Pleasant Mountain sports a network of trails and some of the most exceptional views of surrounding mountains and lakes.
The top of Pleasant Mountain provides a glorious view of Mount Washington and White Mountains. Credit: Courtesy of Ron Chase

Pleasant Mountain is one of the most popular mountain hikes in Maine. The 2,006-foot peak is the tallest mountain in southern Maine and certainly one of the busiest in the area. A network of trails offers several hiking alternatives, most include exceptional views of surrounding lakes and distant mountains. 

Consisting of a 10-mile trail system managed by Loon Echo Land Trust, four trailheads ultimately lead to the highest summit, where there is a closed fire tower and truly phenomenal views from cliffs facing west toward the White Mountains in New Hampshire. The fine folks at Loon Echo do an outstanding job maintaining the trails, posting valuable signage and providing as much parking as possible at the trailheads.

I don’t recommend hiking alone in winter, but if you’re so inclined, Pleasant Mountain is a good choice. On a nice day, you’re almost guaranteed to meet a multitude of fellow mountain travelers. I’ve probably hiked Pleasant more than 100 times during the past 40 years. To the best of my recollection (which is suspect at my age), I’ve never been alone on Pleasant Mountain.

Hikers negotiate the Ledges Trail on Pleasant Mountain in Bridgton. Credit: Courtesy of Ron Chase

After a succession of early February bad weather days and a seemingly endless succession of old age medical appointments, I was in need of a mountain fix. An exceptional winter mountain forecast sealed the deal. My attempts to recruit friends or family proved unsuccessful. Unwilling to squander such a beautiful day, I settled on the obvious choice — Pleasant Mountain.

My preferred Pleasant Mountain trails are Ledges and Southwest Ridge. At a distance of 1.8 miles and ascending from the southeast, Ledges offers the shortest route to the summit while Southwest Ridge is the longest. Both are exceptionally scenic. According to my unofficial tally, Ledges receives the heaviest traffic, so that was my selection. My book, “Maine Al Fresco: The Fifty Finest Outdoor Adventures in Maine,” narrates an early winter traverse of Pleasant via Southwest Ridge and Ledges Trails.

Bluebird skies, seasonably warm temperatures, light winds and a nearly full parking lot greeted me when I arrived at the Ledges Trailhead. Fortunately, there were a couple of empty spaces in the Pleasant Mountain parking area. A quick inspection of the trail confirmed what I suspected: The surface was well-packed, so I would need microspikes. I wore spikes throughout the outing, encountering icy sections and a few exposed spots on the ledges. A large group was doing its best in bare boots and one family was equipped with snowshoes. Everyone else I met was wearing spikes.

After climbing icy stone steps and passing a kiosk, I experienced easy hiking on a gradual incline in a sparse hardwood forest. Winter trekking on a snow-packed trail is easily my favorite hiking surface. The additional cushion is gentler on my aging joints. Early on, I met a trail runner finishing his arduous workout. Once a rarity, trail runners have become more common in recent years.

Following two narrow stream crossings, I began ascending a series of switchbacks, where I met a couple who reported stunning conditions on the ledges and at the summit. Others echoed their observations as I continued my climb up Pleasant Mountain.

Moose Pond is seen from the Ledges Trail on Pleasant Mountain.
An overlook on the Ledges Trail provides a panoramic view of Moose Pond and the hills beyond from Pleasant Mountain in Bridgton. Credit: Courtesy of Ron Chase

The often crowded overlook at the lower end of the ledges was devoid of hikers. I stopped to embrace the panoramic view of Moose Pond and the hills beyond. For many years, there was a wooden cross at the overlook erected in memory of a woman who frequented Pleasant Mountain. It vanished a few years ago. I miss it.

I encountered more hikers as I progressed up the open ledges (for which the trail is named) offering bountiful views of the south summit. They were carefully negotiating icy sections. Several eagerly volunteered more glowing reports of light winds and marvelous vistas at the top of Pleasant Mountain.

Leaving the ledges behind, the trail rose steadily to a junction with Southwest Ridge Trail, which connected from the west. Just above, a steep icy section required careful maneuvering. The gradient diminished as I proceeded toward the top, where a trio of hikers cheerfully announced that I would have the summit of Pleasant Mountain to myself.

But not for long.

Two parties soon joined me to enjoy the wonderful views of Mount Washington and the White Mountains and soak up the sun in a wind-free environment. The verdict was unanimous: Ours was an extremely rare and truly glorious day on Pleasant Mountain.

A tower is seen atop Pleasant Mountain.
Clear skies welcome a hiker to the summit of Pleasant Mountain in Bridgton. Credit: Courtesy of Ron Chase
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Ron Chase, Outdoors Contributor

Ron Chase resides in Topsham. His latest book, “Maine Al Fresco: The Fifty Finest Outdoor Adventures in Maine” is now available at His previous books are...