12 Best Small Towns for Weekend Getaways from Boston (2025)
Escape Boston to charming New England towns within 3 hours. From coastal Maine to Vermont mountains, discover perfect weekend destinations.
Published: 11/20/2025
Towns Featured in This Guide
Woodstock
Vermont•3,000 residents
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.
Stockbridge
Massachusetts•2,000 residents
Norman Rockwell's idealized America brought to life in the Berkshires. Main Street looks just like his famous painting, museum and all.