Hillside Pond, Valley Path, Unquity Path (Blue Hills Reservation)

Hillside Pond, Valley Path, Unquity Path (Blue Hills Reservation)

Hike Type: Loopty Loops w/ Long Spur

Distance: 5.00 miles

Elevation: 413 feet

Time: 1 hour, 42 minutes

Parking: Parking on the side of Hillside Street on Hillside Pond side.
Hiking Challenges: 52 Hike Challenge 2026; Trail Trace the Blue Hills

The Hike 

It's definitely May. I was hiking in chilly mist yesterday, cold rain on Saturday, but today it's a HOT 75 degrees out! Back at the Blue Hills, the plan was to hike the Hillside Pond, Valley Path, and Unquity Path areas today. I started with the loop around Hillside Pond, which really is a lovely little loop. There were unfortunately small bugs out. There were fortunately turtles out, too! The path around the pond is always surprisingly rugged, and I like it. I did get a bug in my ear, though.

I was surprised by how clear the water in the pond was. I was equally surprised by the wild amount of water bugs that were swimming and scattering about. They were also comically clumsy. They acted like cartoon characters when startled: the just swamp into each other, bouncing off one another until they got away from the shore line. I was cooking in the sun, so I was happy that I wasn't doing an overly strenuous hike. 

I took an unmapped STEEP trail to hit the rest of the trails, and to mix things up I did some loopty loops, crossing Chickatawbut Road to avoid having to turn around - I liked it! I also loved the old stone walls in this area. I also did not love the multiple enormous piles of horse poop? The gnats were really out and about, as was the pollen. I did my loopty loops and continue on the Barre Trail past a great broken boulder and then I continued on down to Border Path, which is truly a delightful stretch of trail. It easily descends alongside a small stream, crossing it at the low point. The skunk cabbages were looking luscious as the treetops began to gain color. 

I continued up Valley Path and was delighted to see that I got the longer trail that goes through the Bermuda Triangle. I hit the small connector to Valley Path, the lower of the two had a massive blowdown to navigate. I hiked back down Valley Path, spooked a family of four deer (only three alerted their tails, though!), and then continued along the Border Path.

I passed the private land and fence gate with no connecting fense, and then hiked the border path to Unquity Road before continuing onto the Unquity Path. This stretch of the hike was expected feeling much longer than the rest... because it was. Part of the path was nearly overtaken with Japense Barberries, the swamp area was stinky, and the coniferous areas were beautiful with giant pinecones on the ground. 

Back "above ground," I was gateful that the grass wasn't too long yet, but I was sad the cars on Unquity Road were too loud for my Merlin Bird ID app to work well. I did decide to play Pokemon Go on the return trip, which was my saving grace! The return trip took me exactly 25 minutes of Pokemon Go. Time to head to Costco for chicken!

Step-by-Step

- Park at Hillside Pond.

- Start hike with a counter clockwise loop around Hillside Pond, hiking the second spur to the road.

- At the close of the loop, take the unmarked steep gravelly path east.

- Follow path.

- At terminus, turn right onto Barre Trail.

- At jct., stay right onto path towards Dark Hollow.

- At jct., turn right onto path.

- At terminus, cross Chickatawbut Road.

- Continue onto Headquarters Path.

- At jct., turn sharply left onto Quincy Path.

- At 2112, turn left onto Dark Hollow Path.

- At terminus, cross Chickatawbut Road.

- Continue on path on other side of road.

- At jct., turn right onto Headquarters Path.

- Cross Chickatawbut Road, continue on Headquarters Path.

- At jct., turn right onto Quincy Path.

- At jct., turn right onto Barre Trail.

- Cross Chickatawbut Road, continue on Barre Trail.

- Cross Hillside Street, continue on Border Path.

- At 1224, turn left onto Valley Path.

- At terminus, cross Chickatawbut Road, continue on path.

- At terminus at Hillside Street, turn around.

- Hike left spur, then return to Valley Path.

- At 1224, turn left onto Border Path.

- At Unquity Road, turn around.

- At 1215, turn left ono Unquity Path.

- At terminus, turn around and return to car.

Blue Hills Reservation Map

Photo Album