“A” Trail, “B” Trail, Homestead Trail, Long Pond Trail

A Trail in orange; Round Top Mountain in blue; B Trail and Long Pond Trail in pink, accessible Homestead Trail in lavender.

The A Trail, which shares a parking lot with Round Top Mountain and is one of several hikes in the 6,800-acre Kennebec Highlands, has been created for both mountain bikers and hikers. But I think it’s probably more popular with bikers. That being said, it’s not bad for people on foot. After about 3.3 miles of gradual, easy uphill through dappled forest, you get to a lovely lookout. If you want to summit McGaffey Mountain, you’ll walk another 1.2 miles along a ledgy ridge to the viewless mountaintop. There are rocky outcrops here that make for a good resting spot, though.

There are lots of additional bike trails not included on the official map. The one I followed connected to the system of woods roads that crisscross the highlands and are better for biking and skiing than walking.

Additionally, if you cross Watson Pond Road, you’ll find the B Trail system, which includes a ~1-mile path down the hill to access Long Pond (and a good spot for swimming), as well as the 0.3-mile accessible Homestead Trail.

And while Long Pond Trail is made with switchbacks, it has a notable descent! Be prepared to get a bit winded. You can also explore the flatter ~1.7-mile B Trail loop, which makes a big loop around the old homestead site, now a gathering site for gatherings and programs. We found the B trail, which was not blazed, to be hard to follow at times. Again, this system, with the exception of the Homestead Trail, was made with bicyclists in mind.

Directions: A large parking lot is located at the corner of Watson Pond Road and Wildflower Estates, 4 miles south of Route 27.