Hancock Hill–Hillside Pond, 5 lakes
10 mi · ▲ 1,028 ft · 3 hr 51 min
Hancock Hill–Hillside Pond, 5 lakes is a 10-mile out-and-back in Blue Hills Reservation near Five Corners, MA. The route passes Kayla's Pond, Hillside Pond and Hancock Hill before reaching ice pond at the turnaround, 4.9 miles in. It climbs 1,028 ft, with sections as steep as 34% grade, and is mostly dirt. It scores 8/100 on the Ambleway Wildness scale: paved and peopled.
Elevation
Getting there
Directions
Hancock Hill–Hillside Pond, 5 lakes
10 mi · ▲ 1,028 ft · 3 hr 51 min
Elevation 95–507 ft
Out & Back · Blue Hills Reservation
Trailhead: connector · 42.23025, -71.03207
Weather Aug 4: Overcast, high 84°F / low 64° · precip 0% · wind 8 mph · sunrise 5:40 AM · sunset 8:03 PM
Transit-accessible: Willard St opp Thistle Rd stop 102 m from the trailhead · Parking lot at the trailhead
- Start at the trailhead, heading NW.
- 200 ftTurn left onto Pipe Line, heading SW.
- 0.4 miPass Kayla's Pond.
- 50 ftBear left onto Indian Camp Path, heading NW.
- 0.8 miSharp left, heading W.
- 0.3 miTurn left onto Headquarters Path, heading W.
- 250 ftBear left, heading W.
- 0.6 miTurn left onto Red Dot Loop, heading SW.
- 350 ftTurn right, heading SW.
- 0.4 miBear right, heading SW.
- 0.2 miBear right, heading SW.
- 400 ftBear right, heading W.
- 0.1 miBear right, heading SW.
- 50 ftBear left, heading SW.
- 150 ftPass Hillside Pond.
- 400 ftBear right onto Dark Hollow Path, heading SW.
- 50 ftTurn right, heading SW.
- 0.2 miBear left, heading W.
- 0.3 miBear right, heading NW.
- 50 ftTurn left, heading NW.
- 50 ftTurn right, heading NW.
- 400 ftBear right, heading W.
- 50 ftBear right, heading W.
- 50 ftContinue straight onto North Skyline Trail, heading W.
- 0.1 miPass Hancock Hill.
- 0.1 miTurn right, heading SW.
- 0.2 miBear right onto Base Path, heading SW.
- 0.3 miBear left, heading NW.
- 0.3 miBear left, heading N.
- 0.1 miPass ice pond.
- 0.1 miBear left, heading NW.
- 450 ftReach Hancock Hill, then turn around and head back the way you came.
- 450 ftBear right, heading NW.
- 0.2 miBear right, heading N.
- 0.3 miBear right, heading NW.
- 0.3 miBear left, heading SE.
- 0.2 miTurn left onto North Skyline Trail, heading SW.
- 0.2 miBear left, heading SE.
- 100 ftBear left, heading SE.
- 350 ftTurn left, heading SE.
- 50 ftTurn right, heading SE.
- 50 ftBear left, heading SE.
- 0.3 miBear right, heading S.
- 0.2 miTurn left onto Dark Hollow Path, heading SW.
- 50 ftBear left, heading SW.
- 0.1 miBear right, heading S.
- 50 ftBear left, heading S.
- 0.1 miBear left, heading SW.
- 350 ftBear left, heading S.
- 0.2 miBear left, heading NE.
- 0.4 miTurn left onto Red Dot Loop, heading E.
- 350 ftTurn right, heading SE.
- 0.6 miBear left, heading E.
- 50 ftBear right onto Headquarters Path, heading E.
- 250 ftTurn right, heading E.
- 0.3 miSharp right, heading NE.
- 0.5 miContinue straight onto Indian Camp Path, heading N.
- 0.6 miContinue straight onto Pipe Line, heading E.
- 450 ftTurn right, heading NE.
- 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
Weather
Sunset
The best sunset spot on this hike is 2.1 mi in (~57 min). Leave by 6:46 PM for the 8:03 PM sunset. Back at your car by 9:10 PM, after dark — bring a headlamp.
Good to know
- Transit-accessible: Willard St opp Thistle Rd stop 102 m from the trailhead
- Parking lot at the trailhead
Other ways to reach this destination
More from connector Trailhead
- Rattlesnake Hill–Skyline Viewpoint Loop, 5 lakes 1.4 mi · ▲ 225 ft
- Saint Moritz Pond–Pipe Line, 3 sights 2 mi · ▲ 230 ft
- Q Wall–R Wall, 5 cliffs 2.3 mi · ▲ 232 ft
- Kayla's Pond & Headquarters Path 4.5 mi · ▲ 280 ft
- Kayla's Pond–Buck Hill Path, 3 sights 5.5 mi · ▲ 337 ft
- Houghton's Pond–Hillside Pond, 5 lakes 8.2 mi · ▲ 473 ft
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