The Great American Road Trip Challenge~4.5 years · 48 states · one loop
← New EnglandPortland
Day25

Day 25 — Old Port & the Head Light — Portland

Full day4h planned
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1Freedom Trail & Fenway2Harbor & the North End3Museums4Free Day5Beacon Hill & the Public Garden6Cambridge7Where the Revolution Began8Salem9Cape Ann10Drive south to Plymouth11Pilgrim Plymouth12Drive to Cape Cod13Hyannis & Kennedy country14The National Seashore15Provincetown16Free / Beach Day17Ferry to the Islands18Nantucket19Martha's Vineyard20Back to the mainland, north to New Hampshire21The Seacoast22Up the coast to Kennebunkport23Dock Square & the Point24Into Portland25Old Port & the Head Light26Casco Bay27Art & Food28Inland to the capital29The Capital on the Kennebec30Back to the coast at Camden31Camden Harbor & Mount Battie32Rockland & Wyeth country33Up the coast to Acadia34Cadillac Sunrise & Park Loop35Carriage Roads & Jordan Pond36Schoodic & the sea37Free Day38Inland to the White Mountains39Mount Washington40Kancamagus & Franconia Notch41Cannon & the Notch42Free Day43South to the capital44The Capital45West into Vermont46Montpelier & Ben & Jerry's47Stowe & Mount Mansfield48Smugglers' Notch49Down to the lake50Church Street & the Waterfront51Shelburne52South to Woodstock53Village & Farm54South into the Berkshires55Rockwell & Stockbridge56MASS MoCA & Greylock57South to Hartford58Twain & the Atheneum59Down to New Haven60Yale & Apizza61East along the shore to Mystic62The Seaport & Aquarium63Into Rhode Island64RISD & College Hill65Federal Hill & WaterFire66Down to Newport67The Breakers & the Cliff Walk68Bellevue & Ocean Drive69Leave New England for New York

Wander the waterfront, then chase Maine's most famous lighthouse.

  1. 10:30 AM – 12:30 PM· 2h

    Explore the Old PortShopping

    Cobblestone streets of indie shops, roasters, and galleries — good for trinkets and souvenirs.

    Exchange St, Portland, ME

  2. 2:00 PM – 4:00 PM· 2h

    Portland Head Light & Fort Williams ParkLandmarks & MonumentsAnchor

    Commissioned by George Washington and standing since 1791 — the classic Maine postcard, with cliff walks around the fort.

    Bring: light jacket (coastal wind)

    12 Captain Strout Cir, Cape Elizabeth, ME