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

← New EnglandBoston

Day02

Day 2 — Harbor & the North End — Boston

Full day6h planned

1Freedom Trail & Fenway 2Harbor & the North End 3Museums 4Free Day 5Beacon Hill & the Public Garden 6Cambridge 7Where the Revolution Began 8Salem 9Cape Ann 10Drive south to Plymouth 11Pilgrim Plymouth 12Drive to Cape Cod 13Hyannis & Kennedy country 14The National Seashore 15Provincetown 16Free / Beach Day 17Ferry to the Islands 18Nantucket 19Martha's Vineyard 20Back to the mainland, north to New Hampshire 21The Seacoast 22Up the coast to Kennebunkport 23Dock Square & the Point 24Into Portland 25Old Port & the Head Light 26Casco Bay 27Art & Food 28Inland to the capital 29The Capital on the Kennebec 30Back to the coast at Camden 31Camden Harbor & Mount Battie 32Rockland & Wyeth country 33Up the coast to Acadia 34Cadillac Sunrise & Park Loop 35Carriage Roads & Jordan Pond 36Schoodic & the sea 37Free Day 38Inland to the White Mountains 39Mount Washington 40Kancamagus & Franconia Notch 41Cannon & the Notch 42Free Day 43South to the capital 44The Capital 45West into Vermont 46Montpelier & Ben & Jerry's 47Stowe & Mount Mansfield 48Smugglers' Notch 49Down to the lake 50Church Street & the Waterfront 51Shelburne 52South to Woodstock 53Village & Farm 54South into the Berkshires 55Rockwell & Stockbridge 56MASS MoCA & Greylock 57South to Hartford 58Twain & the Atheneum 59Down to New Haven 60Yale & Apizza 61East along the shore to Mystic 62The Seaport & Aquarium 63Into Rhode Island 64RISD & College Hill 65Federal Hill & WaterFire 66Down to Newport 67The Breakers & the Cliff Walk 68Bellevue & Ocean Drive 69Leave New England for New York

The waterfront, the markets, and dinner in Little Italy.

10:00 AM – 11:30 AM· 1h 30m
Boston Harbor sightseeing cruiseGuided Tours
The skyline and harbor islands from the water — a relaxed way to read the city's geography.
66 Long Wharf, Boston, MA
12:00 PM – 2:00 PM· 2h
Faneuil Hall & Quincy MarketShopping
Historic marketplace with food stalls, street performers, and souvenir shopping.
4 S Market St, Boston, MA
6:00 PM – 8:30 PM· 2h 30m
Dinner in the North EndFood & Drink TrailsAnchor
Boston's Italian quarter — pasta, Paul Revere's house, and the cannoli showdown.
Hanover St, Boston, MA