Skyline Viewpoint & Kayla's Pond via Skyline Trail
5.6 mi · ▲ 460 ft · 2 hr 6 min
Skyline Viewpoint & Kayla's Pond via Skyline Trail is a 5.6-mile out-and-back in Blue Hills Reservation near East Milton, MA. The route passes Kayla's Pond before reaching Skyline Viewpoint at the turnaround, 2.8 miles in. It climbs 460 ft. It scores 6/100 on the Ambleway Wildness scale: paved and peopled.
Elevation
Getting there
Directions
Skyline Viewpoint & Kayla's Pond via Skyline Trail
5.6 mi · ▲ 460 ft · 2 hr 6 min
Elevation 76–245 ft
Out & Back · Blue Hills Reservation
Trailhead: 42.24202, -71.04940
Weather Sep 21: sunrise 6:30 AM · sunset 6:47 PM
Parking lot at the trailhead
- Start at the trailhead, heading N.
- 350 ftTurn left, heading W.
- 200 ftBear right, heading N.
- 50 ftTurn left, heading N.
- 200 ftTurn right, heading NW.
- 50 ftBear left, heading NW.
- 0.3 miTurn right, heading W.
- 250 ftBear right, heading NW.
- 0.4 miTurn left, heading NW.
- 100 ftBear right, heading W.
- 0.5 miTurn right, heading S.
- 50 ftTurn left, heading SE.
- 0.2 miTurn left, heading SE.
- 0.6 miSharp right, heading E.
- 0.6 miContinue straight onto Indian Camp Path, heading SE.
- 250 ftPass Kayla's Pond.
- 500 ftTurn left onto Skyline Trail, heading NE.
- 150 ftReach Skyline Viewpoint, then turn around and head back the way you came.
- 150 ftTurn right onto Indian Camp Path, heading E.
- 0.7 miSharp left, heading NW.
- 0.6 miTurn right, heading W.
- 0.2 miTurn right, heading W.
- 50 ftTurn left, heading W.
- 0.5 miBear left, heading NW.
- 50 ftTurn right, heading NW.
- 0.4 miBear left, heading NE.
- 250 ftTurn left, heading NE.
- 0.3 miBear right, heading NE.
- 50 ftTurn left, heading NE.
- 150 ftTurn right, heading E.
- 50 ftBear left, heading SE.
- 200 ftTurn right, heading S.
- 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 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.
Good to know
- Parking lot at the trailhead
Other ways to reach this destination
More from this trailhead
- Bouncing Brook Path–Headquarters Path, 3 sights 6.8 mi · ▲ 480 ft
- The Crags–Saint Moritz Pond, 4 lakes 6.7 mi · ▲ 571 ft
- Buck Hill Path & Headquarters Path 6.5 mi · ▲ 480 ft
- Headquarters Path 7.9 mi · ▲ 971 ft
- Headquarters Path 7.6 mi · ▲ 943 ft
- Headquarters Path 7.4 mi · ▲ 943 ft
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Hikes near East Milton, Massachusetts