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

Stop 9 · Days 25–28

Portland

Portland, ME

New England's best small food city — a working waterfront, cobblestone Old Port, lighthouses, and lobster every which way.

Where to stay

  • The Press Hotel

    A boutique hotel in the former Portland Press Herald building — central to the Old Port.

    Open in Maps

You gotta eat this

  • Lobster roll at Eventide Oyster Co.

    The brown-butter lobster roll on a steamed bun that reset the standard.

  • A Holy Donut potato doughnut

    Maine potato in the dough makes them absurdly good.

The days here

Each day opens its own hour-by-hour page

  1. 25Day 25 — Old Port & the Head LightFull day · 4h planned
  2. 26Day 26 — Casco BayFull day · 3h planned
  3. 27Day 27 — Art & FoodFull day · 4h 30m planned
  4. 28Day 28 — Inland to the capitalDrive day · 1h 5m drive

What this stop is made of

  • Landmarks & Monuments
  • Museums & History
  • Outdoor & Water Activities
  • Food & Drink Trails
  • Shopping