Middlesex Fells is as close to wilderness as it can get for a reservation less than 30 minutes away from one of the country’s largest cities. Touring the Fells on the Skyline Trail, you may sometimes believe you are deep in the woods of New Hampshire. Indeed, do not mistake the Skyline Trail for a quick afternoon walk. At about 7 miles in length, it is a real hike that can take most of a day if you like to stop frequently. In addition to being long, it is also a difficult hike, with several ascents and descents likely to wear you out if you are not in shape.

From the parking lot, take the main trail, leaving Bellevue Pond on your left. Watch for white blazes a few yards after the pond on your right. They will lead you to Pine Hill, where an observation tower offers spectacular views to Boston in the background and the Reservation at your feet. The ascent to Pine Hill is a nice way to select the candidates to the Skyline Trail. If you are already sweating at this point, it may be better to settle down for a shorter or flatter hike (see Walking around the South Reservoir at Middlesex Fells and Walking in the South End of Middlesex Fells Reservation).

From the tower, you can then head north, following the blazes on the rocks to complete the hike. The Metropolitan District Commission and its partners have done an excellent job of blazing the trails across the Reservation, and you are unlikely to get lost if you proceed from one blaze to the next with attention, even without a map. Before leaving, however, take time to look at the map placed on the information board near the parking lot. Get a feel for the overall shape of the reservation and where the trail, identified with white blazes, will take you.

Some sections of the Skyline Trail are shared with other trails, and identified with other blaze colors (in particular, blue and orange) together with white marks. If you get lost but have a compass, remember than your parking lot is at the southern tip of the reservation, and that you are not supposed to cross a road on this trail. If you encounter one while heading south, it may be South Border Road; follow it south-southeast to get back to your car.