Railroad Trestle to Bear Hill (Middlesex Fells Reservation)

Railroad Trestle to Bear Hill (Middlesex Fells Reservation)

Distance: 2.28 miles
Elevation: 243 feet

Time: 48 minutes
Hike Type: Loop
Hiking Challenges: 52 Hike Challenge

The Hike

Back to the Fells! I had to drop off the four tubas that I stole/borrowed for TubaChristmas, but had an hour to kill. With the limited sunlight this time of year, the Fells made the most sense! I drove over to a corner I had not been to before, near Bear Hill. The parking was right off the highway and felt very... wrong, but it was marked on the map and allowed during daylight hours!

I started my hike on Dike Road and then veering left toward the highway onto an unblazed path that is on the map. The trail was nice, even though it paralleled I-93. There was plenty of needle ice in the shady areas, which was fun! There were occasional unmapped criss-crossing paths, but I stuck to paralleling the highway to moderate success.

The trail passed below a large concrete cylinder on to of Bear Hill - I would investigate that later. Eventually, some older yellow blazes began to appear on top of even older blue ones. I continued along, immersed in the sounds of nature, which in this case were cars, police sirens, and helicopters. Eventually, the path steeply descended to a gravel road at D2-7.

This started a lovely, flat stretch that I believe was an old railway (based on being named "Railraod Trestle" on the map). It first traveled between two high rock walls, and then over a fenced-in trestle, which was very fun and unique. 

I turned off of the Railroad Trestle trail at a second, smaller bridge, and wiggled my way to the more rugged Skyline Trail. I enjoyed the variety of terrain on this small hike. There was a lot of needle ice going up Winthrop Hill, which had a newer bench at the top. Just after there was a nice view into the interior of the Fells. I descended the hill and zig-zagged over to Bear Hill Road, which climbed gently up to Bear Hill.

Bear Hill had a massive concrete water tower (the cylinder mentioned before) with a really unique open-faced observation tower that seems to be in early-stage decay. The water tower was heavily fenced-in, and the observation tower was surrounded by a fence with multiple human-sized holes. I may or may not have scoped the area for a possible USGS disc, but did NOT tempt fate by climbing up the tower, but it was clear that many have/do, as evidenced by the massive amounts of graffiti. It was a super interesting area, for sure!

After descending Bear Hill on Bear Hill Trail, I then joined the Reservoir Trail, where I passed my first human of the day, and meandered back to Dike Road, which had a large amount of locked up manhole covers. I finished my hike soon after, and I made a note that I need to remmeber that 45 minutes in the woods is significantly better than nothing. I'm setting a soft goal of getting into the fells once a week until the 5pm sunsets come back and I can get back to the Blue Hills after school.

Step-By-Step

- Park at Gate 20 off of Fallon Road.

- Start hike on Dike Road.

- At jct., veer left onto footpath paralleling I-93.

- At D2-4, continue on footpath paralleling I-93.

- At D2-7, turn right onto Railroad Trestle.

- At D3-2, turn right toward Skyline Trail.

- At D3-1, turn right onto Skyline Trail.

- At C2-6, turn right onto trail.

- At D2-5, turn left onto Bear Hill Road.

- Summit Bear Hill, turn around.

- At C2-4, turn right onto Bear Hill Trail.

- At C2-3, turn right onto Reservoir Trail.

- At C1-6, turn right onto Dike Road.

- Return to car.

Middlesex Fells Reservation Map

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