At 2,006 feet, Pleasant Mountain is southern Maine’s tallest mountain, home to Shawnee Peak Ski Area and a 10-mile trail network offering an array of terrain. This route on Southwest Ridge Trail is a moderately strenuous, familyfriendly hike that will leave everyone with a great sense of accomplishment.

From the well-marked trailhead, the wide, compacted dirt path ascends gradually at first through mixed forest for 0.6 mile, where it gains the ridge. From here, the trail weaves its way upward, alternating between slab granite and compact dirt. The views to the southeast get more and more stunning with each step. Moose Pond, the largest nearby body of water, glistens below (see Plan B).

The trail rises moderately along the exposed ridge, marked along the way with yellow blazes and rock cairns. Make sure your family is well prepared for the elements, whether it’s a warm, sunny day or a cool, wet one. Plentiful fields of wild blueberries thrive in this open habitat and (in season) provide the perfect sweet snack to fuel your climb.

After hiking 1.7 miles and gaining 1,546 feet in elevation, reach the Southwest Summit and take in the sweeping views of the southern Lakes Region. Most families will want to turn around here and retrace their steps back to the trailhead; however, if you have the energy and desire to push onward, consider hiking another 1.2 miles to the main summit. This additional route passes a small fire tower and a wide-open rocky field with superb views of western Maine and the White Mountains of New Hampshire.

Moose Pond’s calm waters, stunning scenery, abundant wildlife, and coves ripe for exploration make it an ideal body of water for family canoe trips. The 11-mile-long pond is divided into three distinct basins—the southernmost one being the most protected. From US 302 and Wilton Warren Road, take US 302 east for 2.8 miles to the causeway/bridge that separates the two largest basins of Moose Pond. The public boat launch is on the left.

Bridgton offers shopping, restaurants, an arts community, and a movie theater. North Conway, New Hampshire, is 15 miles away.