Lake Winthrop & Pleasure Point via Upper Charles Trail is a 2.8-mile out-and-back near Holliston, MA. The route passes Pleasure Point before reaching Lake Winthrop at the turnaround, 1.3 miles in. It is mostly level, with 55 ft of elevation gain, and mostly gravel. It scores 0/100 on the Ambleway Wildness scale: paved and peopled.
Elevation
0 mi177 – 220 ft3.0 mi
Getting there
Trailhead: Upper Charles Trail 42.20407, -71.42169
Nearest town Holliston, MA
Directions
AMBLEWAYwww.ambleway.com
Lake Winthrop & Pleasure Point via Upper Charles Trail
2.8 mi · ▲ 55 ft · 58 min
Elevation 178–220 ft
Out & Back
Trailhead: Upper Charles Trail · 42.20407, -71.42169
Weather Sep 20: sunrise 6:32 AM · sunset 6:48 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.
- 0.3 miSharp left onto Cemetery Run, heading E.
- 0.3 miTurn left, heading SE.
- 50 ftBear left onto Pleasure Point Connector, heading SE.
- 500 ftReach Lake Winthrop, then turn around and head back the way you came.
- 0.1 miBear right, heading NE.
- 50 ftTurn right onto Cemetery Run, heading NE.
- 0.3 miSharp right onto Upper Charles Trail, heading NW.
- 1 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
72% gravel27% dirt1% boardwalk
Weather
Sunrise 6:32 AMSunset 6:48 PM
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
- Wenakeening Woods–Pleasure Point, 3 beaches 10.6 mi · ▲ 94 ft
- Upper Charles Trail 5 mi · ▲ 29 ft
- Upper Charles Trail 5 mi · ▲ 29 ft
- Wenakeening Woods & Pleasure Point via Upper Charles Trail 3.5 mi · ▲ 68 ft
Get outside more
A wild hike near Holliston, emailed to you once a week.
Hikes near Holliston, Massachusetts