Driving along the water down Winthrop Shore Drive or Shirley Street toward Deer Island, you could feel you have been warped to the Cape off-season — were it not for the low-flying planes en route to and from Logan International Airport. Unassuming, longstanding yacht clubs give way to winterized cottages, some dating to before the Great Depression, when Winthrop was a resort town for people working in Boston.
To explore Winthrop start along the water. Grab a snack at Winthrop Marketplace(35 Revere St., 617-846-6880, www.winthropmktplace.com) and head for Winthrop Shore Drive, which runs the short distance along Winthrop Beach. If it’s low tide, walk along parts of the beach; the shoreline affords some lovely views not only of the water but also of the town itself, including the looming red, white, and blue water tower. With summer still a few months off, you may have the beach to yourself. If you continue up Winthrop Shore Drive, you’ll hit the Highlands, where the town’s tonier homes are clustered; between some of the homes are more magnificent glimpses of the outer harbor.
Another good spot for a morning stroll is Deer Island, an island now in name only, since the channel separating it from the mainland was filled in by beach erosion during the Hurricane of 1938. Previously a Native American internment site, a quarantine station, and a prison, Deer Island today has a 2.6-mile pathway that curls around a state-of-the-art sewage plant — not an obvious tourist attraction, though the views of the harbor and the Boston skyline are magnificent. (Tours of the plant are given Tuesdays and Fridays, and can be arranged by calling 617-660-7607.)
