The Island is about .7 of a mile wide and 1.7 miles long. Monhegan is hilly: time required to walk a trail is greater than that needed on level ground.
From the wharf: Up the hill to the north-south Main Street. Turn right (south) to reach the center of the Village, restaurants and public toilets, Burnthead Trail, and Lobster Cove. Turn left (north) to reach the Library, the Schoolhouse, the Lighthouse Museum, Whitehead Trail (#7), etc.
All directions below are from the Village
The 2016 Trail map
Good for Day-Trippers
Whitehead (Trail 7): Moderate trail with some climbing, rewarded by panorama of headlands. Take Main Road past the Library and the school, bear right at fork up steep Lighthouse Hill road. Continue past Lighthouse and Museum buildings (see left), across the ball field, into the woods. (about 30 min. steady walking from Wharf.)
Burnthead (Trail 4): Easy trail but difficult climb to get to it. The closest headland to reach from the Village. Ascend steep Horn Hill next to Monhegan House. At top, follow signs on fork to right. Level trail, mostly in meadows, to panoramic views from 140 foot headland. (about 45 min. steady walking from Wharf.)
Lobster Cove: Follow Main Road south to narrow trail which leads to rocky coast and the wreck of the D.T. Sheridan, an old tugboat. Beautiful views, picnic on rocks, but stay well back from surf. (about 30 min. steady walking from Wharf.)
If you have a bit more time…
Trail 1: Cliff. Many parts are exposed, strenuous, and very difficult (see map). Spectacular views, but several hours are required to complete this trail.
#1a bypasses some difficult spots.
Trail 3: Underhill. Fairly level trail through woods, gentle incline to Burnthead. Take Lobster Cove road beyond Trailing Yew and turn left into woods just beyond red house with picket fence. Wet areas likely.
Trail 4: See above.
Trail 5: Gull Cove. Moderate. Next to Monhegan House, ascend steep Horn Hill. At the top, turn left toward Hitchcock House and look for Trail #5 on right. Fairly easy trail to Gull Cove, where you can view the headlands from sea level.
Trail 6: Alder. Narrow but level trail. Take Main Street north to the Library and follow branch to right (Tribler Road) along meadow. Look for Trail #6 sign on the left. Trail runs through woods. Look for a #6 where the trail branches. Follow the left branch to trail #7. The right branch connects with Trail #5 to Gull Cove.
Trail 7: See above.
Trail 9: Red Ribbon. Moderate. Woodland trail leading to Whitehead trail. Follow Main Street from Village past Library bear left at fork just beyond Schoolhouse onto Cathedral Woods Road. Turn right at red ribbon tied on tree.
Trail 10: Blackhead. Moderate but end difficult (see map). Main trail head for several other trails. Wide path through woods and marshy spots almost to the end. Traverse to the headland itself is difficult and trails difficult to follow. Follow Main Street as for #9. Trail #10 begins where road ends.
Trail 11: Cathedral Woods. Moderate. Follow Main Street for #10 as above; take second trail to the right. Some distance into the woods there is a fork at a big rock. The right fork (#12) leads to Little Whitehead. The left fork continues as Cathedral Woods #11. Soon you will see Maple Trail #16 on the left. Past Maple Trail, #11 leads to Trail #1 at Squeaker Cove, a place for cautious surf watching.
Trail 14: Pebble Beach. Difficult. Rough woodland trail over rock outcroppings and down a very steep hill to northern ledges. Follow directions to #10 as above, then turn left beyond the end of the road. Follow markers to #14.
Trail 15: Evergreen. Moderate to difficult. Another route to northern ledges. Woodland trail forking left off #10 beyond the entrance to trails #1 and #14.
Trail 16: Maple. Moderate. Meandering trail between Blackhead trail and Cathedral Woods (see #11).
Trail 17: Fern Glen. Moderate. Woodland trail to Pulpit Rock area. Follow #10(left) 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. Moderate. Another route to Pulpit Rock area. Follow #10(see left) and turn left onto #17. At fork bear right at #18 marker.