Day Three: Wellfleet to Orleans
The first half of the ride is similar to Day Two, with hilly back roads winding through dense woods. But stay determined: The route eventually opens up to wide ocean views from atop a bluff overlooking LeCount Hollow Beach. When the road brings you back to sea level, take a breather and walk on the beach’s unusually white sand. After the break, pick up the Cape Cod Rail Trail, a 28-mile paved bikeway that follows a former railroad path. Lined with sandwich purveyors and ice cream shops, lots of scenic bridges, and the trip’s best fall foliage yet, the trail offers a tranquil (read: flat and impossible to get lost) alternative to biking along the road.