AMBLEWAY Wildest hikes
Tunnel, Upper Charles Rail Trail, Holliston MA.jpg
John Phelan · CC BY-SA 4.0

Wenakeening Woods & Pleasure Point via Upper Charles Trail

3.5 mi · ▲ 68 ft · 1 hr 12 min

Wenakeening Woods & Pleasure Point via Upper Charles Trail is a 3.5-mile out-and-back near Holliston, MA. The route passes Pleasure Point and Wenakeening Woods before reaching Wenakeening Woods at the turnaround, 1.6 miles in. It is mostly level, with 68 ft of elevation gain, and mostly gravel. It scores 0/100 on the Ambleway Wildness scale: paved and peopled.

Elevation

0 mi177 – 256 ft3.6 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 via Upper Charles Trail

3.5 mi · ▲ 68 ft · 1 hr 12 min

Elevation 178–255 ft

Out & Back

Trailhead: Upper Charles Trail · 42.20407, -71.42169

Weather Aug 4: Overcast, high 82°F / low 62° · precip 0% · wind 5 mph · sunrise 5:42 AM · sunset 8:03 PM

Bikes allowed on the whole route · 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. 0.2 miReach Wenakeening Woods, then turn around and head back the way you came.
  6. 1.7 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-3-groves-7-km-4d09

Trail surface

99% gravel1% boardwalk

Weather

OvercastTemperature 82°F62°
Precip0%Wind5 mphUV7Humidity81%
Rained 1.1″ yesterday (1.5″ over the last week) · trails may be muddy
Hourly temperature
85°60°
Sunrise 5:42 AM12 AM3 AM9 AM12 PM3 PM6 PMSunset 8:03 PM
Wed 84°63°
Thu 89°70° 32%
Fri 96°72° 29%
Sat 93°70° 35%
Sun 96°68° 15%
Mon 94°72° 16%

Good to know

  • Bikes allowed on the whole route
  • 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