AMBLEWAY Wildest hikes

Blue Hills Reservation

Skyline Viewpoint–Kayla's Pond, 3 sights

5.3 mi · ▲ 255 ft · 1 hr 54 min

Skyline Viewpoint–Kayla's Pond, 3 sights is a 5.3-mile out-and-back in Blue Hills Reservation near Milton, MA. The route passes Kayla's Pond before reaching Skyline Viewpoint at the turnaround, 2.7 miles in. It climbs 255 ft. It scores 7/100 on the Ambleway Wildness scale: paved and peopled.

Elevation

0 mi105 – 246 ft6.0 mi

Getting there

Trailhead: Unnamed 42.24578, -71.05197
Nearest town Milton, MA
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Directions

AMBLEWAYwww.ambleway.com

Skyline Viewpoint–Kayla's Pond, 3 sights

5.3 mi · ▲ 255 ft · 1 hr 54 min

Elevation 105–245 ft

Out & Back · Blue Hills Reservation

Trailhead: 42.24578, -71.05197

Weather Aug 4: Overcast, high 85°F / low 63° · precip 0% · wind 8 mph · sunrise 5:40 AM · sunset 8:03 PM

Transit-accessible: Pleasant St @ Lawrence Rd stop 684 m from the trailhead

  1. Start at the trailhead, heading W.
  2. 100 ftBear left, heading SW.
  3. 0.3 miTurn right, heading NW.
  4. 250 ftBear right, heading NW.
  5. 0.4 miTurn left, heading W.
  6. 100 ftBear right, heading W.
  7. 0.6 miSharp right onto Headquarters Path, heading E.
  8. 0.4 miTurn left, heading S.
  9. 0.2 miSharp right, heading E.
  10. 0.6 miContinue straight onto Indian Camp Path, heading NE.
  11. 350 ftPass Kayla's Pond.
  12. 350 ftTurn left onto Skyline Trail, heading E.
  13. 150 ftReach Skyline Viewpoint, then turn around and head back the way you came.
  14. 150 ftTurn right onto Indian Camp Path, heading E.
  15. 0.7 miSharp left, heading W.
  16. 0.2 miTurn right onto Headquarters Path, heading NW.
  17. 0.4 miSharp left, heading NE.
  18. 0.6 miBear left, heading NW.
  19. 50 ftTurn right, heading NW.
  20. 0.4 miBear left, heading NE.
  21. 200 ftTurn left, heading E.
  22. 0.3 miBear right, heading S.
  23. 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/skyline-viewpoint-kaylas-pond-out-back-3-sights-9-km-d6fe

Trail surface

50% dirt26% paved24% unspecified

Weather

OvercastTemperature 85°F63°
Precip0%Wind8 mphUV8Humidity78%
Rained 0.4″ yesterday (0.6″ over the last week) · trails may be muddy
Hourly temperature
85°60°
Sunrise 5:40 AM12 AM3 AM9 AM12 PM3 PM6 PMSunset 8:03 PM
Wed 86°63°
Thu 87°71° 26%
Fri 95°73° 29%
Sat 89°73° 37%
Sun 95°72°
Mon 96°77° 15%

Sunset

The best sunset spot on this hike is 0.1 mi in (~1 min). Leave by 7:41 PM for the 8:03 PM sunset. Back at your car by 8:19 PM — 15 min before dark.

More sunset hikes nearby

Good to know

  • Transit-accessible: Pleasant St @ Lawrence Rd stop 684 m from the trailhead

Other ways to reach this destination

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Hikes near Milton, Massachusetts