Skyline Viewpoint & Headquarters Path
5 mi · ▲ 546 ft · 1 hr 56 min
Skyline Viewpoint & Headquarters Path is a 5-mile out-and-back in Blue Hills Reservation near Milton, MA. The route reaches Skyline Viewpoint at the turnaround, 2.5 miles in. It climbs 546 ft. It scores 1/100 on the Ambleway Wildness scale: paved and peopled.
Elevation
Getting there
Directions
Skyline Viewpoint & Headquarters Path
5 mi · ▲ 546 ft · 1 hr 56 min
Elevation 105–441 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
- Start at the trailhead, heading N.
- 50 ftBear right, heading N.
- 50 ftTurn left, heading NW.
- 200 ftTurn right, heading W.
- 50 ftBear left, heading W.
- 0.3 miTurn right, heading NW.
- 250 ftBear right, heading W.
- 0.4 miTurn left, heading W.
- 50 ftBear right, heading W.
- 0.6 miSharp right onto Headquarters Path, heading E.
- 0.4 miTurn right, heading SE.
- 0.3 miBear left, heading SW.
- 250 ftBear right, heading S.
- 250 ftBear right, heading S.
- 0.1 miBear left, heading SE.
- 0.2 miTurn left, heading SE.
- 100 ftReach Skyline Viewpoint, then turn around and head back the way you came.
- 50 ftTurn right, heading SE.
- 0.2 miBear right, heading S.
- 0.1 miBear left, heading N.
- 250 ftBear left, heading N.
- 0.3 miTurn right, heading NW.
- 0.4 miSharp left, heading NE.
- 0.6 miBear left, heading NW.
- 50 ftTurn right, heading NW.
- 0.4 miBear left, heading E.
- 250 ftTurn left, heading NE.
- 0.3 miBear right, heading S.
- 50 ftTurn left, heading SE.
- 200 ftTurn right, heading SE.
- 50 ftBear left, heading SE.
- 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 7.6 mi · ▲ 943 ft
- Headquarters Path 7.4 mi · ▲ 943 ft
- Hemenway Hill–Breakneck Ledge, 7 sights 9.2 mi · ▲ 805 ft
Get outside more
A wild hike near Milton, emailed to you once a week.
Hikes near Milton, Massachusetts