AMBLEWAY Wildest hikes
Upper Charles Rail Trail in Holliston May 2018 2.jpg
4300streetcar · CC BY 4.0

Lake Winthrop & Pleasure Point via Upper Charles Trail

2.5 mi · ▲ 54 ft · 52 min

Lake Winthrop & Pleasure Point via Upper Charles Trail is a 2.5-mile out-and-back near Holliston, MA. The route passes Pleasure Point and Lake Winthrop. It is mostly level, with 54 ft of elevation gain. It scores 0/100 on the Ambleway Wildness scale: paved and peopled.

Elevation

0 mi177 – 220 ft2.9 mi

Getting there

Trailhead: Unnamed 42.19922, -71.42534
Nearest town Holliston, MA
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Directions

AMBLEWAYwww.ambleway.com

Lake Winthrop & Pleasure Point via Upper Charles Trail

2.5 mi · ▲ 54 ft · 52 min

Elevation 178–220 ft

Out & Back

Trailhead: 42.19922, -71.42534

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 396 m from the trailhead · Drinking water at the trailhead · Parking lot at the trailhead

  1. Start at the trailhead, heading N.
  2. 100 ftSharp left onto Upper Charles Trail, heading SW.
  3. 0.4 miPass Pleasure Point.
  4. 0.3 miSharp left onto Cemetery Run, heading E.
  5. 0.2 miPass Lake Winthrop.
  6. 50 ftBear right, heading SE.
  7. 150 ftBear left, heading SE.
  8. 150 ftSharp right onto Cemetery Road, heading SE.
  9. 250 ftTurn left, heading SE.
  10. 0.1 miTurn left, heading SE.
  11. 200 ftSharp left, heading SE.
  12. 250 ftReach Lake Winthrop, then turn around and head back the way you came.
  13. 250 ftSharp right, heading S.
  14. 200 ftTurn right, heading SE.
  15. 0.2 miSharp left, heading N.
  16. 150 ftBear right, heading NW.
  17. 100 ftBear left onto Cemetery Run, heading NW.
  18. 0.3 miSharp right onto Upper Charles Trail, heading N.
  19. 0.7 miSharp right, heading NE.
  20. 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/lake-winthrop-out-back-3-km-35cd

Trail surface

52% gravel21% dirt1% boardwalk26% 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° 33%
Fri 96°72° 29%
Sat 93°70° 35%
Sun 96°68° 15%
Mon 94°72° 16%

Good to know

  • Transit-accessible: Downtown Holliston stop 396 m from the trailhead
  • Drinking water at the trailhead
  • Parking lot at the trailhead

Other ways to reach this destination

More from this trailhead

Hikes near Holliston, Massachusetts