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Bash-Bish Falls is an awesome Jump, and is the Highest Waterfall in Massachusetts. Parking below the falls at the Copake Falls Trailhead in NY & walking the easy hike. You start out in NY & half way up the trail you pass a sign welcoming you to Mass.
From East or West/MassPike (I-90): Take Exit 2 in Lee. Follow MA Rte. 102 west for 4.7 miles to Stockbridge. Turn left and follow U.S. Rte. 7 south for 7.7 miles through Great Barrington. Turn right and follow MA Rte. 23 west for 4.9 miles to South Egremont. Turn left onto MA Rte. 41 south, then take immediate right, Mount Washington Road; continue for 7.5 miles (becomes East St.). Turn right onto Cross Rd. then right onto West St. and continue for 1 mile. Turn left onto Falls Rd and follow for 1.5 miles to parking lot and trailhead on left.
From West, North and South/NY Rte. 22: Off NY Rte. 22 in Copake Falls take NY Rte. 344 east, past Taconic State Park, and park in the trailhead parking on the right. Or continue into Massachusetts (becomes Falls Rd.) for 2 miles. Parking lot and trailhead are on right.