While US-7 gets the most tourist traffic, a more pastoral way south into Connecticut follows Route 41 via South Egremont, another of those well-preserved villages entirely ensconced in the National Register of Historic Places, which is hardly a rare honor in Massachusetts.
At the center of town, Mom’s Country Cafe (413/528-2414) is a friendly choice for a bite before or after a hike; you’ll find country breakfasts, burgers, pasta, and soups.
South Egremont also has a wonderful B&B inn, the Weathervane ($115 and up; 413/528-9580), which has 10 acres of gardens and grounds (including a swimming pool) and 10 rooms in a white clapboard farmhouse built in 1783.
South Egremont is the gateway to the state’s remotest corner, the 4,000 forested acres of Mount Washington State Forest. Within its wooded boundaries are miles of hiking trails, including a stretch of the Appalachian Trail climbing up to the 2,602-foot summit of Mt. Everett, but the highlight here is photogenic Bash Bish Falls, the highest in Massachusetts. A whopping 80-foot drop, splashing down in a V-shaped pair of cascades, Bash Bish Falls is no Niagara, but it’s a nice place to while away a hot summer’s afternoon.