Plan with
Confidence
Path Type
Loop
This route begins and ends near the Notchview Reservation visitor center at 83 Old Route 9 in Windsor, MA, and follows a well-marked network of trails. The approximately 2-mile Circuit Trail forms the core loop through red spruce stands, northern hardwood forest, and occasional open meadows with limited views. From the trailhead, follow signage in an easterly direction for the Circuit Trail, staying on marked paths to avoid lesser-used or overgrown connectors. A gradual climb through quiet woods leads to mild elevation gain, with opportunities to spot wildlife along the way—this area is especially popular among bird-watchers.
Hikers can extend the route to explore other areas of the 3,000-acre property, including Judges Hill for a higher vantage. Open year-round, Notchview transitions into a groomed trail system for cross-country skiing and snowshoeing in winter. Hiking is still permitted during this season, but visitors should avoid ski tracks and follow posted rules. Dogs are allowed, with leash requirements from April 1 – August 15 and in designated ski areas. This moderate route offers a peaceful woodland experience and serves as a great introduction to the broader reservation.
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Ashuwillticook Rail Trail - Berkshire Mall Road to the town of Cheshire
Ashuwillticook Rail Trail - Berkshire Mall Road to the town of Cheshire
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