Wednesday, September 23, 2026

Sheepfold to Brooks Road Area (Middlesex Fells Reservation)

Sheepfold to Brooks Road Area (Middlesex Fells Reservation)

Hike Type: Spaghetti Loop
Distance: 4.12 miles
Elevation: 269 feet
My Time: 1 hour, 21 minutes
Book Time: 2 hours, 11 minutes
Parking: Parking for many cars at main trailhead.
Hiking Challenges: Middlesex Fells Reservation


The Hike 
Time for the first hike of fall! It was a chilly 60 degrees out and just beautiful. This is my first time hiking in the Sheepfold area outside of the Skyline Loop, so I was interested to see what it held! This hike's primary objective was to kill time before Back to School Night tonight... ugh...

Right away there were dogs misbehaving in the parking lot (off-leash...), but I scooted around them and made my way to the Reservoir Trail - my main goal was to connect the dots between here and the trails I have already hiked south of here (roughly Brooks Road). I forgot my hiking shoes at home, so I hiked in my sneakers, which was mostly fine until I got onto the gravel Chandler Road, which simply felt unpleasant. 

Chandler Road continued straight as the footpath turned left (the straight part of the road went into the Winchester Water Supply land). After leaving the road, the Reservoir Trail started a joyful wiggle that I'm sure the mountain bikers love. There were some newer-looking multi-use trail signs that I hadn't seen before. The Reservoir proper was looking beautiful through the trees, and it was mighty tempting, but I minded my business and kept on moving.

I deviated from the Reservoir Trail at 4-1 to get a little spur and made my way to cross Brooks Road before making a sharp turn onto the Cross Fells Trail, which marked my southernmost point - time to fill in some gaps now! The Cross Fells Trail was ledgier with blue skies above - so pretty!

I enjoyed the paths around Gerry Hill and naturally the hike became louder as I got closer to I-93. I passed a bunch of porcelain berries (according to Seek) near the Fellsway, which were absolutely stunning in color and apparently super invasive. I turned left at Gate 27 and hiked on a path paralleling the Fellsway before disappearing back into the woods. 

The trail actually went over a bridge! I was thinking of saving the bridge for later as I connected the dots. The bridge went over the access driveway to the Sheepfold area. I made a sharp left here onto the green-blazed route. 4-3 to 3-3 was delightfully wide and soft, and I finally ran into my fisrt person outside of the parking lot as I approached the bridge for a second time (to finally cross it!).

The trail skirted a grassy area that led to Gate 25, and then I worked my way up and down the Soap Box track to catch the Reservoir Trail and make my final return. This whole area was super fascinating and overall quite nice to explore! Only bummer was that I noticed a little under-butt/hip pain after this one? I found it funny that I could beat the life out of myself on Carter Dome but two days later get a more lasting pain at the Fells? Silly!

Step-by-Step
- Park at main Sheepfold parking area.
- At kiosk, turn left towards Reservoir Trail.
- At terminus, turn left onto Reservoir Trail.
- At D3-8, turn right to follow Reservoir Trail and follow orange blazes.
- At C4-1, turn sharply left onto Gerry Hill Path.
- At C4-2, turn around.
- At C4-4, continue onto Reservoir Trail.
- At C4-8, turn left onto path.
- At C4-9, turn left onto Cross-Fells Trail.
- At C4-7, turn left onto Brooks Road.
- At C4-6, turn right onto path.
- At C4-4, turn left onto Reservoir Trail.
- At C4-5, turn left onto Brooks Road.
- At Gate 27, turn left.
- At jct., turn sharply left onto Mtn. Bike Loop.
- At D4-3, turn right onto Gerry Hill Path.
- At D4-2, turn right.
- At C4-3, turn left.
- At C3-3, turn around.
- At C4-3, stay left.
- At D4-1, turn left onto Mtn. Bike Loop.
- At jct., turn left.
- At Skyline/Reservoir jct., turn around.
- At jct., turn left onto Mtn. Bike Loop.
- At jct., hike spurs to parking lot and continue on Mtn. Bike Loop.
- At jct., hike spur on right to Gate 25, then continue on Mtn Bike Loop.
- At jct., turn left.
- At D3-6, hike to Soap Box Derby Track.
- At jct., turn left onto Reservoir Trail.
- At jct., turn left onto path to parking lot.

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