The Great American Road Trip Challenge~4.5 years · 48 states · one loop
← All regions

Leg 1 · Fall

New England

Foliage coast, lighthouse to ledge

New England

Tap a pin to open that stop's first day · numbers follow the driving order

The trip's opening act: colonial Boston, the Massachusetts coast and islands, the Maine coast and Acadia, the White Mountains and Green Mountains at peak foliage, the cultured Berkshires, and the Connecticut and Rhode Island shore.

Foliage rust and maple gold

Time it right

Open in Boston in late September to catch the Red Sox before the season ends, then ride the foliage north up the Maine coast and through the mountains as the leaves peak in early-to-mid October, working south through the Berkshires and Connecticut to close in Newport.

23

Stops

69

Days

100

Things to do

6

States

Jump to a day

Stops, in order

  1. Stop 2Lexington & ConcordLexington & Concord, MADay 7

    The 'shot heard round the world' — where the Revolution began — an easy half-hour from Boston, plus Thoreau's pond.

  2. Stop 3Salem & Cape AnnSalem & Cape Ann, MADays 8–10

    Witch-trial history and maritime fortunes in Salem, then the rocky artists' harbors of Cape Ann.

  3. Stop 4PlymouthPlymouth, MADays 11–12

    America's hometown — the Rock, the Mayflower, and a living-history village.

  4. Stop 6Nantucket & Martha's VineyardNantucket & Martha's Vineyard, MADays 18–20

    Two very different islands — Nantucket's whaling-era cobblestones and the Vineyard's gingerbread cottages and clay cliffs.

  5. Stop 7PortsmouthPortsmouth, NHDays 21–22

    New Hampshire's tiny, handsome seaport — colonial houses, a walkable brick downtown, and a lively food scene.

  6. Stop 8KennebunkportKennebunkport, MEDays 23–24

    A postcard Maine coastal village — Dock Square shops, a rocky point, and the Bush family compound.

  7. Stop 9PortlandPortland, MEDays 25–28

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

  8. Stop 10AugustaAugusta, MEDays 29–30

    Maine's small capital on the Kennebec — the State House, the governor's mansion, and the oldest surviving wooden fort in the country.

  9. Stop 11Camden & the MidcoastCamden & the Midcoast, MEDays 31–33

    'Where the mountains meet the sea' — a schooner harbor under Mount Battie, plus Rockland's Wyeth art and a classic lighthouse.

  10. Stop 14ConcordConcord, NHDays 44–45

    New Hampshire's compact capital — a working State House with legislators still in the original chambers, and a space-history museum.

  11. Stop 16BurlingtonBurlington, VTDays 50–52

    Vermont's lakefront college town — a pedestrian marketplace, Lake Champlain sunsets, and one of the country's best folk-art museums.

  12. Stop 17WoodstockWoodstock, VTDays 53–54

    The quintessential New England village — a covered bridge, a working 1890s farm, and a gorge nearby.

  13. Stop 18The BerkshiresThe Berkshires, MADays 55–57

    Western Massachusetts' cultured hills — Norman Rockwell's studio, a giant contemporary-art mill, and the summer home of the Boston Symphony.

  14. Stop 19HartfordHartford, CTDays 58–59

    Connecticut's capital — Mark Twain's whimsical mansion, the oldest public art museum in America, and a gold-domed statehouse.

  15. Stop 20New HavenNew Haven, CTDays 60–61

    Yale's Gothic campus, superb (free) museums, and the coal-fired apizza that starts fights among locals.

  16. Stop 21MysticMystic, CTDays 62–63

    A wooden-shipbuilding seaport frozen in the 1800s, a top aquarium, and the pizzeria that named a movie.

  17. Stop 22ProvidenceProvidence, RIDays 64–66

    Rhode Island's capital — a great art museum, an Ivy on a hill of colonial houses, Federal Hill's Little Italy, and rivers set on fire.

  18. Stop 23NewportNewport, RIDays 67–69

    The Gilded Age's summer capital — Vanderbilt 'cottages' on the cliffs, a legendary shore walk, and America's yachting history. New England's final stop before New York.