Crystal Spring Loop, Doleful Pond, Healthy Heart Loop (Middlesex Fells Reservation)
Hike Type: Loop w/ spur, Loop, Little Loop
Distance: 5.09 miles
Elevation: 361 feet
Time: 1 hour, 43 minutes
Parking: Ample parking at Greenwood Park in Stoneham.
Hiking Challenges: 52 Hike Challenge 2026; Middlesex Fells Reservation
Hiking Challenges: 52 Hike Challenge 2026; Middlesex Fells Reservation
The Hike
I foolishly thought yesterday was hot. Today was HOT. 80 degrees! I was killing time while Christien was at work, so I fugred I'd get the trails in the Crystal Spring/Doleful Pond area of the Fells for the first time. Plan was loosely a double loop, first following the red Crystal Spring blazes and second following the green Healthy Heart trail.
The hike started through a really cute loosely zoo-themed playground and then I started to follow the red loop around! The trail passed a meadow restoration area and then followed a small little boardwalk around a swampy area that's drying up. I then broke my plan of following red blazes and hit the spur trail to Doleful Pond, since it was a one-way trail anyway. I was loving how green everything was, but not obsessed with the bugs or being able to feel the pollen.
At Gate 46, there was a backyard with dozens and dozens of birdhouses. I turned around and hiked to Gate 45, and enjoyed my time along the pond, which was more or less a murky pond that was 50% tall reeds. I did see a great blue heron flying away! There was a viewpoint that had two old stadium seats, which I found interesting.
Dolefiul Pond Road paralled a stone wall, turned right, and then followed people's back yard fences to the gate. This was a nice side trip! Now, back on task.
There was a nice breeze and I was SWEATY from the hot sun. Back on the Crystal Spring Trail, I climbed up Whip Hill on a more trail-like trail as the treetops were clanking in the breeze. Near the top of the hill, there was a sign discussing rogue trails and what students at Stoneham High School are doing to help, which was cool. I passed a few people, but soon remembered that hikers are NOT nearly as friendly here as they are in the Blue Hills. Thinking about it, I think it's partly because this side of the city runs more metropolitan, and also more people are here for "walking" versus "hiking."
After Whip Hill, the Crystal Spring trail descended slowly all the way to Crystal Spring, which had some cool stone structures and many flowers, including the common blue violet. There was no water flowing, but still cool to see! The trail climbed after this and turns right near the height of land. The forest floor here is dotted with common mayflowers pre-budding, which was really pretty.
Afterwards, the trail began to gradually climb up Saddleback Hill, which soon had a nice view over the road and to Spot Pond Reservoir. The wind was whipping! Afterwards, there were a couple more partial viewpoints, and then I was back at the playground!
I walked through the playground, which was more full of children this time around, probably because school was out. I started to follow the green blazes for Loop #2, but did hit the extra spur of Whip Hill Road before continuing on. The green blazes brought me around a wetland area and later made a few crossings with the Crystal Spring Trail. It circled an impressive boulder on the far side of the loop, and once near Saddleback Hill I checked the map and managed to get a stick in the eye... ugh...
Anyway, I soon finished that loop, and now it was time to just wander! I turned right at E2-2, hiked in towards some trails I hadn't hiked yet, past a wildly unphased deer, and then got the text that Christien was heading out, so it was time for me to head out, too!
Step-by-Step
Loop #1
- Park at Greenwood Park
- Start hike on red-blazed Crystal Springs Trail, clockwise.
- At E1-2, turn left.
- At E1-1, turn right onto Doleful Pond Road.
- At Gate 46, turn around.
- At Gate 45, turn around.
- At E1-1, turn right.
- At E1-2, turn left onto Crystal Springs Trail.
- Follow Crystal Springs Trail clockwise, hiking spur to Pond Street, then continuing.
- At E2-3, turn left onto trail.
- At Woodland Road, turn around.
- At E2-3, turn left onto trail.
Loop #2
- Back at Greenwood Park, start hike at same spot, following green Healthy Heart blazes.
- At E2-1, turn left onto Whip Hill Road
- At "NO TRESPASSING," turn around and follow green blazes clockwise.
- At E2-6, turn left.
- At E2-5, turn around.
- At E2-5, turn left.
Loop #3
- At E2-2, turn right.
- At E2-7, turn right.
- At E2-8, turn left.
- At F2-2, turn around.
- At E2-8, turn right onto Whip Hill Road.
- At E2-1, turn left and return to car.
Photo Album
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