The Great American Road Trip ChallengeOne trip, ~2.5 years, 48 states
New England

Stop 18 · Days 67–70

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. 67Day 67 — Rockwell & StockbridgeFull day · 4h 30m planned
  2. 68Day 68 — MASS MoCA & GreylockFull day · 5h planned
  3. 69Day 69 — Free DayFree day
  4. 70Day 70 — South to HartfordDrive day · 1h 10m drive

What this stop is made of

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