Since the autumn days spent at the Fryeburg Fair as a kid, I’ve enjoyed visiting the Oxford County town. But when I think of hiking, Fryeburg is a blip on my GPS as I continue to the White Mountains. With the Kancamangus Pass and Crawford Notch just miles away, some of the most beautiful hiking in New England sits across the state line.

However, this spring I’ve taken the time to explore the hiking options in the Fryeburg area and came away pleasantly surprised. While there aren’t any hikes with the scale and grandeur of those in the nearby Presidential Range, there are more than enough to keep any day hiker busy and happy. The shorter, easier trails are also a boon to families looking to get young kids out and exploring.

Here’s a short list of Fryeburg-area recommendations.

The best-known hike in Fryeburg is Jockey Cap, a 200-foot peak just off Route 302. In the 1930s the hill was briefly a ski area – and home to Maine’s first rope tow – but has since found a second life as a family hiking destination. The quarter-mile climb from the parking lot to the peak is steep but quick, making a round trip of less than half an hour likely. But it’s worth lingering at the top for the panoramic view, from nearby Sebago Lake to farther Grafton Notch and Mount Washington. Probably the neatest part of Jockey Cap is the unique bronze and stone sculpture that sits on its peak. The piece, dedicated to Arctic explorer Robert E. Peary, details all the surrounding landmarks in brilliant profile.

Just a few miles down Route 302 from Jockey Cap, the Mountain Division Trail offers a few miles of pleasant, easy hiking. The paved trail, which follows the old Mountain Division railway line, covers four miles between the Maine visitor center and Portland Street. The trail provides scenic views of the surrounding mountains, as well as amenities like trailside benches and restrooms at the visitor center. Since the trail is paved, it’s a welcome destination for both cyclists and hikers. The Fryeburg trail is a small part of a long-planned project to create a hiking trail that runs the length of the old railbed, from Fryeburg to Portland.

Five miles south of Fryeburg, Brownfield’s Peary Mountain is a 2.4-mile out-and-back hike that covers two peaks in its short distance. Starting from Farnsworth Road, the trail climbs steadily along ledges and ridges looking over Lovewell and Pleasant ponds, with Mount Tom and Pleasant Mountain looming in the distance. The trail climbs first to the true peak of Peary, and then to a slightly lower one to the southeast before doubling back.

A few miles east of Fryeburg, a trailhead on Menotomy Road at Inglenook Farm offers another short hike in Mt. Tom. The 1.2-mile path climbs the gentle northern slope of the 1,000-foot peak, ending at a knoll on the summit. The southern exposure of the peak is a relatively sheer cliff, rewarding hikers with a view of the Saco River and Pleasant Pond. Trails climb both the northern and western sides of the mountain, and the hike can easily be turned into a four-mile loop by backtracking on the Menotomy Road.

While they’re not in Fryeburg, it’s difficult to talk about hikes in the region without mentioning those on Pleasant Mountain. A 10-mile trail network, managed by the Loon Echo Land Trust, spans 1,500 acres on and around the Bridgton Mountain. From trailheads on Denmark and Mountain roads, hikers can reach four distinct peaks – the 2,006-foot summit, the shorter southwest summit (1,900 feet), Big Bald Peak (1,932) and the top of the Shawnee Peak ski area. The well-designed network makes it possible to hit these peaks individually, or string all four together into one long hike. From the towers near the summit, a clear day allows for views of both the Presidential Range and the Maine coast.

South of Fryeburg and Bridgton, Burnt Meadow Mountain is a final favorite in the region. A parking lot on Route 160 provides access to the 3.6-mile loop trail, which climbs to an open, rocky summit. The trail splits a few hundred yards after the start. Blue blazes mark the North Peak Trail, which climbs steeply over some rock scrambles and ledges to cut directly to the summit. Yellow blazes mark the Twin Brook trail, a longer route that follows a running stream and gradually climbs to the summit. Unless you’ve got a real need to stick to the more gradual slopes, the best way to tackle Burnt Meadow Mountain is by climbing up the North Peak Trail and descending via the Twin Brook Trail. A spur trail lets hikers bag another summit by climbing three-quarters of a mile to Stone Mountain.

Josh Christie is a freelance writer living in Portland. Along with his brother, Jake, and father, John, he writes about great Maine destinations for outdoors enthusiasts. Jake can be reached at

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