Easy to Moderate, 5.0 mi loop
1,086 ft elevation gain
Hiked 8/22/25
This trail starts by going to the highest point in Connecticut, which is higher than the highest peak (nearby Bear Mountain) on its way into both Massachusetts and then New York. Also joining up with the Appalachian trail for a bit before returning to CT its a refreshing hike great for check listers.
Farms along the valley west of Brace Mountain at sunset.
To the north of Brace Mountain lies Alander Mountain and Washburn Mountain behind it.
The state line between Massachusetts and Connecticut is delineated by this weathered brass marker, placed in 1906.
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