Middlesex Fells

As autumn came to New England, I went searching for good fall hikes in the area and the Middlesex Fells came up as an option, specifically the Skyline Trail with views of Boston from Wright’s Tower. The Fells are managed by the Massachusetts Department of Conservation & Recreation, who also oversee the state parks. At over 2,500 acres, the Fells have more than 100 miles of trails as well as mountain biking, boat rentals, and an off-leash dog field. The reservation is split in two by route 93; on this visit we hiked on the western side, which is also the mountain biking side. The Skyline Trail loops around the three reservoirs (North, Middle, and South) in the western Fells, sometimes coinciding with the Reservoir Trail and Mountain Bike Loop, and passes by Wright’s Tower at the trail’s southernmost point. According to the DCR website, the Skyline Trail is 6.9 miles, but people on AllTrails and other sites said it was longer, with distances ranging up to 8.5 miles. AllTrails also had multiple people comment that the trail was not well marked in places and could be confusing where it intersected/merged with/separated from other trails.

We began at the Sheepfold parking lot, which serves as a main access point for a lot of the western trails. It then took us over fifteen minutes to find the Skyline Trail, so yes, I would agree with the people who said that the trail markings need some work. Within another 30-45 minutes, we lost the trail again, and it wasn’t just us, because in less than 5 minutes we met two other groups with the same problem. We ended up backtracking until we found the turnoff down a pile of rocks that was apparently the trail, marked with an inconspicuous blaze on an out of the way tree. Fortunately, from there the trail was marked better, at least well enough that we didn’t lose it again.

Thanks to our wayfinding delays, we only made it a mile or two on the trail before we stopped for lunch by the North Reservoir (surprise, it was peanut butter and jam sandwiches and bananas). From there, we rounded the top of the reservoir and started heading south along the west side of the reservoirs. This part of the trail tended to be smoother and flatter, especially any parts that were shared with the mountain biking trails, so we made better time until we got to the bottom of the South Reservoir. There, the trail split off into a network of rocky ups and downs that eventually meandered its way to Wright’s Tower. The view here was nice, though we were hoping for more fall colors. The final couple of miles remained quite rugged, and I ended up cutting off the last bit by crossing over to what Google maps¹ had labeled as the Railway Trail that was much flatter.

Rocky, hilly, root-y trail

¹Google maps was somewhere between mostly useless and not greatly helpful in navigation because of the very large number of side trails that it didn’t have properly mapped. Even the main trails weren’t labeled correctly, if they were labeled at all, so I wouldn’t rely on Google to get you to a particular trail, though it’s okay for tracking your general progress.

In the end, it took us 5.5 hours to complete the loop, which included losing our way multiple times, lunch, and some time at Wright’s Tower (I'd estimate closer to 4 hours of actual hiking). The entire trail is unpaved, either dirt or rock, though the west side of the loop has some areas that are flatter and smoother while the rest (north, south, east) is very rocky and hilly. As discussed above, the trail markings are particularly poor in the northeast quadrant of the trail. Other than Wright’s Tower, there aren’t any great vistas, and we barely even got to see much of the reservoirs. I would hike the trail again, but without the expectation of seeing many skyline views and as more of a woods trail, not a scenic one.

View of Route 93/Boston from Wright's Tower

Parking was free at the Sheepfold and at a number of the other parking lots around the Fells, though not all the lots are free. It was pretty busy on a fall Saturday with lovely weather, but not crowded. Sharing the trails with mountain bikers at times wasn’t bad; the sections weren’t too long and nobody was riding too recklessly. Final verdict: The Skyline Trail wasn’t bad, and I’d hike it again, but I wouldn’t necessarily put it on a list of amazing fall hikes. There are also a number of other trails at the Middlesex Fells that are possibilities for future adventures.