Hiking Pleasant Mountain, Maine: Southern Maine’s Highest Peak

Rising 2,006 feet above the lakes and forests of western Maine, Pleasant Mountain is the highest peak in the southern part of the state and one of the great landmarks of the Sebago Lake region. With a well-loved network of trails, a historic fire tower on its summit, sweeping views of the White Mountains, and Maine’s oldest ski area on its slopes, it is a favorite of hikers in every season. Here is a guide to hiking Pleasant Mountain, Maine.

About Pleasant Mountain

Standing 2,006 feet tall, Pleasant Mountain is the highest mountain in southern Maine. Its long ridge stretches between the towns of Bridgton (in Cumberland County) and Denmark (in Oxford County), about an hour’s drive northwest of Portland. Much of the mountain is conserved: the Loon Echo Land Trust owns more than 2,000 acres here and maintains the roughly 10-mile network of hiking trails, keeping this beloved peak open to the public and protected for the future.

Choosing Your Trail

There are several trailheads on the mountain, each with its own character:

• Ledges Trail: the most popular and most direct route to the summit, rewarding hikers with wide-open views from the exposed ledges just below the top.
• Bald Peak Trail: a blue-blazed climb on the west side that leads up over Big Bald Peak before joining the main summit ridge.
• Fire Warden’s Trail: the longest route to the summit, passing the site of the old fire warden’s station on its way to the top.
• Sue’s Way: an orange-blazed connector from the Bald Peak Trail up to the top of the ski area, with fine views over Moose Pond.
• Southwest Ridge Trail: a longer, scenic ridge walk for those wanting more time on the mountain.

The trails are generally rocky and can be steep, so sturdy footwear is a must, but they are well marked and maintained by the land trust.

The Summit, the Fire Tower, and the Views

The summit is crowned by an old fire tower, built around 1920 and one of roughly 70 such towers that still stand on Maine’s mountaintops — a reminder of the days when watchmen scanned the forests for smoke. The reward for the climb is the view: to the west rise the White Mountains, with Mount Washington visible on a clear day, while to the east and south spread Moose Pond and the shining lakes and countryside of the Sebago region. In autumn the surrounding hills blaze with red, orange, and gold, making Pleasant Mountain one of the finest foliage hikes in the state.

Maine’s Oldest Ski Area

Pleasant Mountain is also a piece of Maine skiing history. The ski area on its slopes opened in 1938 as Pleasant Mountain — the oldest major ski area in Maine, home to the state’s first ski patrol and, in 1954, its first chairlift. From 1988 to 2022 it was known as Shawnee Peak, but after new owners took over, the historic Pleasant Mountain name was restored in 2022. In winter its lift-served trails and night skiing draw crowds overlooking Moose Pond, making the mountain a true four-season destination.

Know Before You Go

• Wear good footwear. The trails are rocky and steep in places, with open ledges near the top.
• Bring water and snacks. There are no facilities on the hiking trails, so come prepared.
• Check the weather. Conditions change fast on the exposed summit; skip the ledges in storms and dress in layers.
• Tread lightly. Follow Leave No Trace, stay on the marked trails, and respect the Loon Echo Land Trust land that keeps this mountain open to all.

More Western Maine Adventures

Pleasant Mountain pairs well with the other hikes of western Maine’s Lakes Region and mountains. A short drive away, the easy climb up Hawk Mountain in Waterford offers big views for little effort, while the Fryeburg area has another fine short summit in Mount Tom. Travelers heading west from central Maine often pass through the Kennebec Valley; our own town of Winslow, with its colonial-era Fort Halifax, makes a fitting stop on the way into the hills.

Frequently Asked Questions