The Great American Road Trip ChallengeOne trip, ~2.5 years, 48 states
← New EnglandThe Berkshires
Day67

Day 67 — Rockwell & Stockbridge — The Berkshires

Full day4h 30m planned
123456789101112131415161718THE BERKSHIRES1920212223
1Freedom Trail & Fenway2Harbor & the North End3Museums4Free Day5Beacon Hill & the Public Garden6Cambridge7Where the Revolution Began8Salem9Cape Ann10Free Day11Drive south to Plymouth12Pilgrim Plymouth13Free Day14Drive to Cape Cod15Hyannis & Kennedy country16The National Seashore17Provincetown18Free / Beach Day19Ferry to the Islands20Nantucket21Martha's Vineyard22Free Day23Back to the mainland, north to New Hampshire24The Seacoast25Free Day26Up the coast to Kennebunkport27Dock Square & the Point28Free Day29Into Portland30Old Port & the Head Light31Casco Bay32Art & Food33Free Day34Inland to the capital35The Capital on the Kennebec36Free Day37Back to the coast at Camden38Camden Harbor & Mount Battie39Rockland & Wyeth country40Free Day41Up the coast to Acadia42Cadillac Sunrise & Park Loop43Carriage Roads & Jordan Pond44Schoodic & the sea45Free Day46Inland to the White Mountains47Mount Washington48Kancamagus & Franconia Notch49Cannon & the Notch50Free Day51South to the capital52The Capital53Free Day54West into Vermont55Montpelier & Ben & Jerry's56Stowe & Mount Mansfield57Smugglers' Notch58Free Day59Down to the lake60Church Street & the Waterfront61Shelburne62Free Day63South to Woodstock64Village & Farm65Free Day66South into the Berkshires67Rockwell & Stockbridge68MASS MoCA & Greylock69Free Day70South to Hartford71Twain & the Atheneum72Free Day73Down to New Haven74Yale & Apizza75Free Day76East along the shore to Mystic77The Seaport & Aquarium78Free Day79Into Rhode Island80RISD & College Hill81Federal Hill & WaterFire82Free Day83Down to Newport84The Breakers & the Cliff Walk85Bellevue & Ocean Drive86Free Day87Leave New England for New York

America's most beloved illustrator, at home in the Berkshires.

  1. 10:00 AM – 12:30 PM· 2h 30m

    Norman Rockwell MuseumMuseums & HistoryAnchor

    The world's largest collection of Rockwell's work, plus his relocated studio, in the town he painted.

    9 Glendale Rd, Stockbridge, MA

  2. 1:30 PM – 3:30 PM· 2h

    Tanglewood grounds & Stockbridge Main StreetConcerts & VenuesBonus

    Walk the summer home of the Boston Symphony (concerts in summer), then the Main Street Rockwell famously painted.

    297 West St, Lenox, MA

What the colours mean

On this day

  • Museums & History1
  • Concerts & Venues1

And how much each one matters

  • AnchorAlways do — the reason this stop is on the map
  • Worth itDo most of these
  • BonusQuirky bonus, if it's happening while you're here