The Highlands Trail starts at the bottom of Dock Hill Road at the CSX RR crossing by the Hudson River in Cornwall, NY.  Parking in this area is available to Cornwall residents only and is strictly enforced. Follow the blazes uphill on Dock Hill Road .3 miles, turn at first left on Dock Hill Ave. for .1 mile, and come to Route 218 (Bayview Ave). The trailhead is across Bayview Ave from the intersection.

At .7 miles, reach a hiker parking lot, where parking is available. Follow the trail along fields, up Storm King Mountain along a stream, and past some viewpoints to a junction with the yellow-blazed Stillman Trail at 1.4 miles. Proceed along the co-aligned Stillman (yellow) and Highlands Trails over Storm King Mountain, then back down the mountain to a driveway that leads out to a left turn on Mountain Road at 4.4 miles.  

After a short distance, turn left off of Mountain Road and pass through a tunnel under US 9W. Walk to the Black Rock Forest parking lot on Reservoir Road at 4.8 miles. Turn left uphill across the street from the parking area, still on the co-aligned Stillman and Highlands Trails. Pass the Upper Reservoir, and climb over steep Mount Misery and Black Rock. 

At 9.1 miles, reach a junction where the Stillman Trail and the northbound Compartment Trail (blue) go off to the right, and the co-aligned southbound Compartment Trail and Highlands Trail continue straight ahead. In another 0.6 miles, the Compartment Trail ends at a ‘Y’ junction with Jim’s Pond Road. The Arthur Trail (yellow) begins here and follows Jim’s Pond Road to the left.

Turn left onto Jim’s Pond Road. Stay on the road when the yellow blazes leave the road to the left. After another 0.1 mile (9.6 miles from the start), turn right following the co-aligned Scenic (white) and Highlands Trails. Continue mostly downhill, passing a waterfall and shortly reaching Old Mineral Springs Road. Bear right on Old Mineral Springs Road and follow it about 500 feet down to Old Mineral Springs Road at 11.7 miles. 

Turn left on Old Mineral Springs Road and follow it for .3 miles out to Mineral Springs Road. Bear left on Mineral Springs Road and follow it for 1.2 miles to Trout Brook Road. Turn right on Trout Brook Road and follow it .8 miles to Route 32. Turn left on Route 32 and follow it .7 miles to where the Long Path crosses Route. 32 just before the overhead RR trestle at 14.7 miles. Turn right on the Long Path and follow it for 2.6 miles up Schunemunk Mountain, reaching the junction with the yellow-blazed Jessup Trail at 17.3 miles. Turn left at the junction. 

Follow the co-aligned Jessup, Highlands Trail, and Long Path for 3.7 miles along and down the ridge of Schunemunk Mountain to the closed portion of Seven Springs Road at Gonzaga Park, where parking is available at 21 miles.

Follow the co-aligned Highlands Trail and Long Path .2 miles down to a gate at Mountain Road. Cross Mountain Road and continue on Seven Springs Road for .4 miles, turning right off the road in a residential area. Proceed through the woods and up and over a ridge on the co-aligned Highlands Trail / Long Path, cross NY 208, and follow the shore of Orange-Rockland Lake to Museum Village Road. Turn left on Museum Village Road and follow it across NY 17. Turn left, reaching a commuter parking lot at 22.3 miles.

Turn sharply right onto the Orange Heritage Trail, formerly the Erie Railroad mainline, and proceed for a mile, crossing back under NY 17. Turn right off the Orange Heritage Trail onto the Highlands Trail (the Long Path continues straight) after a small cemetery on your right and just before a bridge, and go down the embankment to the road. Make a left under the bridge onto Craigville Road (County 51), following it to NY 17M at 25 miles. After a quick jog across 17M, turn right onto Lazy Hill Road, an abandoned, formerly paved road, and enter Goose Pond Mountain State Park. Turn left off Lazy Hill Road in 1.7 miles and follow a narrow trail out to Bull Mill Road at 28.5 miles. Cross Bull Mill Road, go over a hill with a view of Sugarloaf Mountain, and come out to a trail parking lot at 29.5 miles.

***A teal diamond with a black center-blazed trail continues for .5 miles on Lazy Hill Road to limited trail parking on Laroe Road.