AMBLEWAY Wildest hikes
Upper Charles Rail Trail in Holliston May 2018 1.jpg
4300streetcar · CC BY 4.0

Wenakeening Woods–Lake Winthrop, 3 beaches

5.4 mi · ▲ 115 ft · 1 hr 51 min

Wenakeening Woods–Lake Winthrop, 3 beaches is a 5.4-mile out-and-back near Braggville Station, MA. The route passes Wenakeening Woods, Wenakeening Woods, Pleasure Point and Lake Winthrop before reaching Pleasure Point at the turnaround, 2.6 miles in. It is mostly level, with 115 ft of elevation gain, and mostly gravel. It scores 0/100 on the Ambleway Wildness scale: paved and peopled.

Elevation

0 mi184 – 269 ft5.9 mi

Getting there

Trailhead: Unnamed 42.17171, -71.46828
Nearest town Braggville Station, MA
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Directions

AMBLEWAYwww.ambleway.com

Wenakeening Woods–Lake Winthrop, 3 beaches

5.4 mi · ▲ 115 ft · 1 hr 51 min

Elevation 183–269 ft

Out & Back

Trailhead: 42.17171, -71.46828

Weather Aug 4: sunrise 5:43 AM · sunset 8:03 PM

Parking lot at the trailhead

  1. Start at the trailhead, heading SE.
  2. 300 ftTurn left onto Upper Charles Trail, heading NE.
  3. 0.5 miContinue straight onto High Water Bypass, heading NE.
  4. 0.1 miContinue straight onto Upper Charles Trail, heading NE.
  5. 50 ftContinue straight onto High Water Bypass, heading E.
  6. 150 ftContinue straight onto Upper Charles Trail, heading E.
  7. 0.8 miPass Wenakeening Woods.
  8. 0.4 miPass Wenakeening Woods.
  9. 0.3 miPass Pleasure Point.
  10. 350 ftBear right onto Cemetery Run, heading E.
  11. 0.2 miPass Lake Winthrop.
  12. 350 ftTurn left, heading SE.
  13. 50 ftBear left onto Pleasure Point Connector, heading SE.
  14. 450 ftPass Pleasure Point.
  15. 350 ftContinue straight onto Pleasure Point Access Road, heading N.
  16. 400 ftReach Wenakeening Woods, then turn around and head back the way you came.
  17. 0.1 miContinue straight onto Pleasure Point Connector, heading NE.
  18. 0.1 miBear right, heading S.
  19. 50 ftTurn right onto Cemetery Run, heading S.
  20. 0.3 miBear left onto Upper Charles Trail, heading N.
  21. 1.6 miContinue straight onto High Water Bypass, heading W.
  22. 150 ftContinue straight onto Upper Charles Trail, heading W.
  23. 100 ftContinue straight onto High Water Bypass, heading W.
  24. 0.1 miContinue straight onto Upper Charles Trail, heading W.
  25. 0.5 miTurn right, heading SW.
  26. 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 map, photos and weather for this hike: www.ambleway.com/hikes/pleasure-point-pleasure-point-out-back-11-km

Trail surface

73% gravel23% dirt4% unspecified

Weather

Sunrise 5:43 AMSunset 8:03 PM

Good to know

  • Parking lot at the trailhead

Other ways to reach this destination

More from this trailhead

Hikes near Braggville Station, Massachusetts