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 Sep 20: sunrise 6:29 AM · sunset 6:45 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 0.4 mi in (~10 min). Leave by 6:15 PM for the 6:45 PM sunset. Back at your car by 7:10 PM — 4 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
- East Head Pond–New Long Pond, 6 lakes 15.2 mi · ▲ 188 ft
- Tihonet Pond–East Head Pond, 6 lakes 15.8 mi · ▲ 321 ft
- Besse Bog Reservoir–Three Cornered Pond, 5 lakes 15.9 mi · ▲ 515 ft
- Jessup Road–Kamesit Road, 3 sights 6.6 mi · ▲ 193 ft
- Russell Millpond–Crosswinds Trail, 5 sights 14.6 mi · ▲ 674 ft
- Glen Charlie Pond–Besse Bog Reservoir, 5 lakes 15.3 mi · ▲ 551 ft
Get outside more
A wild hike near Cranberry Village, emailed to you once a week.
Hikes near Cranberry Village, Massachusetts