In the very southwest corner of the state, near the New York state line, is Bash Bish Falls, the largest waterfall in Massachusetts. The water feeding the falls runs down a series of gorges before the torrent is sliced in two by a massive boulder perched directly above a pool. There it drops as a picture-perfect double waterfall. These 60ft-high falls are a popular spot for landscape painters to set up their easels.
A short, steep trail leads directly to the falls from the Massachusetts parking lot. For a gentler walk, continue driving 1 mile west across the state border to the New York parking lot, from where a more level path takes you to the water's edge. Hikes from both starting points take about 20 minutes each way.
To get there from Great Barrington, take MA 23 west to South Egremont. Turn onto MA 41 south and then take the immediate right onto Mt Washington Rd (which becomes East St) and continue for 7.5 miles. Turn right onto Cross Rd, then right onto West St and continue 1 mile. Turn left onto Falls Rd and follow that for 1.5 miles. The parking lot and trailhead will be on your left.