The historic Bear Mountain Bridge Toll House marks the trailhead for the Camp Smith Trail, a 2.5-mile hike that overlaps with the Appalachian Trail for a bit as it crosses the bridge and leads to the stunning vista of Anthony’s Nose at 900-foot elevation at the South Gate of the Hudson Highlands.

The Trail is moderately difficult, involving a steep staircase-like ascent (for about .6 miles), followed by a relatively flat stretch for .75 miles, and culminating at what you might call Anthony’s forehead, a gorgeous picnic-worthy rocky overlook with a spectacular view of the beautiful bridge below.

The bridge dates back to 1924, when it was opened as the first to span the Hudson between Albany and New York City. It was privately owned, with the slate-roofed Tudor style toll house erected to collect passage fees.

By 1940, the bridge and road were sold to the state and the structure was left vacant. The restored building, open June to October on weekends and holidays, now serves as an information and welcome center with local history displays. Both the bridge and the house are on the National Register of Historic Places.

As far as the Anthony this rock feature is named after, that’s up for grabs. Records were found with this name dating back to 1697. Washington Irving attributes the namesake to Anthony Van Corlaer, a trumpeter of New Amsterdam; another tradition claims Anthony de Hooges, a local church deacon with a notable nose.

For more about the starting point at the Toll House click here.