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

Stop 1 · Days 1–6

Boston

Boston, MA

Where the whole trip begins — colonial history, a ballgame at the oldest park in the majors, world-class museums, and a proper bowl of chowder.

Timing: Arrive late September so a Red Sox home game is still on the schedule before the regular season ends in early October.

Where to stay

  • The Omni Parker House

    Oldest continuously operating hotel in the country and birthplace of Boston cream pie, steps from the Freedom Trail.

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You gotta eat this

  • Clam chowder at Union Oyster House

    America's oldest restaurant, serving the New England classic since 1826.

  • A cannoli in the North End

    Mike's vs. Modern is Boston's eternal argument — settle it yourself.

The days here

Each day opens its own hour-by-hour page

  1. 1Day 1 — Freedom Trail & FenwayFull day · 7h 35m planned
  2. 2Day 2 — Harbor & the North EndFull day · 6h planned
  3. 3Day 3 — MuseumsFull day · 5h 30m planned
  4. 4Day 4 — Free DayFree day
  5. 5Day 5 — Beacon Hill & the Public GardenFull day · 5h planned
  6. 6Day 6 — CambridgeFull day · 4h 30m planned

What this stop is made of

  • Cities & Metros
  • Landmarks & Monuments
  • Museums & History
  • Outdoor & Water Activities
  • Sports & Gamedays
  • Food & Drink Trails
  • Guided Tours
  • Shopping