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The Making of America’s Great Northeast Summer Resorts

We spotlight the rise of the northeast’s most affluent coastal enclaves, from yesteryear to today

This summer, the well-heeled will flock to their traditional roosts on the Atlantic Ocean, from Long Island Sound to Narragansett Bay, out to Cape Cod and the islands of Nantucket and Martha’s Vineyard. They’ll soak up the sun, the high life, and the long summer days and balmy nights cooled by sea breezes. The annual seaside escape is a summer ritual for affluent Yankees, but it wasn’t always this way.

The annual seaside escape has been a summer ritual for high society since the mid-19th century.

Credit the hustle and roar of the 19th century, with all its boom-and-bust excesses, its tycoons and captains of industry, its burgeoning middle class. And credit the whales. Especially the whales.

But first look to Rhode Island in August of 1844, three days after the illustrious New York Yacht Club had opened its doors: the founders’ eight yachts got underway from the Battery bound for Newport, Rhode Island, on the club’s maiden summer cruise.

Even before the yachtsmen arrived, Newport was a summer refuge for artists, authors (Henry and William James, Julia Ward Howe), and scientists like William Barton Rogers (founder of M.I.T.) and naturalist/engineer Alexander Agassiz. Its open, oceanfront landscape, bypassed by industrialization, beckoned to the newly minted millionaires of the Gilded Age.

Cliff Walk is the setting for many of Newport’s famous summer “cottages,” grand mansions built during the Gilded Age.

They came for the world-class sailing and the social scene and stayed for the temperate weather, a far cry from the heat and humidity of New York City. They commissioned leading architects such as William Morris Hunt to build their summer “cottages” up and down Bellevue Avenue. These were no ordinary beach houses but, rather, grand mansions with neoclassical, Italianate, Greek, and Tudor façades that enclosed palatial marble halls. No expense—or excess—was spared to build these monuments to wealth; each mansion was more elaborate and larger than the last.

The Breakers was the summer “cottage” of Cornelius Vanderbilt II. The magnificent 70-room Italian Renaissance-style mansion was designed in 1893 by Richard Morris Hunt with interiors by Jules Allard and Sons and Ogden Codman, Jr.

They all had names: The Breakers, The Elms, Rosecliff, Marble House, among them, and Beechwood, the summer home of “The Mrs. Astor” (Caroline Webster Schermerhorn Astor, to be exact), the doyenne of American society and wife of William Astor, scion to the Astor fortune. Many of her neighbors were eager for admittance into the cream of New York society, guarded by its arbiter, Mrs. Astor. That group would become known as “The 400” (370, to be exact), the number of guests who could comfortably fit into Beechwood’s glittering ballroom for Mrs. Astor’s lavish summer ball.

Sixteen miles north of Newport, Rhode Island, is the historic seaside community of Bristol Highlands. One of its finest estates is Shangri-La on Narragansett Bay. This rare property, inspired by James Hilton’s enduring 1933 novel Lost Horizon, is a stylish and carefully curated collection of four waterfront residences on 1.8 acres of private shoreline. A private sandy beach, heated infinity pool, koi pond, and uninterrupted water views are further highlights.

Newport and the historic coastal communities of Jamestown, Middletown, and Bristol remain a global center for yachting. The New York Yacht Club maintains its permanent waterfront station, Harbour Court, on Brenton’s Cove. Newport Harbor is still a highly coveted destination, both in the summer and indeed year-round. Many of the original Gilded Age mansions have been preserved by the historical society; others were purchased by 21st-century billionaires, including Beechwood, which is now owned by Oracle Corporation founder Larry Ellison.

High Society Goes “Out East”

By the end of the 19th century, it was Long Island’s turn to receive high society. More than a thousand mansions were built on Long Island’s North Shore from the late 1800s to the 1930s. Aptly dubbed the Gold Coast, this gilded enclave was the summer playground for New York’s nouveau riche and old money set. The wide stretches of open farmland and protected beaches served well for their grand villas, castles and and châteaux, many of which were imported from the Old World, lock, stock, and barrel, and reconstructed “out east.”

