This area is called 'Smilin' Thru' and reportedly inspired the 1920s song composed by Arthur Penn, who stayed on the island. Walkers should be prepared for steep slopes and some tricky footing. The trail starts on Lakeside Drive near the intersection with Cooneymus Road, and heads west along the shore of Fresh Pond. This trail links to Rodman's Hollow. Recommended: take this trail to Rodman's then south to Black Rock.