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Sep 25, 2025  |  
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NextImg:Apple watch: Pair a you-pick-it outing with an overnight break

There’s no better autumn activity than apple picking at one of the many pick-your-own farms around the five boroughs. After all, there are endless hayrides to hop on, corn mazes to explore, picnics to be had and cider donuts to snack on, once you’ve collected bushels of your favorite variety.

To make it a true staycation, book a nearby hotel and make a getaway out of it — here’s a few to pick from.

Collect from over 40 varieties of apples at Wilkens Fruit & Fir Farm, Yorktown Heights, NY. Instagram/Wilkens Farm

In Westchester County, you can pick-your-own and sleep in a former convent. First, head to the family-run Wilkens Fruit & Fir Farm in Yorktown Heights, NY, where the focus is on apple picking — there are over 40 varieties here — plus freshly baked pies ready for purchase, a corn maze to explore, a cider mill producing pressed apple cider and seasonal activities, like pumpkin picking, for kids of all ages.

Drive for 20 minutes from here and you’ll arrive at the Abbey Inn & Spa in Peekskill, NY. The restored convent and chapel, which dates back to 1902, has breathtaking views of the Hudson River, and the whole family can enjoy the serene walks around the property, cool evenings at the firepit and delicious farm-to-table dishes at Apropros, the resort’s on-site restaurant.

Prices from $549 per night.

Go back in time to the Reclaimed Hotel in Red Hook, NY, which features vinyl records, vintage décor and a relaxing vibe. Katie Naclerio

In Dutchess County, an outing at Greig Farm in Red Hook in the Hudson Valley might start with apple picking, but it will most definitely end with lunch in the market, a walk through the SoHu craft market, featuring works by local artists, or even a chance to feed the super cute pygmy goats with some alfalfa pellets. Be sure to bring a few quarters if you’d like to feed them from your hand.

Go a little over a mile down the road and you’ll arrive at the Reclaimed Motel, an eight-room throwback to the iconic motor lodge. The motel boasts gorgeous views of the Catskills, vinyl records to set the mood and hand-selected vintage décor that will make you feel like you’ve walked into the most fabulous of thrift shops.

Prices from $310 per night.

Wander 200 acres of Masker Farm in Warwick, NY. Handout

You can drive right up to the apple trees at the 200-acre Masker Orchards in Warwick, NY, where seven types of apples are available for picking.

There’s no admission fee to spend the day at the farm, although you’re required to purchase one bag of apples ($39.95) per carload.

While you’re in town, your kids will delight in an overnight at Legoland.

Have a blast at Legoland Hotel in nearby Goshen. Courtesy of LEGOLAND® New York Resort

Located in Goshen, just 20 minutes away from the farm, the 250-room hotel is a quick walk to the front gate of Legoland New York. With themed rooms such as Pirates, Lego Friends, Kingdom and Ninjago, an indoor playspace and daily scavenger hunts, your brick-making kids are sure to have a blast.

Prices from $299 per night.

Let off steam at Bishop’s Orchard in Guilford, Conn. Connecticut Office of Statewide Marketing and Tourism

Bishop’s Orchard in Guilford, Conn., is a local favorite boasting over 20 varieties of apples, and is beloved for its weekend tractor wagon rides around the orchard.

In keeping with Connecticut’s pizza pride, this year the orchard is debuting a 3.5-acre New Haven-pizza-themed corn maze.

There’s also bounce pads, a megaslide and a market on-site so you can bring all those yummy apple cider donuts back to the city with you.

Relaxing by the beach firepit at Madison Beach Hotel on the Long Island Sound. Courtesy of Madison Beach Hotel

Venture 8 miles to the stylish Madison Beach Hotel and book one of the 34 rooms, each of which overlooks a private beach on the Long Island Sound.

There’s plenty to do here if you want to hop on a bike, jump in a kayak or enjoy the cute shops along this beach town’s main drag, located just a mile away from the hotel.

Prices from $376 per night.