The Great American Road Trip Challenge~4.5 years · 48 states · one loop
← New England

Stop 18 · Days 55–57

The Berkshires

The Berkshires, MA

Western Massachusetts' cultured hills — Norman Rockwell's studio, a giant contemporary-art mill, and the summer home of the Boston Symphony.

Where to stay

  • A Lenox or Stockbridge inn

    Gilded-Age 'cottages' turned country inns.

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You gotta eat this

  • A farm-to-table Berkshires dinner

    The hills are thick with excellent restaurants.

The days here

Each day opens its own hour-by-hour page

  1. 55Day 55 — Rockwell & StockbridgeFull day · 4h 30m planned
  2. 56Day 56 — MASS MoCA & GreylockFull day · 5h planned
  3. 57Day 57 — South to HartfordDrive day · 1h 10m drive

What this stop is made of

  • Museums & History
  • Outdoor & Water Activities
  • Concerts & Venues