AMBLEWAY Wildest hikes

Blue Hills Reservation

Hemenway Hill–Breakneck Ledge, 7 sights

9.2 mi · ▲ 805 ft · 3 hr 28 min

Hemenway Hill–Breakneck Ledge, 7 sights is a 9.2-mile out-and-back in Blue Hills Reservation near Milton, MA. The route passes Hillside Pond and Hemenway Hill before reaching Breakneck Ledge at the turnaround, 4.6 miles in. It climbs 805 ft. It scores 2/100 on the Ambleway Wildness scale: paved and peopled.

Elevation

0 mi105 – 476 ft10.8 mi

Getting there

Trailhead: Unnamed 42.24333, -71.05040
Nearest town Milton, MA
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Directions

AMBLEWAYwww.ambleway.com

Hemenway Hill–Breakneck Ledge, 7 sights

9.2 mi · ▲ 805 ft · 3 hr 28 min

Elevation 105–474 ft

Out & Back · Blue Hills Reservation

Trailhead: 42.24333, -71.05040

Weather Sep 20: sunrise 6:30 AM · sunset 6:47 PM

Parking lot at the trailhead

  1. Start at the trailhead, heading N.
  2. 50 ftBear right, heading N.
  3. 50 ftTurn left, heading NW.
  4. 200 ftTurn right, heading W.
  5. 50 ftBear left, heading W.
  6. 0.3 miTurn right, heading NW.
  7. 250 ftBear right, heading W.
  8. 0.4 miTurn left, heading W.
  9. 50 ftBear right, heading W.
  10. 0.6 miSharp right onto Headquarters Path, heading E.
  11. 0.4 miTurn right, heading SE.
  12. 0.3 miBear left, heading SW.
  13. 0.6 miTurn left onto Red Dot Loop, heading SW.
  14. 350 ftTurn right, heading SW.
  15. 0.4 miBear right, heading SW.
  16. 0.2 miBear right, heading SW.
  17. 400 ftBear right, heading W.
  18. 350 ftPass Hillside Pond.
  19. 150 ftBear right, heading SW.
  20. 50 ftBear left, heading SW.
  21. 0.1 miBear right onto Dark Hollow Path, heading SW.
  22. 50 ftTurn right, heading SW.
  23. 0.2 miBear left, heading SW.
  24. 0.3 miBear right, heading NW.
  25. 50 ftTurn left, heading NW.
  26. 50 ftTurn right, heading NW.
  27. 400 ftBear right, heading NW.
  28. 50 ftBear right, heading W.
  29. 50 ftContinue straight onto Wolcott Path, heading W.
  30. 0.2 miTurn right onto Breakneck Ledge Path, heading SW.
  31. 450 ftTurn left onto North Skyline Trail, heading SW.
  32. 150 ftPass Hemenway Hill.
  33. 450 ftPass Breakneck Ledge.
  34. 350 ftTurn right onto Jeffries Trail, heading NW.
  35. 450 ftReach Hemenway Hill, then turn around and head back the way you came.
  36. 450 ftTurn left onto North Skyline Trail, heading W.
  37. 0.2 miTurn right onto Breakneck Ledge Path, heading NE.
  38. 400 ftTurn left onto Wolcott Path, heading N.
  39. 0.2 miBear left, heading N.
  40. 100 ftBear left, heading N.
  41. 350 ftTurn left, heading S.
  42. 50 ftTurn right, heading S.
  43. 50 ftBear left, heading S.
  44. 0.3 miBear right, heading S.
  45. 0.2 miTurn left onto Dark Hollow Path, heading SE.
  46. 50 ftBear left, heading SE.
  47. 0.1 miBear right, heading E.
  48. 50 ftBear left, heading E.
  49. 0.1 miBear left, heading NE.
  50. 350 ftBear left, heading NE.
  51. 0.2 miBear left, heading NE.
  52. 0.4 miTurn left onto Red Dot Loop, heading NE.
  53. 350 ftTurn right, heading E.
  54. 0.6 miBear left, heading NE.
  55. 50 ftBear right onto Headquarters Path, heading NE.
  56. 0.3 miTurn right, heading N.
  57. 0.4 miSharp left, heading NE.
  58. 0.6 miBear left, heading N.
  59. 100 ftTurn right, heading NE.
  60. 0.4 miBear left, heading N.
  61. 250 ftTurn left, heading N.
  62. 0.3 miBear right, heading NW.
  63. 50 ftTurn left, heading NW.
  64. 200 ftTurn right, heading N.
  65. 50 ftBear left, heading N.
  66. 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 map, photos and weather for this hike: www.ambleway.com/hikes/hancock-hill-rattlesnake-hill-out-back-8-lakes-15-km-0878

Trail surface

53% dirt16% paved5% gravel26% unspecified

Weather

Sunrise 6:30 AMSunset 6:47 PM

Sunset

The best sunset spot on this hike is right at the trailhead, so there is no walk out. Be there by 6:27 PM to have the sun's last 20 minutes of sky before it sets at 6:47 PM. Your car is right there — dark at 7:15 PM.

More sunset hikes nearby

Good to know

  • Parking lot at the trailhead

Other ways to reach this destination

More from this trailhead

Hikes near Milton, Massachusetts