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

Wenakeening Woods–Pleasure Point, 3 beaches

10.6 mi · ▲ 94 ft · 3 hr 35 min

Wenakeening Woods–Pleasure Point, 3 beaches is a 10.6-mile out-and-back near Holliston, MA. The route passes Pleasure Point, Wenakeening Woods and Wenakeening Woods. It is mostly level, with 94 ft of elevation gain, and mostly gravel. It scores 0/100 on the Ambleway Wildness scale: paved and peopled.

Elevation

0 mi177 – 282 ft11.6 mi

Getting there

Trailhead: Upper Charles Trail 42.20407, -71.42169
Nearest town Holliston, MA
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Directions

AMBLEWAYwww.ambleway.com

Wenakeening Woods–Pleasure Point, 3 beaches

10.6 mi · ▲ 94 ft · 3 hr 35 min

Elevation 178–283 ft

Out & Back

Trailhead: Upper Charles Trail · 42.20407, -71.42169

Weather Sep 22: Overcast, high 64°F / low 51° · precip 3% · wind 8 mph · sunrise 6:34 AM · sunset 6:45 PM

Transit-accessible: Downtown Holliston stop 662 m from the trailhead · Parking lot at the trailhead

  1. Start on Upper Charles Trail, heading SW.
  2. 0.7 miPass Pleasure Point.
  3. 0.6 miPass Wenakeening Woods.
  4. 0.3 miPass Wenakeening Woods.
  5. 1 miContinue straight onto High Water Bypass, heading W.
  6. 0.2 miContinue straight onto Upper Charles Trail, heading SW.
  7. 1.2 miBear right, heading SW.
  8. 1.3 miTurn right, heading W.
  9. 150 ftTurn left, heading W.
  10. 0.3 miReach Wenakeening Woods, then turn around and head back the way you came.
  11. 0.3 miTurn left, heading E.
  12. 50 ftTurn right, heading E.
  13. 1.3 miBear right, heading NE.
  14. 1.2 miContinue straight onto High Water Bypass, heading NE.
  15. 0.2 miContinue straight onto Upper Charles Trail, heading NE.
  16. 2.2 miArrive back at the trailhead.

Each distance is the walk from the previous step. Tap a step for a map of its junction.

Trail map, photos and weather for this hike: www.ambleway.com/hikes/wenakeening-woods-wenakeening-woods-out-back-4-groves-18-km

Trail surface

73% gravel21% paved5% dirt1% unspecified

Weather

OvercastTemperature 64°F51°
Precip3%Wind8 mphUV6Humidity76%
Rained 0.2″ yesterday
Hourly temperature
65°50°
Sunrise 6:34 AM12 AM3 AM9 AM12 PM3 PM9 PMSunset 6:45 PM
Wed 63°47°
Thu 63°46°
Fri 68°46° 59%
Sat 70°50° 67%
Sun 62°56° 67%
Mon 62°56° 43%

Good to know

  • Transit-accessible: Downtown Holliston stop 662 m from the trailhead
  • Parking lot at the trailhead

Other ways to reach this destination

More from Upper Charles Trail Trailhead

Hikes near Holliston, Massachusetts