Hancock, Wolcott, & Hemenway Hills (Blue Hills Reservation)

Hancock, Wolcott, & Hemenway Hills (Blue Hills Reservation)

Distance: 3.47 miles
Elevation: 594 feet

Time: 1 hour, 51 minutes (1 hour, 18 minutes moving)
Hike Type: Lollipop Loop w/ Spur
Hiking Challenges: 52 Hike Challenge 2024; Sunrise Six

The Hike

Time for my first sunrise hike in a long time! Thankfully this time of year the sun doesn't rise until after 7:00am, so I actually got to sleep in! It was 22 degrees at the Hancock Trail trialhead with no wind and a dusting of snow. I put my headlamp on and got right to work.

I climbed the steep trail up the north side of the trailhead and then jumped onto Breakneck Ledge Path and then Circle Trail, both of which had a mixture of light snow, ice, and running water. I was thankfully much warmer than anticipated and was able to shed a couple layers down to my base layer. I turned onto the Skyline Trail and then the Hancock Trail until I made it to the stunning overlook of Boston, the Blue Hills, and the ocean.

I took out my Yeti filled with hot chocolate only to find out that my Yeti works a little too well - it was WAY too hot! I wish I had brought my camp cup - next time. I ended up pouring small bits of hot coco into the lid and sipping out of that, which worked! Hot chocolate on a cold hike is truly the best thing there is. It was so peaceful sitting up here without another soul around..... until I noticed some smoke coming from the Milton side of the park, followed by darker smoke, followed by fire! Apparently there was a pretty intense house fire just before sunrise (LINK TO ARTICLE).

I was starting to feel a little chilly around 7:00pm, and then I got to admire the sun rising above the clouds at 7:11pm. It was fun watching the surroundings light up, but the sun stayed behind the clouds for a while - the house fire was much more insteresting to watch - multiple firetrucks were there and a helicopter. 

After the sun was up the temperature was down to 21 degrees with a light wind, that would put the windchill into the teens. Once the sun was firmly up and behind a cloud I continued my journey. I wasn't really sure where I wanted to hike or how much I wanted to hike, but I was very grateful that I'm so familiar with the trails here that I don't really need a plan!

I ended up backtracking to the Skyline Trail and then the Hancock Hill Path (very flooded) to the Wolcott Path, where the sun began to shine over the clouds and on to the treetops - a truly beautiful golden light. I decided I'd make my way to Hemenway Hill to catch the view of Great Blue Hill in golden hour.... until I realized I accidentally skipped it and was suddenly on top of Wolcott Hill! I pivoted the plan again, and wiggled my way into Wildcat Notch and then over to the Hemenway Hill Path, and the extra climb was definitely worth it!

After Hemenway Hill I began to make my way back via the Breakneck Ledge Path, all while admiring the endless needle ice on the ground. My tummy began to act up at the end, which was the perfect timing, and I realized this may have been the first time I've hiked in the Blue Hills and never passed another human - what a great morning!

Step-By-Step

- Park at Hancock Trail parking.

- Start hike on trail to 1203.

- At 1203, continue onto Breakneck Ledge Path.

- At 1180, turn left onto Circle Trail.

- At 1170, turn left onto Skyline Trail.

- At top of the climb, turn left onto Hancock Trail.

- Stop and enjoy sunrise at view.

- Turn around.

- Turn left to continue on Skyline Trail.

- At 1172, turn right onto Hancock Hill Path.

- At 1160, turn right onto Wolcott Path.

- At 1141, turn left onto Skyline Trail.

- At 1117, turn right onto Dalton Path.

- At terminus, turn right onto Wildcat Notch Path.

- At 1115, turn right onto Wolcott Path.

- At 1122, turn left onto Rotch Path.

- At 1121, turn right onto Hemenway Hill Path.

- At 1154, turn right toward 1150.

- At 1150, turn left onto Skyline Trail.

- At 1162, turn left onto Breakneck Ledge Path.

- At 1180, retrace steps to car.

Blue Hills Reservation Map

Photo Album