Hillside Pond & Chestnut Run Path
5.1 mi · ▲ 943 ft · 2 hr 10 min
Hillside Pond & Chestnut Run Path is a 5.1-mile out-and-back in Blue Hills Reservation near Milton, MA. The route reaches Hillside Pond. It climbs 943 ft, with sections as steep as 21% grade, and is mostly dirt. It scores 0/100 on the Ambleway Wildness scale: paved and peopled.
Elevation
0 mi184 – 466 ft · steepest grade: 21%6.2 mi
Getting there
Trailhead: Unnamed 42.22609, -71.05943
Nearest town Milton, MA
Directions
AMBLEWAYwww.ambleway.com
Hillside Pond & Chestnut Run Path
5.1 mi · ▲ 943 ft · 2 hr 10 min
Elevation 185–465 ft
Out & Back · Blue Hills Reservation
Trailhead: 42.22609, -71.05943
Weather Aug 4: Heavy rain, high 78°F / low 68° · precip 98% · wind 8 mph · sunrise 5:40 AM · sunset 8:03 PM
Parking lot at the trailhead
- Start at the trailhead, heading SE.
- 250 ftBear right, heading S.
- 300 ftTurn right, heading W.
- 0.1 miBear left, heading W.
- 200 ftTurn left, heading S.
- 100 ftTurn right, heading S.
- 300 ftTurn right, heading S.
- 300 ftTurn right, heading S.
- 0.8 miBear right, heading SW.
- 0.2 miBear right, heading SW.
- 350 ftBear right, heading S.
- 0.1 miBear right, heading W.
- 50 ftBear left, heading W.
- 200 ftPass Hillside Pond.
- 350 ftBear right onto Dark Hollow Path, heading W.
- 50 ftTurn right, heading W.
- 0.2 miBear left, heading S.
- 0.3 miBear right, heading W.
- 50 ftTurn left, heading W.
- 50 ftTurn right, heading W.
- 350 ftBear right, heading SW.
- 100 ftBear right, heading SW.
- 50 ftContinue straight onto North Skyline Trail, heading SW.
- 450 ftTurn right, heading SW.
- 0.3 miTurn right, heading NW.
- 250 ftTurn right onto Chestnut Run Path, heading N.
- 350 ftReach Hillside Pond, then turn around and head back the way you came.
- 350 ftTurn left, heading NE.
- 250 ftTurn left, heading N.
- 0.3 miTurn left onto North Skyline Trail, heading S.
- 0.1 miBear left, heading N.
- 50 ftBear left, heading SW.
- 400 ftTurn left, heading S.
- 50 ftTurn right, heading S.
- 50 ftBear left, heading S.
- 0.3 miBear right, heading SW.
- 0.2 miTurn left onto Dark Hollow Path, heading SE.
- 50 ftBear left, heading SE.
- 0.1 miBear right, heading NE.
- 50 ftBear left, heading NE.
- 0.1 miBear left, heading NE.
- 400 ftBear left, heading NE.
- 0.2 miBear left, heading E.
- 0.8 miTurn left, heading E.
- 300 ftTurn left, heading NE.
- 300 ftTurn left, heading NE.
- 100 ftTurn right, heading E.
- 200 ftBear right, heading NE.
- 0.1 miTurn left, heading NE.
- 300 ftBear left, heading E.
- 50 ftArrive back at the trailhead.
Each distance is the walk from the previous step. Tap a step for a map of its junction.
Trail surface
61% dirt5% gravel34% unspecified
Weather
Heavy rainTemperature 78°F68°
Precip98%Wind8 mphUV3Humidity74%
Rained 0.3″ 5 days ago
Hourly temperatureRain chance
80°65°
Sunrise 5:40 AM12 AM3 AM9 AM12 PM3 PM6 PMSunset 8:03 PM
Tue
81°63°
Wed
88°64°
Thu
86°70°
17%
Fri
94°73°
26%
Sat
88°72°
43%
Sun
95°72°
Good to know
- Parking lot at the trailhead
Other ways to reach this destination
More from this trailhead
- Nahanton Hill–Skyline Viewpoint Loop, 3 summits 1.7 mi · ▲ 208 ft
- Fenno Peak–Chickatawbut Hill, 6 summits 2.4 mi · ▲ 350 ft
- Little Dome–Blue Hills Reservation Viewpoint, 3 summits 2.4 mi · ▲ 207 ft
- Buck Hill Path 2.4 mi · ▲ 447 ft
- Hawk Hill Viewpoint & Hawk Hill Path via Bouncing Brook Path 2.8 mi · ▲ 405 ft
- Pakomet Spring–Blue Hills Reservation Viewpoint, 5 sights 3.5 mi · ▲ 199 ft
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Hikes near Milton, Massachusetts