Oheka Castle in the North Shore hamlet of West Hills was the home of financier and philanthropist Otto Kahn. Built from 1914 to 1919, the 127-room, 109,000-square-foot residence on 443 acres included an 18-hole golf course, tennis courts, a landing strip, and stables. It was the second largest home ever built in the United States and is today a luxury hotel.

F. Scott Fitzgerald’s The Great Gatsby immortalized the arriviste glitz and glamor of the North Shore summers during the Roaring Twenties. Cow Neck and Great Neck, on Manhasset Bay, were the West and East Egg of the novel, where “white palaces glittered along the water.” Jay Gatsby’s estate was merely 40 acres, while the neighboring properties of the “staid nobility of the countryside” were 10 times its size, limestone castles and palaces set like jewels in baroque gardens, with stables and paddocks, mazes, croquet lawns, tennis courts, and swimming pools. Their real-life owners were America’s wealthiest families―Astor, Vanderbilt, Phipps, du Pont, Woolworth, Guggenheim―the fortunate few, whose seasons in the sun really were as ostentatious as their fictional counterparts.

Seventy miles east, the South Fork of Long Island is a place the New York Times dubbed “Eden.” In an article from 1893, the small coastal villages of the Hamptons were described as “Exclusive—in the best sense of the word—society is here represented during the summer by its choicest spirits.”

The windswept Atlantic Ocean beaches of the Hamptons have been a draw for the elite for well over a century.

The Hamptons comprise the seaboard towns of Southampton and East Hampton, within which are smaller hamlets, such as Bridgehampton, Westhampton, Sag Harbor, and Montauk. Back then, the journey to the Hamptons was a long, rickety train ride from New York City to Bridgehampton. An extension of the track all the way to Montauk put the Hamptons firmly on the tourist map. First came the modest summer colonies, then the golf courses and tennis clubs, and by 1910, the Hamptons had become a haven for the wealthy. The artists arrived in the ’40s and ’50s, Jackson Pollock followed by Willem de Kooning and Andy Warhol; the writers Kurt Vonnegut, Joseph Heller, Philip Roth, and then a throng of musicians and Hollywood actors.

Further development from the 1960s to the ‘80s completed the Hamptons’ transformation from an agrarian backwater into one of the world’s most coveted summer resort destinations.

Montauk Beachfront Paradise is a masterpiece of oceanfront living in exclusive Montauk Point at the tip of the Hamptons. The 7,000-square-foot tea house-inspired main residence sits atop a bluff overlooking its own 36-acre nature preserve with ponds and walking trails that lead to a secluded sandy beach with access to world-class surfing and ocean fishing.

The Hamptons are still the place to be every weekend from Memorial Day to Labor Day each year. The well-heeled and the well-known (and the almost-known who watch them) come for the powdery sand beaches along the Atlantic Ocean and Peconic Bay; the world-class recreation, golf, showjumping, and sailing; and, the Hamptons unrivaled social scene: haute restaurants and nightlife, art shows, charity fundraisers, and parties, lots of parties. The pilgrimage from New York City to this storied summer resort is two to three hours by car (if you leave by dawn or dusk) or train, or—the preferred way to travel—half an hour by seaplane or helicopter.

You’re Sure to Fall in Love with Old Cape Cod . . .

For Bostonian trippers, the summer destination of choice has always been the Cape. Today, the very well-heeled sail or fly across Nantucket Sound to the islands of Nantucket and Martha’s Vineyard. These are the quintessential New England summer resorts: quaint fishing villages, colonial towns, candy-colored lighthouses, lobster shacks, ice cream parlors, wide, sandy beaches, and tranquil “kettle” ponds ideal for bathing.

Medouie Creek Estate is a grand coastal compound on Nantucket. Built by Bob Wright, the former long-time CEO of NBC, the property includes an elegant main residence, guest house, poolhouse, and two-bay carriage house, complemented by an array of recreational amenities and panoramic views of Polpis Harbor.

Like much of the Northeast coast, its history is tied to shipping and whaling, the fortune-building industries of the 17th and early 18th centuries. In the 19th century, the Cape’s first tourists came from Boston by stagecoach and boat. In 1848, a train took beachgoers from Boston to Sandwich, and by 1873 to the tip of the Cape, or the “end of the world” as locals called it, Provincetown, “P-town,” where the Mayflower first landed in 1620. In 1914, the Cape Cod Canal was built, connecting Cape Cod Bay to Nantucket Sound, followed by the Cape Cod Canal Bridge.

