There are several trails winding through the forest covering Prospect Hill. These trail winds through some mature hardwood forest, mixed conifer and hardwood forest, and Hemlock stands. The main trail can be entered by the guard rail behind Prospect Hall. This path winds up the hill in front of a Hemlock and Pine stand and then curves around where the trail diverges. At the point where the trail sharply turns go right to the field behind Mandelle Hall. If you bear left and stay on the main trail you will shortly encounter another split in the trail. Bear right here to stay on the main loop and continue your ascent of Prospect Hill or bear left for a trail that parallels the top of the Hemlock stand. The main loop will take you to the crest of Prospect Hill and though some grassy/herbaceous openings and past one of the two town water supply tanks. On either side of the water tank are areas of blowdown (trees toppled during windstorm). This trail and the trail parallel to the Hemlock stand exit in the opening by the Ham Hall parking lot.