Dolan Orchards

Cheap prices, friendly employees, beautiful views and plenty of places nearby to visit make this a home run. For these reasons and more, picking apples here has been a family tradition for the past 20 years, and will continue to be as long as Dolan’s exists. They even let you use the picking poles for free, so you can reach apples higher in the tree, while most other orchards charge a fee (or no longer allow them). There’s also free parking and free bushel bags, saving you even more.
After driving up via Route 208 (passing many quaint towns in the process) you can make a great fall day-​trip out of apple picking, a hike at Minnewaska State Park, and a nice coffee stop in the relaxed, welcoming town of New Paltz before heading home via 87 (the highway which passes through New Paltz and can be taken directly to NYC via the Tappan Zee Bridge).