AMBLEWAY Wildest hikes

Blue Hills Reservation

Kitchamakin Hill & Skyline Viewpoint via Skyline Trail

3.8 mi · ▲ 719 ft · 1 hr 38 min

Kitchamakin Hill & Skyline Viewpoint via Skyline Trail is a 3.8-mile out-and-back in Blue Hills Reservation near Milton, MA. The route passes Skyline Viewpoint and Kitchamakin Hill. It climbs 719 ft, with sections as steep as 31% grade, and is mostly dirt. It scores 2/100 on the Ambleway Wildness scale: paved and peopled.

Elevation

0 mi72 – 466 ft · steepest grade: 31%4.3 mi

Getting there

Trailhead: Unnamed 42.24034, -71.06949
Nearest town Milton, MA
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Directions

AMBLEWAYwww.ambleway.com

Kitchamakin Hill & Skyline Viewpoint via Skyline Trail

3.8 mi · ▲ 719 ft · 1 hr 38 min

Elevation 72–467 ft

Out & Back · Blue Hills Reservation

Trailhead: 42.24034, -71.06949

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

Transit-accessible: Randolph Ave and Highland St stop 15 m from the trailhead

  1. Start at the trailhead, heading E.
  2. 0.3 miBear right, heading E.
  3. 50 ftBear left, heading E.
  4. 0.3 miSharp right onto Headquarters Path, heading SW.
  5. 0.3 miBear left, heading SE.
  6. 250 ftBear right, heading SE.
  7. 250 ftBear right, heading SE.
  8. 0.1 miBear left, heading S.
  9. 0.2 miPass Skyline Viewpoint.
  10. 50 ftTurn left, heading S.
  11. 150 ftTurn right, heading SE.
  12. 50 ftBear right onto Skyline Trail, heading S.
  13. 50 ftTurn right, heading S.
  14. 50 ftPass Kitchamakin Hill.
  15. 150 ftTurn left, heading SE.
  16. 0.4 miReach Kitchamakin Hill, then turn around and head back the way you came.
  17. 0.5 miTurn right, heading NW.
  18. 100 ftBear left, heading N.
  19. 50 ftTurn left, heading N.
  20. 200 ftTurn right, heading NW.
  21. 0.2 miBear right, heading NW.
  22. 0.1 miBear left, heading N.
  23. 250 ftBear left, heading NW.
  24. 250 ftBear right onto Headquarters Path, heading N.
  25. 0.3 miSharp left, heading NW.
  26. 0.3 miBear right, heading NE.
  27. 50 ftBear left, heading W.
  28. 0.2 miArrive 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/kitchamakin-hill-out-back-5-km

Trail surface

76% dirt5% gravel19% unspecified

Weather

Sunrise 6:30 AMSunset 6:47 PM

Good to know

  • Transit-accessible: Randolph Ave and Highland St stop 15 m from the trailhead

Other ways to reach this destination

More from this trailhead

Hikes near Milton, Massachusetts