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
Directions
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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 Aug 4: Overcast, high 82°F / low 62° · precip 0% · wind 5 mph · sunrise 5:42 AM · sunset 8:03 PM
Transit-accessible: Downtown Holliston stop 662 m from the trailhead · Parking lot at the trailhead
- Start on Upper Charles Trail, heading SW.
- 0.7 miPass Pleasure Point.
- 0.6 miPass Wenakeening Woods.
- 0.3 miPass Wenakeening Woods.
- 1 miContinue straight onto High Water Bypass, heading W.
- 0.2 miContinue straight onto Upper Charles Trail, heading SW.
- 1.2 miBear right, heading SW.
- 1.3 miTurn right, heading W.
- 150 ftTurn left, heading W.
- 0.3 miReach Wenakeening Woods, then turn around and head back the way you came.
- 0.3 miTurn left, heading E.
- 50 ftTurn right, heading E.
- 1.3 miBear right, heading NE.
- 1.2 miContinue straight onto High Water Bypass, heading NE.
- 0.2 miContinue straight onto Upper Charles Trail, heading NE.
- 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 surface
73% gravel21% paved5% dirt1% unspecified
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
- 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
- Lake Winthrop & Pleasure Point via Upper Charles Trail 2.8 mi · ▲ 55 ft
- Wenakeening Woods & Pleasure Point via Upper Charles Trail 3.5 mi · ▲ 68 ft
- Upper Charles Trail 5 mi · ▲ 29 ft
- Upper Charles Trail 5 mi · ▲ 29 ft
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