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

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 Sep 20: Drizzle, high 62°F / low 49° · precip 48% · wind 2 mph · sunrise 6:30 AM · sunset 6:47 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 surface

50% dirt26% paved24% unspecified

Weather

DrizzleTemperature 62°F49°
Precip48%Wind2 mphUV1Humidity91%
Rained 1.7″ 7 days ago
Hourly temperatureRain chance
65°45° 3 AM: 1% rain4 AM: 2% rain6 AM: 7% rain8 AM: 4% rain9 AM: 3% rain10 AM: 4% rain11 AM: 5% rain12 PM: 17% rain1 PM: 32% rain2 PM: 43% rain3 PM: 43% rain4 PM: 48% rain5 PM: 22% rain6 PM: 32% rain7 PM: 14% rain8 PM: 20% rain9 PM: 15% rain10 PM: 19% rain11 PM: 26% rain
Sunrise 6:30 AM12 AM3 AM9 AM12 PM3 PM9 PMSunset 6:47 PM
Mon 64°57° 57%
Tue 58°53°
Wed 60°56°
Thu 60°56° 21%
Fri 61°55° 43%
Sat 56°54° 47%

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

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

Other ways to reach this destination

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