-pressed untreated cider to take home and turn into your own hard cider. They also bottle their own.
Silverman's Farm — Easton, CT
~45 min · 451 Sport Hill Road
The kid-maximizing option. Alongside the orchard there's a five-acre animal park, a pumpkin patch, greenhouses, a market with fresh-baked pies, local honey, sweet cider and apple dumplings, and Christmas trees come December. Picking runs roughly 9 a.m. to 4:30 p.m. in season, with the market and animal farm open seven days a week from 9. The tractor ride up to the orchard is half the appeal if you're under eight.
One caveat: weekend afternoons here are the busiest stretch of the whole region. A weekday morning is a completely different farm.
Blue Jay Orchards — Bethel, CT
~55 min · 125 Plumtrees Road
A 122-acre orchard in northern Fairfield County with more than eight thousand producing trees and twenty-plus varieties. Picking is a weekend affair, generally 10 a.m. to 5 p.m. from early September, with wagon rides and a pumpkin patch that opens up in late September. It's the least crowded of the closer Connecticut options, which counts for a lot on Columbus Day weekend.
Ninety minutes-plus: The full-day version
Worth it once a season, ideally on a weekday, ideally with lunch built into the plan.
Lyman Orchards — Middlefield, CT
~1 hr 30 min · 32 Reeds Gap Road
The heavyweight. Lyman's has been farmed by the same family for more than 280 years, its pick-your-own fields spread across roughly 200 acres overlooking the Connecticut River Valley, and it's been voted the state's best pick-your-own farm. Apple season here spans a long arc — mid-August into mid-November in a normal year — and overlaps peaches and pears at the front end, so an early trip gets you three fruits in one bag.
Two current notes for 2026: the season opened early after a warm spring, and the farm has said it expects apples to wind down around late October rather than running into November. Picking has also moved deeper into the rows, meaning more walking. There's a 24-hour picking hotline — 860-349-6015 — and it's genuinely worth calling before a 90-minute drive.
Rogers Orchards — Southington, CT
~1 hr 30 min · Two locations: Long Bottom Road and Meriden-Waterbury Turnpike
Eighth-generation, ninety acres, twenty-plus varieties. Pick-your-own opens around Labor Day with McIntosh and runs to late October, when Golden Delicious, EverCrisp and Pink Lady come in — and it's Friday through Sunday only, at both farms, weather permitting. The farm store is the real draw for a lot of people: apples by the bushel, cider, donuts, pies, and their own jams and jellies.
--
Of course, the only problem with apple picking is that, somehow, you always come home with more apples than you know what to do with! Now that you've picked them, what are you going to make with them? Here are three of my favorite apple recipes –– because apple picking is fun, but eating what you make with them can be even better. If you try any of these recipes, I'd love to hear from you –– reach out and let me know how they turned out!
