Skyline Viewpoint & Headquarters Path
4.7 mi · ▲ 532 ft · 1 hr 50 min
Skyline Viewpoint & Headquarters Path is a 4.7-mile out-and-back in Blue Hills Reservation near Milton, MA. The route reaches Skyline Viewpoint at the turnaround, 2.3 miles in. It climbs 532 ft, with sections as steep as 18% grade, and is mostly dirt. It scores 0/100 on the Ambleway Wildness scale: paved and peopled.
Elevation
Getting there
Directions
Skyline Viewpoint & Headquarters Path
4.7 mi · ▲ 532 ft · 1 hr 50 min
Elevation 54–486 ft
Out & Back · Blue Hills Reservation
Trailhead: 42.23553, -71.06917
Weather Sep 21: sunrise 6:31 AM · sunset 6:45 PM
Transit-accessible: Randolph Ave @ Ridgewood Rd stop 36 m from the trailhead
- Start at the trailhead, heading NE.
- 0.2 miSharp right, heading SE.
- 0.2 miBear right, heading E.
- 50 ftBear left, heading E.
- 0.3 miSharp right onto Headquarters Path, heading SW.
- 0.3 miBear left, heading S.
- 0.6 miTurn left onto Red Dot Loop, heading SW.
- 350 ftTurn right, heading S.
- 0.3 miTurn left, heading SW.
- 0.3 miBear left onto Buck Hill Path, heading S.
- 50 ftTurn right, heading S.
- 100 ftTurn left, heading S.
- 250 ftTurn left, heading S.
- 50 ftTurn right, heading S.
- 50 ftReach Skyline Viewpoint, then turn around and head back the way you came.
- 100 ftTurn left, heading S.
- 50 ftTurn right, heading S.
- 250 ftTurn right, heading S.
- 150 ftBear right, heading S.
- 0.3 miTurn right, heading NW.
- 0.3 miTurn left onto Red Dot Loop, heading NW.
- 350 ftTurn right, heading NE.
- 0.6 miBear left, heading NE.
- 50 ftBear right onto Headquarters Path, heading NE.
- 0.3 miSharp left, heading NE.
- 0.3 miBear right, heading N.
- 50 ftBear left, heading N.
- 0.2 miSharp left, heading W.
- 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 surface
Weather
Sunset
The best sunset spot on this hike is 1.4 mi in (~42 min). Leave by 5:44 PM for the 6:45 PM sunset. Back at your car by 7:36 PM, after dark — bring a headlamp.
Good to know
- Transit-accessible: Randolph Ave @ Ridgewood Rd stop 36 m from the trailhead
Other ways to reach this destination
More from this trailhead
- Crags Foot Path–Old Furnace Brook Path, 3 sights 5 mi · ▲ 298 ft
- Bouncing Brook Path–Headquarters Path, 3 sights 4.8 mi · ▲ 260 ft
- M Wall–Crags Foot Path, 3 sights 5.4 mi · ▲ 300 ft
- Q Wall–R Wall, 5 cliffs 5.3 mi · ▲ 300 ft
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Hikes near Milton, Massachusetts