Length: 2.4 miles • Elevation: 3,140 feet • Highlight: View from the fire tower
Beginning on Meads Mountain Road just north of Woodstock, the red-blazed Overlook Spur Trail takes you up to the summit of this storied mountain, which was a favorite subject of the Hudson River School painters. Along the way, you’ll pass the ruins of the Overlook Mountain House, a Catskills resort originally built in 1871. At the top, climb the recently restored fire tower, and marvel at the view — which (if the weather is clear) includes the Hudson Highlands to the south, and portions of Connecticut and Massachusetts to the east.
ALSO CHECK OUT:
Burger Hill A popular sledding site, this Rhinebeck locale features a half-mile trail that leads to an open meadow with views stretching from the Berkshires to the Catskills.
Schunemunk Mountain The highest peak in Orange County; explore the mountain via various scenic trails such as Dark Hollow, Barton Swamp, Trestle, Western Ridge, and Otterkill.
Castle Rock Carriageway Follow the blue trail markers from Lake Minnewaska for the moderately difficult, 3.5-mile climb to Castle Point. At 2,200 feet, it’s the highest point in Minnewaska State Park Preserve.