The Great American Road Trip ChallengeOne trip, ~2.5 years, 48 states
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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

87

Days

106

Things to do

6

States

The colour key

106 things to do across 87 days

  • Museums & History24
  • Outdoor & Water Activities20
  • Landmarks & Monuments18
  • Shopping9
  • Food & Drink Trails8
  • National Parks & Forests7
  • State Capitols6
  • Cities & Metros5
  • Skiing & Winter Sports2
  • Guided Tours2
  • Somber & Civil-Rights Sites1
  • Film & TV Locations1
  • Concerts & Venues1
  • Festivals & Events1
  • Sports & Gamedays1

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

Jump to a day

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

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 4PlymouthPlymouth, MADays 12–14

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

  3. Stop 6Nantucket & Martha's VineyardNantucket & Martha's Vineyard, MADays 20–23

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

  4. Stop 7PortsmouthPortsmouth, NHDays 24–26

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

  5. Stop 8KennebunkportKennebunkport, MEDays 27–29

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

  6. Stop 10AugustaAugusta, MEDays 35–37

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

  7. Stop 11Camden & the MidcoastCamden & the Midcoast, MEDays 38–41

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

  8. Stop 14ConcordConcord, NHDays 52–54

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

  9. Stop 16BurlingtonBurlington, VTDays 60–63

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

  10. Stop 17WoodstockWoodstock, VTDays 64–66

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

  11. Stop 18The BerkshiresThe Berkshires, MADays 67–70

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

  12. Stop 19HartfordHartford, CTDays 71–73

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

  13. Stop 20New HavenNew Haven, CTDays 74–76

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

  14. Stop 21MysticMystic, CTDays 77–79

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

  15. Stop 22ProvidenceProvidence, RIDays 80–83

    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.

  16. Stop 23NewportNewport, RIDays 84–87

    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.