Hiking around the island
Although Monhegan is barely a square mile in area, it has numerous hiking trails for those seeking an adventure along the highest cliffs off the coast of Maine or for those who want a easy stroll near the ocean. There are 18 trails that cover roughly 17 miles of terrain.
Trail 1: Cliff The trail around the island: spectacular views. You may need several hours to complete this trail, parts of which are exposed and strenuous.
Trail 3: Underhill Fairly level trail through woods, gentle incline to Burnthead. Take Lobster Cove Road beyond the Trailing Yew and turn left into woods just beyond red house with picket fence.
Trail 4: Burnthead Next to Monhegan House, ascend steep Horn Hill. At top, follow signs to right. Level trail, mostly in meadows, to panoramic views of 140-foot headland.
Trail 5: Gull Cove Next to Monhegan House, ascend steep Horn Hill. At top, turn left toward Hitchcock House and look for trail marker #5 on right. Fairly easy trail to Gull Cove.
Trail 6: Alder Narrow but level trail. Take Main Road north to the library and follow branch to right (Tribler Road) along meadow. Just before the end, veer left at the #6 sign. Trail runs through woods. At junction with #5, go left to join the Whitehead trial #7 or right, onto #5 for a level trail to Gull Cove.
Trail 7: Whitehead Moderate trail with some climbing, rewarded by extensive panorama of the headlands. Take Main Road past the library and to the right up the steep Lighthouse Hill Road (watch for driftwood sign). Continue on road past the lighthouse and museum buildings and across the ball field behind them, into the woods. Continue downhill and on the right is the entrance to #6 (above); on the left is #9 (below). Next you will encounter #1a on left and right; these take you to the coast but miss the views from Whitehead. Continue up one final hill to the headland. To return to another path, retrace steps to #1a; #1 is steep in both directions.
Trail 9: Red Ribbon Pretty woodland trail leading to Whitehead trail. Follow Main Road as for #7 and turn right at red ribbon tied on tree.
Trail 10: Blackhead Main trail head for several other trails. Wide path through woods and marshy spots almost to the end, but the traverse to the headland itself is difficult, though views are rewarding. Follow Main Road from Village past library; bear left at fork just beyond Schoolhouse onto Cathedral Woods Road, following driftwood sign. Trail #10 begins where road ends.
Trail 11: Cathedral Woods A favorite woodland trail for all ages. Follow Main Road for #10 as above; take the second trail to the right. Some distance into the woods there is a fork at a big rock. The right fork (Trail 12, Long Swamp leads to Little Whitehead. The left fork continues #11 to Trail #1 at Squeaker Cover, a beautiful place to cautious surf watching. Turning left off this fork before reaching #1 is #16, a connector to #10.
Trail 14: Pebble Beach Pretty woodland trail over rock outcroppings and down a steep hill to Seal Ledge area. Follow directions to #10 as above, then turn left beyond the end of the road. Follow signs to #14.
Trail 15: Evergreen Moderate route to Seal Ledges and Pebble Beach. Pleasant woodland trail forking left off Blackhead trail (#10) beyond the entrance to trails #1 and #14.
Trail 16: Maple Meandering trail between Blackhead trail and Cathedral Woods. Trail is not difficult but deer trails may prove confusing.
Trail 17: Fern Glen Woodland trail to Pulpit Rock area. Follow #10 (above) to trail head on left beyond #15. At junction take left path. Trail to #1 is moderate but between #1 and the headland at Pulpit Rock are some difficult areas.
Trail 18: Station Hill Easier route to Pulpit Rock than #17. As above, follow #10 to trail head on left beyond #15. At fork take right path.