A charm in the harbor
In plain sight on its waterfronts (and from above), a small historic town thrives
You could spend much of your life in greater Boston and never venture into this small town dangling off Eastie into the harbor. Just over 1.6 square miles, it has no glitzy shopping complex, nor the orderly quaintness of Newburyport or even downtown Salem. Unless you live there, it’s out of the way, which is precisely its charm.
Getting here is a deliberate act. With just two roads leading in and out (one from East Boston, the other from Revere), chances are you won’t arrive by accident. Yet the town feels like an unexpected treat just the same.
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.)
If you are curious about Winthrop’s history, arrange a visit at the Deane Winthrop House (40 Shirley St., 617-846-8606, wihaonline.org/deane.html, $5 recommended donation), the house is the oldest continuously occupied wooden frame home in the country and the closest thing the town has to a museum. (Visits must be booked in advance.) Named for a son of John Winthrop, first governor of the Massachusetts Bay Colony, the oldest part of the house was built around 1637. Owned today by the Winthrop Improvement and Historical Association, it houses an assortment of artifacts: dinnerware, an old schoolhouse desk, slag from a copper smelting plant established by Paul Revere’s son Joseph in the 1840s, and old drawings and photographs of the town.
For a place its size, Winthrop has hosted its fair share of literary stars. In its day, the grand Taft’s Inn, which stood at what is now Maryland, Townsend, and Otis streets, near Deer Island, drew the likes of Ralph Waldo Emerson, Henry Wadsworth Longfellow, and Oliver Wendell Holmes. From 1936 to 1942, a young Sylvia Plath lived on Johnson Avenue, and had her first poem published while living there (in the Boston Herald, when she was 8). Years later, her short story “Superman and Paula Brown’s New Snowsuit’’ would recall her evenings watching the planes take off and land at Logan, across the harbor from her bedroom window. Plath devotees can visit the grave of her father, Otto, the subject of her famously tortured poem, “Daddy,’’ in Winthrop Cemetery. (The gravestone is in the cemetery’s lowest tier, near River Road.)
Head to the town center for lunch. Tiny, tidy, quiet, and slightly quirky, lined with awning-fringed, one-story businesses, the center feels both like a 1950s Pleasantville and a budding seaside arts community. Longtime establishments, including a pharmacy with paperbacks and a counter where folks can linger over coffee, and a shoe store that for decades has maintained a card catalog of customers’ shoe sizes, mingle with relative newcomers: a pet spa and boutique, a surf and skate shop, a Mexican and a Moroccan restaurant among them. The cafes include the friendly Moonstruck Gourmet & Cafe (47A Woodside Ave., 617-846-8866, www.moonstruckgourmet.com), which serves up homemade soups, panini, salads, and pastries, and sells fancy chocolates, teas, and work by local artists.
As in many towns, newcomers have brought a different flavor to the business landscape. The old and the new coexist well, says Cindy Levins, co-owner of the three-year-old Moonstruck and, two doors down, the 5 1/2-year-old Luna Boutique.
“Businesses run by people born and raised here have been very receptive to the newer ones,’’ says Levins, who moved to Winthrop from Cambridge about 18 years ago. “One of the things that strikes me is that the newer businesses have thrived, but the older businesses have, too.’’
If you’re in the mood to shop, in addition to Luna Boutique (3 Bartlett Road, 617-846-4644, www.lunaboutiqueonline.com), which sells jewelry, tableware, handbags, and bath and body products, there’s the small but charming Winthrop Book Depot & Cafe (11 Somerset Ave., 617-846-3099), which carries New York Times bestsellers, Oprah’s Book Club picks, paperback mysteries, and a sizable selection of children’s books and some games. Stitches by the Sea (66 Woodside Ave., 617-846-2195, www.stitchesbythesea.net) sells yarn, needlework supplies, and jewelry, and Katie’s Infants & Toddlers (32 Woodside Ave., 617-846-6010) sells clothing for little ones. (Some shops close early, so late morning or early afternoon is the best time to visit.)
If you prefer the outdoors, head to Belle Isle Marsh Reservation, site of Boston’s last remaining salt marsh. The park’s entrance is on Bennington Street in East Boston. The reservation is a peaceful oasis from the city, and a favorite spot for bird watchers (617-727-5350 or www.mass.gov/dcr/parks/metroboston/belleisle.htm). If you’re visiting between May and October, you can also arrange a kayak outing with Belle Isle Kayak Adventures, which offers marsh tours, Boston Harbor tours, kayak fishing, and other options tailored to interests and level of expertise. (Book tours a few days in advance. 617-719-2036 for hours and rates; www.belleislekayakadventures.com.)
If evening finds you still in town, head over to Cafe Rossetti’s (115 Winthrop Shore Drive, 617-539-9990), which serves superb Italian food in an unpretentious atmosphere. The restaurant, like some others in Winthrop, is BYOB; most entrees cost between $11.95 and $19.95. Or, if you’re heading out before dinner, first find a perch at the small Simon J. Donovan Beach on Pleasant Street, near the East Boston border, and engage in a local (and totally free) pastime, plane spotting.
Ami Albernaz can be reached at firstname.lastname@example.org.