Alligator Hill Advanced Loop

This is the 4.6-mile Alligator Hill circuit from Stocking Road, climbing through beech-maple forest to the Islands Lookout bench above Lake Michigan and the Manitou Islands. Allow about 2.75 hours with a stop at the view. The hiking grade is moderate; “advanced” describes the winter ski rating. Choose this one for a longer wooded walk with several real climbs and one standout lake view.

Walk the short access from the gravel lot to post 1, then follow the loop to post 5. Take the 2.3-mile Advanced Trail to post 4, continue by posts 3 and 2 at Islands Lookout, and return to post 1 on the north leg. The 4.6 miles include the short access to and from the lot. The 2.3-mile label is just the southern Advanced Trail segment. Keep the route map handy where Easy, Intermediate and Advanced paths meet. The Big Glen Lookout is a separate spur; adding it brings the outing to about 6.2 miles.

The southern leg has several steep slopes and water-bar steps roughly six inches high. The tread is unpaved, and the paths are also used by equestrians. The trail system is designated for cross-country skiing from December 1 through March 31. Pets are not allowed on the trails during that period; otherwise, keep them on a leash no longer than six feet. Mountain bikes are not allowed.

All three loops reach the bench at Islands Lookout, which faces Lake Michigan and the Manitou Islands. Sleeping Bear Point and, on clear days, sometimes South Fox Island or freighters in Manitou Passage can also be visible. Frame the water from the bench with the forested slope and pale shoreline below; this is the trail’s best place to pause.

From the Dune Climb, the ridge’s profile looks like an alligator’s snout. Glaciers shaped Big and Little Glen Lakes, and an older Lake Michigan shoreline cut the bluffs and notches. At the trailhead, concrete cells are charcoal kilns from the logging era. Some paths also follow roads and fairways from D. H. Day’s resort and golf-course plan; the club closed in 1942.