Begin at the Pilgrims’ settlement in Plymouth and follow Route 3 south to the Sagamore Bridge, an engineering marvel when it opened in 1935. Cross the bridge into Sagamore, where you can see artisans’ handiwork at Pairpoint Glass, the nation’s oldest glassworks; it opened in 1837.
In nearby Sandwich, the Cape’s oldest town, the Thornton W. Burgess Museum pays homage to its native son, who penned the classic children’s story The Adventures of Peter Cottontail.
Heading east on Route 6A, the road meanders through the quintessential Cape villages of Barnstable, Yarmouth, Dennis and Brewster. This area is known for hip boutiques and smooth beaches, and it’s dotted by weathered-shingled cottages, quaint bed-and-breakfasts and sprawling resorts. But you can still find freshwater ponds and lakes; there are several at Nickerson State Park in Brewster.
Cape Cod National Seashore
North of Orleans, Route 6 runs up the Outer Cape and the rugged fishing villages of Eastham, where you’ll find an entrance to the Cape Cod National Seashore. When Henry David Thoreau visited the shore of Cape Cod in the mid-1800s, he wrote that “A man may stand there and put all of America behind him.” A century later, President John F. Kennedy designated that same land as the Cape Cod National Seashore, which encompasses more than 44,000 acres of pristine beaches and marshland on the Commonwealth’s easternmost edge.
Farther up Route 6A, you’ll hit Wellfleet, where you’ll find the Wellfleet Bay Wildlife Sanctuary; and Truro, the breathtaking dunes of which are a timeless testament to the Atlantic Ocean’s relentless power and a must-see on any Cape Cod vacation.
With its windswept vistas and haunting light, Provincetown at the Cape’s northern tip has long been an inspiration to artists of every medium, including actors, writers and playwrights. Provincetown was the first spot where the Pilgrims landed. A commemorative 252-foot-high Pilgrim monument marks the event.