Hancock & Hemenway Hills (Blue Hills Reservation)

Hancock & Hemenway Hills (Blue Hills Reservation)

Hike Type: Spaghetti Loop

Distance: 4.18  miles

Elevation: 761 feet
Time: 1 hour, 50 minutes

Hiking Challenges: Blue Hills Winter Trace, Blue Hill Grid

The Hike

This hike is brought to you by some vague exploring. The plan was to tackle some of the trails around Hancock & Hemenway Hills - I parked at my favorite parking spot at Park HQ across from the state police barracks, and started my climb up the Skyline Trail to Hancock Hill. Instead of climbing all the way to the top, I turned left at 1172 onto the Hancock Hill Path, which is a bit of a vague intersection, but once you see it it makes sense. The Hancock Hill Path starts off pretty steep but quickly mellows out, and just as my heart rate was going down a red squirrel (my arch nemesis) darted across the trail, scaring the life out of me! I made a sharp right at 1160 onto the Breakneck Ledge Path which posed the question - what exactly is Breakneck Ledge? The trail follows the floor of a long ridge, maybe that’s it? Not sure! It’s a beautiful trail, nonetheless.

At 1178 I turned left onto the Hemenway Hill Path, which felt like road less traveled for sure. Near the top, there was an unmarked spur that led to a ledge with no views. Maybe there were some decades ago? I followed to 1154, then turned left onto Jeffries Trail, which was covered in soft pine needles, and then to Skyline so I can get to the summit of Hemenway Hill and to see the view toward Big Blue. I retraced my steps back to 1154, and then continued hiking the Jeffries Trail, which was very quiet and made me feel very peaceful. There were a couple spurs to either an old trail or an old view maybe? They seemed to lead nowhere. Toward the end of the Jeffires Trail the forest is very young with very obstructed views of Boston, and the trail eventually ends with a caged stream and well? Very curious on the history and purpose of this. 

Next I hiked the Base Path, which was relatively uneventful, and then the Circle Path, which followed a col between what might be Hancock Hill and Breakneck Ridge? There was a mysterious blue beach chair perched along the trail, and across from the chair was a footbed to what might possibly be breakneck ledge - I followed it and found a few nice views, but nothing spectacular. It was for sure strange to see the chair!

I meandered my way to the circle part of the circle path, and then hiked on Skyline to the summit of Hancock Hill - this is such a beautiful area with wayyyy too many unmarked trails. I found what I believe to be the high point, and then did my best to follow the Hancock Trail to my favorite view in the reservation. There were a few yellow blazes splattered about which helped me down the steep section just before 1201. I noticed how orange the scenery was getting, so I had another round of power hiking to maybe catch a sunset - oh boy!

I made it back to the Skyline Trail and quickly hiked back up Hancock, but the sun was behind some clouds and dipping behind Great Blue Hill - it was beautiful! But according to my rules, did not count toward the Sunset 6 challenge. Lots of airplanes were flying by as I worked my way down the Skyline Trail back to my car, overjoyed with how nice the day turned out to be. 

Step-By-Step

• Park across from State Police Barracks on Hillside St.

• Start hike by crossing Hillside St. and climbing halfway up Hancock Hill via Skyline Trail.

• At 1172 (hard to see), turn left onto Hancock Hill Path.

• At 1160, turn right onto Breakneck Ledge Path.

• At 1178, hike to 1180 and retrace steps to Hemenway Hill Path.

• At 1154, turn right onto JeffriesTrail.

• At 1150, turn left onto Skyline Trail to Hemenway Hill Summit.

• Retrace steps to 1154, continue down hill on Jeffries Trail.

• At 1182, turn left to hike Base Path to 1183, retrace steps, and continue on.

• At 1185, continue straight onto Circle Path.

• Hike Circle Path all the way to its circle, then follow Skyline Trail to summit of Hancock Hill.

• Follow Hancock Trail to 1201.

• At 1201, turn right onto Hancock Hill Path.

• At 1172, try desperately to see the sun set through the clouds behind Big Blue, accept defeat, and retrace steps back to car down the Skyline Trail.

Map of Blue Hills Reservation

Photo Album