Hillside Pond & Headquarters Path (Blue Hills Reservation)

Hillside Pond & Headquarters Path (Blue Hills Reservation)

Hike Type: Out & Back with a side of spaghetti
Distance: 4.70 miles
Elevation: 348 feet
Time: 1 hour, 46 minutes
Hiking Challenges: Blue Hills 125-Mile Challenge (2x); 52 Hike Challenge

The Hike

Confession time: (to no surprise) I’ve fallen pretty behind on my journaling, and I’m reminding myself that that is okay! Last week was my “chorus-palooza” where I had a rehearsal, dress rehearsal, school-wide concert, and then a field trip to the Massachusetts State House all back-to-back, so my brain has been rather occupied. It’s currently May 31st, 2023 and I’m sitting in the Boston Public Library in Copley Square because I foolishly thought I could just walk into the RMV (why on earth does Massachusetts call it the RMV instead of the DMV?), but I couldn’t really go home because I walked to Forest Hills and need to be at Tufts for a lung function test at 12:30… so here I am! It’s actually beautiful in here and I wish I came here more often, but that’s a post for a different blog that does not yet exist. Onto the hike!

After my long jaunt in the Ossipees I wanted something a little more chill, and I still needed the Hillside Pond/Headquarters Path area, which perfectly fit my criteria! There was lots of poison ivy at the trailhead, which I am proud I was able to successfully identify! I started with the abysmal loop around Hillside Pond, which could really use some love. It’s such a beautiful area, but such a janky trail. It was decently buggy on this loop, but nothing biting. There were a couple guys fishing in different spots on the pond, which I haven’t seen before. We managed to avoid each other, which is a win for me! There was one random skull perched on a tree, though...

After the loop I took one of the unofficial trails to meet up with the trails behind the pond, and I couldn’t help but admire how the sun was shining through the overcast (which in reflection I think was actually haze from the Canadian wildfires), creating a lovely early golden hour. I also had a major win: successfully swatting at and killing a small bug! (I'm also now realizing that part of the yellow hue to all these photos is the pollen in the air...)

Back at Hillside Street, I crossed the road and continued my hike along the Border Path, paralleling Pine Tree Brook, which was fully covered in beautiful skunk cabbage. I took the out-and-back on Valley Path, which was uneventful, and saw my first tick at 1224! It was on a tall piece of grass reaching out its grimy paws looking to suck any innocent passerby’s blood. EVIL. 

The long out-and-back to Hartland Street was rather uneventful minus one snake, being constantly paranoid that the moles on my leg were ticks, and noticing a couple walking their dog on the private property through the woods. Oh, and at least 50,000 ant hills on the dike! 

I wrote in my notes “felt heavy and week today. ugh.” - but in reflection, that was most likely due to the physical abuse I put myself through a couple days prior. Progress isn’t linear! My final note for this hike was that I felt it was rude that this particular hike ends with an uphill, and I stand by that statement! All in all, I was able to get out, even if this hike didn’t give me the warm fuzzies, and that is okay!

Step-By-Step

- Park at Hillside Pond Parking on Hillside Strees.

- Start hike by hiking loop around Hillside Pond. 

- Near end of hike, turn right onto unmapped steep uphill path that connects to Barre Trail. 

- At terminus of unmapped trail, turn right onto Barre Trail. 

- Hike trails in this area, and then retrace steps to Barre Trail Trailhead on Hillside St.

- Cross Hillside St, continue hike on Border Path.

- At 1224, turn left onto Valley Path.

- At Chickatawbut Road, turn around.

- At 1224, continue straight/left onto Border Path.

- At 1215, continue to Unquity Road.

- At Unquity road, turn around.

- At 1215, turn left onto Massasoit Path.

- At terminus, turn around and retrace steps to Hillside St. 

Blue Hills Reservation Map

Photo Album