Driving Across Massachusetts

Driving across Massachusetts on the Oregon Trail road trip, we follow scenic Route 2, also known as the Mohawk Trail, traveling through the state’s northern tier, rather than US-20, which runs more or less underneath the Massachusetts Turnpike, I-90.

Map of the Oregon Trail for driving across Massachusetts.
Map of the Oregon Trail through Massachusetts.

Passing across some of the least populous and most deeply forested acres in the whole Commonwealth of Massachusetts, you can easily imagine you’re in Vermont rather than the so-called Bay State. Picking its way over the flattened summits of the Hoosac Range foothills to the Green Mountains in the north, Route 2 follows rock-strewn trout streams flecked with white water and shaded by boreal forests of hemlock, yellow birch, and red spruce—including some of the state’s only remaining stands of old growth.

Midway across Massachusetts, Route 2 bridges the Connecticut River above Turners Falls, lopes through the trees, and emerges at historic Lexington and Concord, at Boston’s back door.

Taking the Oregon Trail road trip route beyond Boston you’ll follow US-3 to Cape Cod.

Cape Cod Driving Tips

To avoid frustration and confusion when visiting Cape Cod, it helps to understand its basic directions and seasons. The compass isn’t your friend here, as you will discover when faced with highway signs stubbornly directing you south to Provincetown—when heading south would bring you sooner to Venezuela than to the Cape’s northernmost town. Instead, the principal directions are up and down: “Up-Cape” means generally westward, toward the mainland, while “Down-Cape” means roughly east, toward the Outer Cape and Provincetown. Further confusion arises with the distinctions among the various coasts: “Bayside” faces inward onto Cape Cod Bay, the “South Shore” faces Nantucket Sound, and the “Backside” braves the open Atlantic to the east.

Map of the Oregon Trail through Cape Cod.
Map of the Oregon Trail through Cape Cod.

It’s a little easier to keep track of Cape Cod’s seasons. High season, when Cape-bound traffic can be bumper-to-bumper from near Boston all the way to Hyannis, is basically from Memorial Day to Labor Day. The summer vacation months of July and August see the highest hotel rates, the most crowded beaches, and abysmal traffic on Fridays especially, when most vacation rentals “turn over.” That said, even at the worst of times you can still find peace and quiet if you’re willing to walk, paddle, or bike a little way from your car.

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