Cape May vs. Sag Harbor

© Joyce Lee

Two seeming geographic antagonists, Cape May, on the Jersey Shore's southern tip, and Sag Harbor, on the northern edge of New York's north fork, have more in common with each other than with their amped up surroundings.

Though they share an ocean, and geographical proximity, it’s hard to imagine two summer resort communities less alike than the Jersey Shore and the Hamptons. Do I really need to spell this out? Tattoo parlors, Budweiser, and flip-flops versus SoulCycle, Domaines Ott rosé, and espadrilles. Clambakes versus movie premieres. Miniature golf courses versus grass tennis courts. And yet, improbably enough, there are two towns at the edge of each of these iconic American summer retreats that share DNA and summer visitors; towns that are, if not quite sister communities, then cousins: Cape May and Sag Harbor.

A former whaling com
munity on Peconic
 Bay settled in the early
 1700s, Sag Harbor
has always seemed a little 
removed from the flashy 
frenzy of the Hamptons—
those oceanside villages that 
have for more than a cen
tury served as summer colonies to Manhattan’s wealthi
est and most fashionable
residents. Sag Harbor was 
one of the busiest ports on 
the East Coast in the 18th 
century, a raffish town that
 scandalized the sensibilities 
of Moby Dick ’s Queequeg. 
It’s less polished than East
 Hampton or Southampton,
 more middle-class and blue-collar than its upscale neighbors, with anachronisms like a five-and-dime store, the American Legion Hall, and the barber-shop-cum-salon on Main Street—there is no beach!

Cape May, also a former whaling town, sits at the southernmost tip of the Jersey Shore, on a peninsula between Delaware Bay and the Atlantic, and was for much of the 19th century the summer destination of some of the political and social elite of Washington, D.C., Philadelphia, and Baltimore. With its stock of pastel-colored Victorian houses, it can feel a world away from the motels and boardwalk amusement parks of nearby communities like Wildwood and Asbury Park.

Both towns can give the visitor the sense of having stepped into a time warp. Despite the fires that ravaged Sag Harbor’s Main Street throughout the years, dozens of 18th- and 19th-century houses remain, including those built for whaling captains, the town’s most prominent citizens during its period of greatest prosperity. Sag Harbor’s fortunes dipped when the whaling industry collapsed in the late 1840s, with many of the whaling ships departing for the West Coast during the gold rush, and the discovery of petroleum in Pennsylvania sealed the end of the whaling era.

Cape May thrived through most of the 19th century as a summer resort, and when much of the town burned in the fire of 1878, it was rebuilt in the style of the day as a village of late-Victorian gingerbread houses, much of which has survived down to the present. After the turn of the century, the summer crowds largely bypassed the peninsula for more easily accessible spots along the coast; in Cape May, as in Sag Harbor, a long period of economic stagnation helped preserve the town’s historic buildings. Both towns have a penchant for street festivals that are either quaint or hokey, depending on your point of view, like the HarborFest, which takes place in Sag Harbor in September and includes clamshucking and beard-growing contests and a whale-boat race. Cape May celebrates local agriculture with a tomato festival, a strawberry festival, and, yes, a lima bean festival. Every Halloween, Main Street in Sag Harbor becomes a teeming twilight boulevard of young ghosts, witches, and princesses collecting candy from the local stores.

Fashion designer Nicole Miller, who grew up in the Berkshires and now has a summer home in Sag Harbor, spent childhood summers on Cape May. “I always loved the boardwalk,” she says. “It was very low-key—it never had roller coasters and rides like other ocean- front resorts. Just Skee-Ball, miniature golf, ice cream cones, and saltwater taffy. We always stayed in Cape May Point, where my grandmother had a house near the duck pond. We loved to walk down to the ocean first thing when we arrived to see what had happened over the winter.” Miller returned last summer, with a group of Hamptonites, after a long absence and was happily surprised to find Cape May Point much as she remembered.

I first visited Cape May Point in 2002, when a friend invited me to the reopening of Congress Hall (rooms from $200; 200 Congress Pl., Cape May; 609-884-8421;, an oceanfront hotel that opened its doors in 1816, when the whaling town was beginning to attract summer visitors, and had become hugely popular by the mid-19th century. Presidents Franklin Pierce, James Buchanan, Ulysses S. Grant, and Benjamin Harrison made it their summer retreat. I was impressed by the meticulous restoration of the hotel and also by the time-capsule quality of the town itself. Even the mid-century motels had a certain quaint, dated charm. As a summer denizen of the Hamptons, I felt like I’d stepped into a sort of prelapsarian Pleasantville, where the houses and the saltwater taffy came in Technicolor. Fudge, ice cream, and waffles seemed to be the principal foodstuffs.

I’d been invited to the re-
opening of the hotel by 
Curtis Bashaw, a genial entrepreneur with leading-
man looks, who was responsible for rescuing and
 renovating the colonnaded landmark. Bashaw had grown up spending his summers in Cape May, where his maternal grandfather, evangelist reverend Carl McIntire, led the Cape May Bible Conference at Congress Hall from 1968 to 1995, thus preserving the historic structure at a time when some of Cape May’s landmarks were being abandoned and demolished.

“I had this kind of Eloise childhood,” Bashaw says, “growing up in these big, old hotels that my grandfather bought for almost nothing.” He observed the first wave of revival in the ‘70s, when the town elected an expatriate preservationist mayor. “All these New Yorkers adopted the town and started buying buildings and fixing them up,” Bashaw says. He managed to buy The Virginia (rooms from $190; 25 Jackson St., Cape May; 609-884-5700;, a 24-room Victorian hotel that had become a rooming house, in 1986, shortly before attending the Wharton School for business in Philadelphia. He opened the Virginia in June 1989. Later, he took on the more daunting task of renovating the 106-room Congress Hall. The grand hotel has, since its reopening in 2002, become the social and economic center of Cape May.

As a frequent visitor to the Hamptons, Bashaw found himself drawn to Sag Harbor, in no small part because it reminded him of Cape May. He became fascinated in particular by the old Bulova Watchcase Factory, built in 1881, which had been abandoned for years. The building was designed around a large central courtyard with more than 700 oversize windows, to ensure that the workers had enough light for the delicate work of engraving and assembling watchcases. Bashaw, along with his friend and business partner Craig Wood, bought the building in 2006 and, after surviving a recession and Sag Harbor’s review process, created 64 condominiums in the center of town.

In the years that it took to get the Watchcase project off the ground, Bashaw discovered another property, Baron’s Cove (rooms from $300; 31 W. Water St., Sag Harbor; 844-227-6672;, a scruffy midcentury building on the waterfront overlooking the marina. Though never grand, the motel had been the social hub of the town in the ’60s and ’70s, before a local entrepreneur named Ted Conklin bought and renovated the American Hotel on Main Street and the action moved there. Baron’s Cove was the preferred hangout of John Steinbeck, who had lived down the road, one of many writers to have called the seaside town home, including, over the years, James Fenimore Cooper, Nelson Algren, E.L. Doctorow, Thomas Harris, Spalding Gray, Colson Whitehead, and Alan Furst. (What Cape May was to 19th-century presidents, Sag Harbor is to writers.) This May, Bashaw reopened the 67-room Baron’s Cove, which he has renovated to a luster far brighter than it was in its former low-rent heyday. We can only hope that the town retains some of its scruffy authenticity as it becomes more polished. If Sag Harbor becomes too much like the rest of the Hamptons, some of us may be tempted to move to Cape May.

Image Credit: Courtesy of The Virginia Hotel