An old road over Overlook Mountain connected Tannersville with Meads and Woodstock. The approach from the north via Tannersville is less steep and is suitable for intermediate skiers. The descent from the top to the south to Meads is better considered an example of ski mountaineering than of Nordic skiing. The route is of jeep road width, but is continuously steep. This part of the route is rated expert. The trail is 7.6 miles long.

Notch, blue markers; and to the Devil's Path to Indian Head Mountain, red markers. These side trails are not suitable for skiing. At the junction of the Indian Head trail, the Old Overlook Road trail continues on the left fork with blue markers.

In Tannersville, take County Route 16 towards Platte Clove for about 6 miles. A Department sign indicates a turn-off to the south (right), on Prediger Road. The trail starts at the end of Prediger Road on red markers.

Overlook Mountain is a trail suitable for both intermediate and expert skiers. The trail first starts off with a moderately steep trail, suitable for intermediates, but becomes continuously steep, a section recommended for experts only.