Alander and Brace Mountains Loop Hike in the Southern Berkshires

If you’re looking for a long, scenic hike in the southern Berkshires with open summit views, a visit to three state borders, and a quieter backcountry feel, the Alander and Brace Mountains Loop is a great choice. This 13-mile loop travels through the Taconic Range near Millerton, New York, linking Brace Mountain, the New York–Massachusetts–Connecticut Tri-State Monument, and the broad summit of Alander Mountain.

The route is strenuous, with about 2,600 feet of elevation gain, but the effort is spread across a full day of steep climbs, rolling ridge walks, forest trails, old roadbeds, and open mountain terrain. It is not a quick hike, but it is one of the best longer loops in the southern Berkshires for hikers who want big views without the crowds of some of the region’s more popular destinations.

Alander and Brace Mountains Hike Summary

• Trailhead: Alander Brook Trailhead on Under Mountain Road near Millerton, New York

• Route: Alander Mountain Trail → Robert Brook Trail → South Taconic Trail → Brace Mountain → Mount Frissell Trail → Tri-State Monument → Ashley Hill Trail → Campground Trail → Alander Mountain Trail

• Distance: About 13 miles

• Elevation Gain: About 2,600 feet

• Difficulty: Strenuous

• Best For: Experienced hikers and prepared intermediate hikers looking for a full-day loop with open views and quiet trails

• Highlights: Brace Mountain, Alander Mountain, Tri-State Monument, ridge walking, historic fire observer cabin, and views toward the Hudson Valley and Catskills

Getting Started at Alander Brook

The hike begins at the Alander Brook Trailhead on Under Mountain Road. From the parking area, follow the Alander Mountain Trail for a short distance until reaching the junction with the Robert Brook Trail.

For this loop, turn right onto the Robert Brook Trail and hike counterclockwise. Going this direction saves the broad summit of Alander Mountain for later in the day, making it a great finish after a long stretch of ridge walking and forest travel.

The Robert Brook Trail begins climbing almost immediately. The route follows a ravine through the woods, gradually gaining elevation as it heads toward the South Taconic Trail. This is one of the more sustained climbs of the day, and while the trail is not overly technical, it is a steady uphill push that gets the legs working early.

Hiking Toward Brace Mountain

After reaching the South Taconic Trail, turn right and begin following the ridge toward Brace Mountain. The trail becomes more gradual here, with rolling terrain, scattered viewpoints, and a mix of open woods and stunted trees.

As you get closer to Brace Mountain, the landscape begins to open up. The forest thins in places, and views start to appear west toward the Hudson Valley and the Catskills.

Near the final approach to the summit, watch for an unsigned junction and turn right toward Brace Mountain. The summit is a worthwhile stop, with open ledges and wide views across the Taconic Range.

Brace Mountain is also the high point of Dutchess County, New York, giving the hike another fun landmark beyond the scenery.

Visiting the Tri-State Monument

From Brace Mountain, return to the South Taconic Trail and continue toward the Mount Frissell Trail. This section leads south toward one of the most unique features of the hike: the Tri-State Monument.

The monument marks the point where New York, Massachusetts, and Connecticut meet. It is a short side trip, but it is well worth making the stop. Standing at the marker gives the hike a little extra sense of adventure, especially after traveling across the long ridge from Brace Mountain.

After visiting the monument, return to the trail junction and follow the Ashley Hill Trail north toward Alander Mountain.

Through the Forest Toward Alander

The middle section of the loop has a quieter feel. The big open views are mostly behind you for now, and the route moves through forest trails and old roadbeds as it works its way back toward Alander Mountain.

This part of the hike is generally easier underfoot than the climb to Brace, but it still requires attention at several trail junctions. The route passes through a mix of trails, including the Ashley Hill Trail and Campground Trail, so a map or offline navigation is helpful.

There are a few streams and seasonal water sources in this area, but do not rely on them without carrying a filter. On a warm day, the distance, elevation gain, and exposed ridge sections can make water management especially important.

Climbing Alander Mountain

After reaching the Alander Mountain Trail, the route begins its final climb toward the summit. The trail gradually steepens as it rises through the forest, eventually passing the historic fire observer cabin just below the top.

The cabin is an interesting landmark and a reminder of the mountain’s past, but the real highlight is the summit just beyond it.

Alander Mountain has a broad, open summit that feels much bigger than the wooded approach suggests. The views stretch across the southern Berkshires, the Taconic Range, the Hudson Valley, and toward the Catskills. After a long day on the trail, it is an excellent place to stop, eat, rehydrate, and enjoy the reward before heading down.

Returning to Under Mountain Road

From the summit, follow the Alander Mountain Trail downhill toward the Alander Brook Trailhead. The upper section of the descent is steep and drops into the Alander Brook ravine, so take your time on wet leaves, mud, or loose rock.

Lower down, the trail follows easier old roadbed through the forest. Keep an eye on the final trail junctions near the bottom, and follow the blue-marked trail back toward the New York trailhead and Under Mountain Road.

The final miles feel much easier after the long day of climbing and ridge travel, but they are a welcome reminder that this is a full loop and not just a summit hike.

Why This Hike Is Worth It

The Alander and Brace Mountains Loop is one of the best longer hikes in the southern Berkshires because it offers so much variety. You get two memorable summits, big views, quiet woods, rocky ridge walking, a historic cabin, and the unique experience of standing at the meeting point of three states.

It is a demanding route, but it never feels repetitive. The steady climb to Brace, the open Taconic ridgeline, the Tri-State Monument, and the final summit of Alander all give the hike a different personality.

If you are looking for a strenuous but rewarding full-day hike near Millerton, New York, this loop deserves a place on your list.

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