Route: Tri-State Tri-Mountain Loop (NY, CT, MA)

The Tri-State Tri-Mountain route takes you through some of the toughest terrain and climbing in southern New England, and is unique in that you pass through three states (Connecticut, New York, and Massachusetts) while covering several notable features along the way, including three significant summits and a state high point.

For the purpose of this FKT, the route begins at the trailhead of the Undermountain Trail off Route 41 in Salisbury, Connecticut. Climb up Undermountain and turn right onto Paradise Lane trail, looping around the base of Bear Mountain to reach the Appalachian Trail. From there run the connector trail to Mt. Washington Road and turn left, running another mile-plus to the trailhead for Brace Mountain on the right. Make your way along this trail, gradually climbing and hopping on a short out-and-back to reach the summit of Brace Mountain, at 2,311 feet the highest point in Dutchess County, New York. Be sure to soak in the views of the farmland below you and, in the distance, the Catskill Mountains in New York. Turning around, connect briefly with the Taconic Trail before dropping down to the Mt. Frissell Trail. From there reach the tri-state marker indicating where the borders of Connecticut, New York, and Massachusetts meet before climbing Mount Frissell. This section is unique; along the way to the actual 2,454-foot summit in Massachusetts, you reach the Connecticut high point on the southern slope at 2,379 feet. From Frissell drop quickly and steeply back down to Mt. Washington Road, passing Round Mountain on the way, and backtrack along the connector trail until you reach the Appalachian Trail again. From there, turn right (south) and climb to the summit of Bear Mountain, the highest peak in Connecticut at 2,232 feet, via the steep northern face. Continue over and down the southern slope of Bear Mountain, following the white blazes of the Appalachian Trail, to Riga Junction. Turn left back onto Undermountain Trail, and follow it back down to its trailhead and the start/finish. 

The Double Bear variation is an upgraded--slighter shorter but harder with more vertical gain per mile--version of the existing "Tri-State Tri-Mountain Loop". Instead of taking Paradise Lane around the base of Bear Mountain as with old route (thereby bypassing major ascent/climb up to Bear summit), new route takes the Appalachian Trail directly up to the summit and down the other side. On the way back, also running directly back up and down Bear Mountain. In essence, this is a double Bear Mountain ascent/descent that traverses the tri state tri mountain loop.