A classic Berkshire ride, starting from the Windflower Inn in Great Barrington, MA but very near the hamlet of South Egremont. It starts out with easy cycling along the flat flood plain of the Housatonic River through Sheffield farmland, then some gentle climbing toward Mill River, a Berkshire hill town, to Umpachenee Falls. On our return, we enjoy an exhilarating downhill ride back to the Housatonic River before returning to Sheffield, where you should stop by the oldest covered bridge in Massachusetts. This ride is approximately 33 miles.
Start: Windflower Inn, Rt. 23 E., Great Barrington, MA 01230 , near South Egremont
Distance: 33.3 mi Max Grade: 8.3 % Elevation: Gain and descent, 1262 ft
| Head southwest on MA-23 W/MA-41 S/S Egremont Rd from Windflower Inn | 0.0 mi |
| Slight left at Buttonball Ln | 0.4 mi |
| Turn left at Sheffield Egremont Rd | 0.5 mi |
| Continue onto Egremont Rd | 2.5 mi |
| Turn right at US-7 S/S Main St | 4.1 mi |
| Take the 1st right onto Cook Rd | 4.4 mi |
| Take the 1st left onto Miller Ave | 4.8 mi |
| Turn left to stay on Miller Ave | 4.9 mi |
| Turn right at US-7 S/S Main St | 5.6 mi |
| Turn left at Maple Ave | 5.7 mi |
| Slight right at Hewins St | 6.6 mi |
| Turn left at Polikoff Rd | 9.6 mi |
| Turn left at Sodom Rd | 12.2 mi |
| Slight left at Clayton Mill River Rd | 13.4 mi |
| Slight left to stay on Clayton Mill River Rd | 15.5 mi |
| Take the 1st right to stay on Clayton Mill River Rd | 18.3 mi |
| Take the 1st left onto Great Barrington Mill River Rd | 18.4 mi |
| Slight left at Mill River Great Barrington Rd | 18.9 mi |
| Take the 2nd left onto County Rd | 20.1 mi |
| Slight right at Boardman St | 24.8 mi |
| Turn left at Brookside Rd | 29.7 mi |
| Turn right at S Main St | 30.0 mi |
| Turn left at Silver St | 30.5 mi |
| Turn left at MA-23 W/MA-41 S/Maple Ave | 30.8 mi |
| Turn right to Windflower Inn across from Egremont Golf Club | 33.3 |
Bike New England 