Brace Mountain on the Taconic Ridge
Directions to trailhead
From NY Route 22 to Under Mountain Road (about 4 miles south of Route 344/Copake Falls). Park in the rail-trail parking area on the north side of the road and walk about half a mile to the trailhead; or drive just past the trailhead, around a sharp turn in the road to a small parking area on the left.
There are a number of great hiking options in the Taconics. You could, in fact, bag three states with a single hike in this area. (See one here.) This recommendation will get you two states, New York and Massachusetts, on an in-and-out hike of about 7 miles round-trip.
The route includes a strenuous climb to the ridge, though no rock scrambling, followed by an easy-to-moderate walk along a wide ridge-top woods road that eventually emerges above tree line to the treeless peak of Brace. An enormous cairn marks the summit, at 2304 feet, Dutchess County's highest point. Trails are often rocky, so good shoes/boots are recommended.
This is a great hike at any time of year, but when the colors of autumn splash across the landscape, it is especially fabulous.
Start at the Alander Brook trailhead on Under Mountain Road. In just 150 yards, turn right onto the red-blazed Robert Brook Trail. This trail climbs more than 1,000 feet in 1.1 miles, often paralleling the course of Robert Brook below.
At about the mile point, watch for a granite pillar that marks the boundary between New York and Massachusetts. The trail turns sharply left here, winding its way to a T-intersection with the South Taconic Trail. The entire length of the South Taconic Trail is close to 16 miles (white blazes); to the north it goes over Alander Mountain in Massachusetts (2250 feet in elevation). To head toward Brace Mountain, turn right (south) on the South Taconic.
As do many trails in the area, the South Taconic Trail follows the course of an old woods road. The distance from the Robert Brook Trail intersection to the summit of Brace is about 2.5 miles. The last mile or so is mostly above tree line and there are many outstanding views south, west, north, and a bit east. On a clear day look for Mount Greylock in Massachusetts.
From the summit, retrace your steps to complete a 7-mile hike or consult your trail map for other great options. Hint: take the side trail to Mount Frissell and you'll claim the highest point in Connecticut (it's not a summit, but the shoulder of Mount Frissell).