Crooked Pond–Jessup Road, 4 sights
10.1 mi · ▲ 415 ft · 3 hr 34 min
Crooked Pond–Jessup Road, 4 sights is a 10.1-mile out-and-back in Myles Standish State Forest near Cranberry Village, MA. The route reaches Crooked Pond at the turnaround, 5 miles in. It climbs 415 ft and is mostly dirt. It scores 70/100 on the Ambleway Wildness scale: backcountry feel.
Elevation
Getting there
Directions
Crooked Pond–Jessup Road, 4 sights
10.1 mi · ▲ 415 ft · 3 hr 34 min
Elevation 107–233 ft
Out & Back · Myles Standish State Forest
Trailhead: connector · 41.84846, -70.69314
Weather Aug 4: Light rain, high 78°F / low 72° · precip 64% · wind 5 mph · sunrise 5:39 AM · sunset 8:00 PM
Parking lot at the trailhead
- Start at the trailhead, heading NW.
- 50 ftTurn left onto Halfway Pond Road, heading W.
- 0.2 miSharp right onto Jessup Road, heading N.
- 0.6 miTurn right onto Three Cornered Pond Road, heading N.
- 0.5 miTurn left, heading E.
- 0.1 miTurn left, heading N.
- 50 ftTurn right, heading N.
- 0.2 miTurn left onto Sabbatia Road, heading SE.
- 0.4 miTurn left onto Torrey Pond Road, heading N.
- 50 ftTurn right onto Sabbatia Road, heading N.
- 0.5 miTurn right onto Federal Pond Road, heading N.
- 0.3 miTurn left onto Wayont Road, heading E.
- 0.9 miTurn right, heading NE.
- 0.6 miBear left, heading E.
- 0.8 miReach Crooked Pond, then turn around and head back the way you came.
- 0.8 miBear right, heading S.
- 1.5 miTurn right onto Federal Pond Road, heading S.
- 0.3 miTurn left onto Sabbatia Road, heading W.
- 0.5 miTurn left onto Torrey Pond Road, heading SW.
- 50 ftTurn right onto Sabbatia Road, heading SW.
- 0.4 miTurn right, heading S.
- 0.2 miTurn left, heading S.
- 50 ftTurn right, heading S.
- 0.1 miTurn right onto Three Corners Pond Road, heading NW.
- 0.5 miTurn left onto Jessup Road, heading W.
- 0.6 miSharp left onto Halfway Pond Road, heading S.
- 0.2 miTurn right, 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 0.6 mi in (~15 min). Leave by 7:25 PM for the 8:00 PM sunset. Back at your car by 8:30 PM — 1 min before dark. Car visible from the viewpoint
Good to know
- Parking lot at the trailhead
Other ways to reach this destination
More from connector Trailhead
- Halfway Pond Road 2.6 mi · ▲ 135 ft
- Barrett Pond via Dunham Road 3.2 mi · ▲ 85 ft
- Halfway Pond Road 3.3 mi · ▲ 135 ft
- Ryan Road & Shaw Road via Halfway Pond Road 3.6 mi · ▲ 84 ft
- West Line Road 3.7 mi · ▲ 83 ft
- Barrett Pond–Dunham Road Loop, 4 sights 4.1 mi · ▲ 136 ft
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