Weekend Getaways from Boston: 10 Charming Small Towns Within 3 Hours
Escape the city for a perfect New England weekend. Discover coastal villages, mountain retreats, and historic towns—all within an easy drive from Boston.
Published: 10/28/2025
Towns Featured in This Guide
Woodstock
Classic New England village with four covered bridges and spectacular fall foliage. Historic architecture meets farm-to-table dining in Vermont's most charming town.
Beaufort
Moss-draped Lowcountry gem where antebellum mansions overlook coastal waterways. Forrest Gump's bench and Pat Conroy's literary home.
Stockbridge
Norman Rockwell's idealized America brought to life in the Berkshires. Main Street looks just like his famous painting, museum and all.
Newport
Gilded Age opulence meets Atlantic waves along the legendary 3.5-mile Cliff Walk. Vanderbilt mansions and Jazz Festival by the sea.
Cape May
America's oldest beach resort with 600+ Victorian gingerbread houses. White sand beaches and painted lady B&Bs since 1620.