Kickstart your adventure with a hearty breakfast at the Kimball Terrace Inn, where you can enjoy local delicacies and freshly brewed coffee with stunning views.
Set off to Kaaterskill Falls for a rewarding hike of around 1.5 miles to witness the stunning beauty of one of New York's tallest waterfalls surrounded by picturesque fall foliage.
Drive from the inn towards Kaaterskill Falls via NY-212 W to NY-32 N.
After your hike, enjoy a delicious lunch at The Catskill Mountain Pizza, renowned for its flavor-packed artisan pizzas alongside refreshing local craft beers.
Drive back from the falls on NY-32 S to the pizza place.
Next, drive to the Giant Ledge trailhead, where a moderate 3-mile hike rewards you with breathtaking views and several beautiful ledges and waterfalls along the way.
Wrap up the afternoon with a delightful wine tasting at Whitecliff Vineyard, where you can sample exquisite local wines with the beautiful backdrop of vineyards and mountains.
Quick drive from Shadowland Stages to the vineyard.
Indulge in a relaxing dinner at The Bear Cafe, featuring farm-to-table dishes and a great selection of wines, all within an inviting ambiance overlooking the scenic river.
End your day with a charming stroll through Woodstock's artistic streets, exploring local galleries and shops, and perhaps picking up a souvenir or two.
Easily walk around the town center from the restaurant.