Myles Standish State Forest

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

0 mi108 – 233 ft10.7 mi

Getting there

Trailhead: connector 41.84846, -70.69314
Nearest town Cranberry Village, MA

Directions

AMBLEWAYwww.ambleway.com

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

  1. Start at the trailhead, heading NW.
  2. 50 ftTurn left onto Halfway Pond Road, heading W.
  3. 0.2 miSharp right onto Jessup Road, heading N.
  4. 0.6 miTurn right onto Three Cornered Pond Road, heading N.
  5. 0.5 miTurn left, heading E.
  6. 0.1 miTurn left, heading N.
  7. 50 ftTurn right, heading N.
  8. 0.2 miTurn left onto Sabbatia Road, heading SE.
  9. 0.4 miTurn left onto Torrey Pond Road, heading N.
  10. 50 ftTurn right onto Sabbatia Road, heading N.
  11. 0.5 miTurn right onto Federal Pond Road, heading N.
  12. 0.3 miTurn left onto Wayont Road, heading E.
  13. 0.9 miTurn right, heading NE.
  14. 0.6 miBear left, heading E.
  15. 0.8 miReach Crooked Pond, then turn around and head back the way you came.
  16. 0.8 miBear right, heading S.
  17. 1.5 miTurn right onto Federal Pond Road, heading S.
  18. 0.3 miTurn left onto Sabbatia Road, heading W.
  19. 0.5 miTurn left onto Torrey Pond Road, heading SW.
  20. 50 ftTurn right onto Sabbatia Road, heading SW.
  21. 0.4 miTurn right, heading S.
  22. 0.2 miTurn left, heading S.
  23. 50 ftTurn right, heading S.
  24. 0.1 miTurn right onto Three Corners Pond Road, heading NW.
  25. 0.5 miTurn left onto Jessup Road, heading W.
  26. 0.6 miSharp left onto Halfway Pond Road, heading S.
  27. 0.2 miTurn right, heading SE.
  28. 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

66% dirt34% unspecified

Weather

Light rainTemperature 78°F72°
Precip64%Wind5 mphUV7Humidity88%
Rained 0.2″ 3 days ago (0.4″ over the last week)
Hourly temperatureRain chance
80°70° 12 AM: 8% rain1 AM: 3% rain2 AM: 5% rain3 AM: 26% rain4 AM: 35% rain5 AM: 42% rain6 AM: 27% rain7 AM: 24% rain8 AM: 31% rain9 AM: 28% rain10 AM: 20% rain11 AM: 27% rain12 PM: 29% rain1 PM: 59% rain2 PM: 52% rain3 PM: 64% rain4 PM: 62% rain5 PM: 51% rain6 PM: 20% rain7 PM: 18% rain8 PM: 16% rain9 PM: 15% rain10 PM: 5% rain
Sunrise 5:39 AM12 AM3 AM9 AM12 PM3 PM6 PMSunset 8:00 PM
Tue 84°64°
Wed 83°64°
Thu 88°70°
Fri 97°72° 17%
Sat 93°71° 24%
Sun 95°72° 15%

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

More sunset hikes nearby

Good to know

  • Parking lot at the trailhead

Other ways to reach this destination

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