This world-class offering is located in in the exclusive Homers Pond Association on the south shore of Martha's Vineyard. The property comprises more than 280 acres, of which 141 acres are conservation restricted, and includes more than half a mile of beachfront. The remaining acreage is currently subdivided into five lots, one of which has a four-bedroom residence with pool and tennis court, and another lot with a beach house, and is complete with infrastructure and utilities.

It was America’s most famous family that put Cape Cod on the map. In 1926, its patriarch Joseph P. Kennedy rented a summer cottage in Hyannis Port. He later purchased a clapboard waterfront cottage for his wife, Rose, and their growing family to spend their summers. The three-home compound on six acres would serve as the headquarters of then Sen. John F. Kennedy’s presidential campaign and later as his summer White House.

Former First Lady of the United States Jacqueline Kennedy Onassis was drawn to the dunes, ponds, and rolling hills of Aquinnah on Martha’s Vineyard. She purchased Red Gate Farm in 1979 as a summer home and refuge from the world stage, and as a legacy for her children and grandchildren. The serene and private 340-acre sanctuary with over a mile of Atlantic Ocean beachfront and two freshwater ponds has been treasured and preserved for 40 years.

About Those Whales . . .

Many wealthy Bostonians ventured farther afield, across Nantucket Sound, to reach the island escapes of Nantucket and Martha’s Vineyard. Centers of the whaling industry from the early 1700s to the mid-1800s, they were famously portrayed in Herman Melville’s classic novel Moby Dick. The rise of the oil industry and the collapse of whaling devastated the islands’ economies.

The quintessential New England summer resort of Martha’s Vineyard is characterized by grand colonial mansions, quaint beachfront cottages, historic lighthouses, pristine sandy beaches and kettle ponds.

Tourism beckoned. Nantucket remained isolated until the Old Colony railroad reached mainland Woods Hole in 1872, and summer residences began to appear. Largely undeveloped until the mid-20th century, Nantucket offered developers large tracts of oceanfront land. The first major tourists on Martha’s Vineyard were thousands of Methodist revivalists, who pitched their summer tent campsites—and later built cottages—in the groves and pastures of Oak Bluffs. Both these picture-postcard islands had miles of coastline with dozens of beaches, either protected by the sound or vast stretches along the Atlantic Ocean with views at sunrise or sunset.

And the whales came back. Today, Nantucket excursionists can spot humpbacks and finbacks galore, sometimes minke whales, right whales, pilot whales and, rarely, sperm whales, beluga whales, sei whales, and blues.

Once hunted to the edge of extinction, humpback, minke, pilot, and other species of whale pass through Nantucket Sound on their migratory routes. The Sound also sustains a wide variety of marine life, including porpoises, turtles, and a thriving colony of gray seals.

The Hidden Treasures of the Sound

Connecticut has a necklace of beaches on Long Island Sound in the 24 towns along its shore from New York to Rhode Island. There are prestigious commuter havens on the ocean like Greenwich (an hour and a quarter by rail from Manhattan) and Old Lyme (two hours). Old Saybrook (three hours)—just a ferry ride across the Sound from the North Fork of Long Island—has a performing arts center called “the Kate,” in honor of longtime resident Katherine Hepburn.

One of Long Island Sound's celebrated Thimble Islands, Potato Island commands a spectacular setting just off the coast of Connecticut. At the southern end of this one-acre private retreat is a beautifully restored circa-1912 main residence. A swimming pool, granite hot tub nestled into the rocks, manicured gardens. and a private deepwater dock are among the outstanding amenities.

Gilded Age millionaires who wanted a taste of the island lifestyle bought their own private isles. Off the coast of Branford, Connecticut, are the Thimbles, a chain of 365 tiny islands (just 23 are habitable) in Long Island Sound, 90 miles from Manhattan. Dutch explorer Adriaen Block discovered the Thimble Islands during an exploration of Long Island Sound. In the late 1600s, it is alleged that the pirate Captain William Kidd buried treasure there. By the mid-1800s, word had reached New York City and New Haven, and the Thimbles tourism industry was born. Local legend asserts that for two summers President William Howard Taft had a home on the islands. Another legendary resident was showman Gen. Tom Thumb of P.T. Barnum fame.

