Edwin G. Bennett Airport

Small-town charm along the Housatonic River in the Berkshires.

Sheffield is a quiet, historic town in Berkshire County, southwestern Massachusetts, nestled along the Housatonic River and bordered by rolling hills and farmland. Founded in 1733, it holds the distinction of being the oldest town in Berkshire County and carries a rich Colonial and Revolutionary War heritage.

Visitors come for antique shops, covered bridges, and access to outdoor recreation in the surrounding countryside. The town serves as a peaceful base for exploring the wider Berkshires region, with Tanglewood, Mass MoCA, and the Appalachian Trail all within easy reach.

• •Ashley House — one of the oldest Colonial homes in the Berkshires, tied to a landmark slavery legal case.
• •Sheffield Covered Bridge — a charming 19th-century bridge, one of the last remaining in Massachusetts.
• •Bartholomew's Cobble — a nationally designated natural landmark with rare plants and scenic riverside trails.
• •Appalachian Trail Access — hike stunning ridgelines through Berkshire County farmland and forest.
• •Race Brook Falls — a popular short hike leading to a beautiful multi-tiered waterfall.
• •Local Antique Shops — Sheffield's main street is renowned as an antique-hunting destination.

Getting around: Sheffield has no public transit of its own; a personal vehicle is essentially required. The nearest Amtrak service is in Pittsfield, about 20 miles north. Rideshare availability is limited in this rural area, so renting a car before arrival is strongly recommended.

Best time: Late September through mid-October offers spectacular fall foliage, while June through August brings warm weather ideal for hiking and outdoor events.

Local food: Look for farm-fresh produce at local stands, maple syrup from nearby sugarhouses, and classic New England comfort food at country inns and diners throughout the Berkshires.

This guide is provided for general information only. Verify details locally before making travel decisions.