Most cycling outfitters steer you toward Vermont’s country lanes, but western Massachusetts has a much denser network of roads, meaning more choices and less traffic. Base yourself at the Hotel Northampton downtown (doubles, $196), and get rentals from Northampton Bicycle (Cannondales available for $35 per day). Then pick from flat routes along the Connecticut River, a rolling century around Quabbin Reservoir, or farm-road rides that climb into the Berkshires—all of which will leave you wondering: Where are the cars? If you’ve got time for only one big ride, make it a 66-miler recommended by Patrick Brady, a cycling journalist and part-time guide. Head west out of Northampton on Route 143, turn south on Route 112, and head back to town on Route 66. Grab a fresh peach at Outlook Farm before a gentle descent into Northampton. Tip: don’t freak out if your paved road turns to dirt. The unpaved routes are super smooth around here; in fact, an annual 65-mile group ride called the Grand Fundo, Massachusetts’ answer to Italy’s famed Gran Fondo rides, includes 20 miles of dirt.
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