Skyline Trail Loop via Wright's Hill Trail (Middlesex Fells Reservation)

Skyline Trail Loop via Wright's Hill Trail (Middlesex Fells Reservation)

Hike Type: Lollipop Loop

Distance: 8.18 miles

Elevation: 1,089 feet

My Time: 2 hours, 48 minutes

Book Time: 4 hours, 38 minutes

Parking: Parking for ~15 cars at Bellevue Pond.
Hiking Challenges: 52 Hike Challenge 2026, Middlesex Fells Skyline Trail, Operation Alaska Benchmark Challenge

The Hike 

The end of the school year has been mentally beating the life out of me, so I decided it was time to physically beat myself up too and revist the Middlesex Fells Skyline Trail. I hiked the loop once before, but I did missed the final segment coming down from Wright's Tower, so I guess I had never officially hiked it all. Plus, I found a patch for it on Ebay! It seems to be an older Boy Scout patch, but it still counts! It was warm out in the low 80s.

Bellevue Pond had become mostly a grassy meadow now with just a very small pool of water in the back. I hiked in and decided to take the Wright's Tower Trail first to access the Skyline Trail for views and a little bonus elevation. This was also the pollen-iest day of the year - I was already coated in the yellow toxins. The sunny part of the trail was HOT. The shade was okay. I made my way up and ran into a bunch of teens, so I took my picture at the view and blasted off! I liked seeing the view of Boston in it's new green foliage.

Now officially on my loop, I admired how shaded the woods were. As I climbed up and over the first little knob after D6-2, I passed some baby blueberries. I had to really pay attention to blazes since there are so many criss-crossing paths in the Fells, many of which are not even on thge map. I passed a very stinky duo, which was crazy, because usually I'm the stinky one!

I worked my way up and over the Panther Caves and then passed a bone-dry swamp just after. I took a swig of my warm Nalgene and hit the junction with the Cross-Fells Trail right at the first mile marker. It was fun to hike in this area, it felt a bit like Memory Lane! There was a little swamp before C5-1 and the first of many confusing junctions - which is always my beef with the Middlesex Fells - blazing is either aggressively abundant or severely lacking, and there is simply no in-between.

The Skyline Trail paralleled the Mountain Bike Loop in a swampy area and then joined on a gravel path, then passing a concrete water tank(?) and a stone block in the ground that might mark the town line btween Winchester and Medford, even though it didn't exactly match the map. I descended to West Dam Road, which had a small wetland with a very shy turtle. There were a few annoying bugs buzzing about, but not enough to warrant bug spray.

The trifecta of the Skyline Trail, Reservoir Trail, and Mountain Bike Loop coincided and rose steadily on a gravel path after crossing West Dam Road, and later Skyline and Reservoir veered left away from a metal water tower, splitting from each other a minute or so later. I could feel the pollen granules in my eyes and a large amount of spider webs on my skin. 

I was enjoying this western portion of the loop becuase I had hiked most of it previously in winter, so I really wasn't recognizing most of it! I was also atonished how in the right lighting I could see how thick the pollen was in the air. I climbed up and down another knob to cross Molly Spring Road, and I could hear an owl when I was working my way up and over Nanepashimet Hill, which was SUPER sunny.

There was an old metal beam and rock harlqeuin flowers on the knob after B3-12, and then I had to maneuver a few blowdowns before B3-6. I passed a big cloud of what smelled to be the Devil's Lettuce, but the source was unknown. I could start to see the reservoir though the trees, which was exciting!

I've always been confused about the roads around the reservoir. It seems the roads circling the North Reservoir are open, and were signed as such, even though they're resitricted on the map. I crossed paths with a wild amount of shirtless trail runners in running vests in this stretch, which had really pretty flat pine-y woods.

As I hiked along Hillcrest Parkway, I admired some of the massive hydrangeas in peoples' yards. There is also a good amount of roadside parking here, which was good to know. I hiked past the North Reservoir's dam, which is closed to the public, and I eavesdropped on a duo's gossip session about a friend who inherited a bunch of money recently, it was a very fun 10 seconds!

The Skyline Trail goes back into the woods and zig-zags down to the reservoir's outflow stream, which was just a trickle. I crossed the creek on a NEMBA bridge, enjoyed a nice breeze, and began to make my way towards the Bear Hill Area, which was still pretty foreign to me. 

I almost got lost at C1-4 due to an unsigned and unblazed turn, but thankfully my brain thought "this feels wrong." The trail hit a low point just after with some rotting bog bridges just before rising to the Dike Road.

I climbed up the side of Bear Hill, passing an older hiker and his well-behaved and possibly overheating golden retriever and after the height-of-land, the trail became full of a wonderful, floral scent with no flowers to be seen!

As I approached the Sheepfold area, the Skyline Trail became more of an open trail, crossing knob after knob, many of which were open, and they were HOT. Winthrop Hill had a sunny bench overlooking some grasses at the top, and I almost got lost again at D3-1.

I maneuvered around an impressive blowdown just after C2-8 and then skimmed the outside perimeter of the Sheepfold area next to a swamp. There seemed to be a good amount of folks out at the main Sheepfold area, but the Skyline Trail was still full of spiderwebs! I was happy to be in the shade, though.

The Skyline Trail briefly followed a paved path as I-93 roared in the distance. The trail cut through a parking area, crossing a couple of paved single-land roads, and then turned left onto a nice boardwalk. I noticed a bit of a hot spot on both of my big toes and right heel, but naturally decided to avoid it. I felt myself finally starting to tire out around the six-mile park, but I kept on moving!

I joined the Cross-Fells Trail again and almost got lost... again soon after. The Cross-Fells left soon after joining and I officially finished all my water (only 1L, oops) on Silver Mine Hill. It was hotter than I was ready for! I joined the Cross-Fells yet again at C5-18 and crossed paths with a trail running trio I saw over by the North Reservoir - only this time they were power hiking. The two guys were leading and the woman was suffering behind, I felt kind of bad for her.

I finally made it to my final push up to Pine Hill and I was tired! Eight miles after school in the heat took more out of me than I was ready for! I decided to look for all three discs again: I found the northernmost one, an arrow, and it was pointing to a summit disc. But... I don't think I'd seen this one before? On a higher rock to the east was another arrow, which I think I had seen before. Wait this is three? I already knew about the magnetic station, so there's four up here? I worked my way over, and found ANOTHER arrow?! Five discs?! This was beyond exhillerating to me and fully brought me back to life. 

Riding the high of discovery, I continued onto the tower and was SHOCKED to see how insane the pollen haze had become - it was so thick I couldn't even see the Blue Hills! 

From here, I descended back along the yellow trail and made it back to the car, dusting myself off before driving back home. Another patch "earned"!

Step-by-Step

- Start hike on Quarry Road.

- At jct., turn right onto Wright's Tower Trail (yellow).

- At tower, turn left onto Skyline Trail (white).

- Follow Skyline Trail clockwise around, back to tower.

- At tower, descent via Wright's Tower Trail (yellow).

- At terminus, turn left onto Quarry Road and return to car.

Middlesex Fells Reservation Map

Photo Album