The Call of “The Shore”

The development of the 125 miles of New Jersey shoreline as a recreational resource began nearly two centuries ago. Cape May was the first resort. Atlantic City was the latecomer. Envisioned in the mid-19th century as a giant health spa to rival Coney Island’s popularity, it proved too popular with the masses to lure the elites of New York and Philadelphia. The most desirable stretch of the “The Shore” are the tony northern enclaves, Middletown, Rusden, and Spring Lake.

Named for the spring-fed lake at its center, Spring Lake was incorporated in 1903. But the lovely seashore town was already a popular summer sojourn for affluent residents of Manhattan and Philadelphia. Grand Italianate hotels, such as the Ocean House and The Breakers, ice cream parlors, emporiums, and the sweeping white-sand beach had been a draw since the 1870s. The Spring Lake Bath and Tennis Club was established in 1898, cementing Spring Lake’s reputation as the “Jewel of the Jersey Shore.”

The elegant north shore community of Middletown is aptly named for its scenic setting between the Navesink River and Sandy Hook Bay. The sleepy fishing village evolved into a summer enclave in the post-Civil War years, its first summer visitors arriving in steamboats from New York Harbor. Well-to-do New Yorkers gravitated to the area in the late 1800s and built their Beaux Arts-style manor houses along the banks of the Navesink River. The 1939 construction of the Oceanic Bridge, which connected Middletown and the Rumson-Red Bank peninsula, added to the area’s prosperity.

High Point Estate in Middletown, New Jersey, is an elegant French-inspired residence designed by renowned architect Robert A. M. Stern with interior finishes by master craftsman Pierre Finkelstein. The property is further enhanced by four outbuildings, a heated pool and two cabanas, a boat dock, and magnificent gardens based on an original design by the Olmsted Brothers.

A mile west of the Jersey Shore is the coveted riverfront enclave of Rumson. The community appealed to those looking for a riverfront escape between the Navesink and Shrewsbury Rivers. The Sea Bright Lawn Tennis and Cricket Club, founded in 1877, and the Rumson Country Club, established circa 1908, added to the resort appeal.

By the 1850s, a number of “cottages,” hotels, and inns were constructed along the Manasquan River at or near Union Landing in Brielle. In May 1888, Robert Louis Stevenson arrived to spend a month polishing his novel The Master of Ballantrae. Fred Astaire was also a regular visitor. The Brielle Land Association was formed in 1881, 150 acres of farmland between Longstreet’s Creek for subdivision into vacation homesites. It was named after Brielle, Holland, for its resemblance to the Dutch lowlands. The 140-acre Manasquan River Golf Club was founded in 1922, and, in the post-World War II years, Brielle became an affluent residential suburb.

These beautiful shore communities are still a magnet for the wealthy. The allure is evident: proximity to Manhattan (just 45 minutes by high-speed ferry) and elegant Victorian and Edwardian estates on the Manasquan River, Debbie’s Creek, and the Glimmer Glass tidal inlet.

This unique waterfront home in Brielle combines the owner’s architectural vision with the sweeping beauty of the Manasquan River as its backdrop. Sui Generis is a stunning 31,000-square-foot residence featuring nine bedrooms, a wine cellar, billiards room, theater, a pool with cabana, bar, and outdoor kitchen, Japanese-style garden, and two deepwater docks to accommodate boats of up to 65 feet.

Like Newport, the Jersey Shore’s development of upmarket resorts began with the northern states’ post-Civil War boom: Rapid industrialization, a growing workforce, and breakneck economic expansion left the North awash in liquidity—and speculation. Unlike Newport, the Cape and its islands, “The Shore” suffered harshly in the 19th-century’s boom-and-bust expansion, its fortunes punctuated by great hotel fires and hurricane devastation. Not until the mid-20th century’s preservationist movement, with landmarking and historic district status, were the crown jewel resorts of the Jersey Shore truly saved.

And, yes, all up and down the Northeast coastline, the whales are back, too.