Manchester is well-placed for exploring southwestern Vermont and the adjacent corners of New York and Massachusetts. The following destinations are all within 90 minutes.
Bromley Mountain (20 minutes north on Route 11) is a family-friendly ski area in winter and an adventure park in summer, with Vermont's longest alpine slide and a network of hiking trails on the summit. Smaller and less crowded than Stratton, it suits families with young children well.
Stratton Mountain (30 minutes east via Route 11/30) is the region's largest ski resort, with a full-scale village at the base and access to the Long Trail in summer. The Stratton Arts Festival in late September draws craftspeople and artists from across the region.
Dorset (15 minutes north on Route 30) is a quiet marble village — the stone was quarried here for the New York Public Library steps — with a famous summer theatre, the Dorset Theatre Festival, and a village green ringed by 18th-century buildings. Worth an hour on a quiet afternoon.
Bennington (30 minutes south on Route 7A) is the largest town in the region, with the Bennington Battle Monument, the Bennington Museum (strong on American folk art and the Grandma Moses collection), and a walkable historic downtown. A half-day is enough.
Woodstock (90 minutes north via US-4) is Vermont's most picture-perfect village — a covered bridge, elegant Federal houses, the Marsh-Billings-Rockefeller National Historical Park, and Billings Farm. It merits a full day if you make the drive.
Saratoga Springs, New York (80 minutes west via US-4) offers horse racing in summer, a lively downtown with good restaurants, the famous mineral springs, and the Saratoga Performing Arts Center. A full-day trip in racing season (July–August).