Start at Mt. Anthony High School, heading east on County Street. Your first option to shorten the ride is at Buck Hill Road where you can cut over to 7A and back to Bennington. Otherwise, head north up East Road where it will become dirt at about 7.5 miles; the road is well-maintained and definitely rideable on a road bike. Again you can turn off to the right on Holy Smoke Rd or Trumbull Hill Road if you want to cut the ride short. East Road turns to Maple Hill Rd in Arlington (and it also turns back into pavement). You can follow 7A back to Bennington or if you want more dirt, take West Mt. Road into Shaftbury Hollow, which will loop you back to 7A. This is a pretty moderate route (although you could probably increase the difficult riding very hard), and it's a fantastic ride when the foliage starts to turn (as pretty much every ride in Vermont is that time of year).