Bennington County, VT combines classic New England charm and easy access to the Green Mountains—ideal for multi‑week stays with abundant hiking, biking, skiing, scenic drives, craft breweries and cozy farm‑to‑table dining. Small towns are walkable and relatively affordable, offering a quiet but culturally active base between shifts.
Within about 20–45 miles you can reach Pittsfield, MA (museums, galleries and restaurants) and Albany, NY (larger‑city dining, airport and cultural venues) for extra options.