Lenox is a small town with a famous summer name. Tucked into the hills of the southern Berkshires, it grew in the nineteenth century into the place wealthy New Yorkers and Bostonians went to build enormous summer cottages, which they called cottages with a straight face. Edith Wharton built The Mount here in 1902, and wrote some of her best-known work while living on that hilltop. The big estates are mostly schools, inns and arts venues now, and the village centre is neat, white-steepled and a bit self-conscious, which is part of the charm.
Tanglewood, the summer home of the Boston Symphony Orchestra, is in Lenox, and on concert weekends the town fills with picnickers and the roads fill with cars. If you ride through between early July and the end of August, expect slow traffic around the evening hours and a hunt for parking. Otherwise this is quiet country. The roads out of town toward Lee, Stockbridge and West Stockbridge are the type that reward a loose schedule: gentle ups and downs, stone walls, hardwood forest crowding the shoulder, and little pull-offs by ponds and streams. The state forests nearby, October Mountain being the largest in Massachusetts, give you the sense of how big the woods really are. October Mountain is a forest of hemlock and hardwood that was once an estate belonging to a wealthy family before the state took it over.
Lenox itself has just under two thousand permanent residents, and the services are in keeping: a few cafes and restaurants, a handful of inns, and groceries, but for serious fuel and bigger shops, Pittsfield is ten minutes north and has everything. Lee, a little south, also has fuel and sits right by the Massachusetts Turnpike exit, which makes it a handy stop.
The riding season is long enough that it matters when you go. Summer brings the festival crowds and warm, humid air that smells of cut grass. Early autumn is the best of it, with cool mornings, mist in the valleys and the foliage building toward its peak. Spring has mud, frost heaves and the chance of a cold snap. If you can, take the back roads in the late afternoon, when the low light pushes through the trees and picks out the stone walls one by one.