Pleasant Bay

Pleasant Bay Review

North of Chatham and on the way to Orleans, you'll encounter perhaps the most beautiful stretch of Route 28, the road that's so blighted by overdevelopment in Harwich, Dennis, and Yarmouth. Along here, the narrow road twists and turns alongside the western shoreline of rippling Pleasant Bay. Turn east onto any number of peaceful country roads, and you'll end up near the water and within view of Nauset Spit and Pleasant Bay's several islands. This is excellent biking and jogging territory—but keep in mind that Route 28 is fairly narrow along this span, with a tiny shoulder, so keep your eye out for oncoming traffic.