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Is there anything finer after a long week of work than a weekend in the country? Well for New Yorkers, the country often means the Hamptons – a roughly 200-square-mile collection of former fishing and whaling villages that dot the South Fork of Long Island’s lush farmlands and white sand beaches, about 90 miles east of Manhattan. 

Long known as a summer getaway for society types, celebrities such as Steven Spielberg and Sean “P Diddy” Combs now flock to the area, which includes Southampton in the west, Sag Harbor to the north and  Water Mill, Bridgehampton, Amagansett, East Hampton and Montauk in the east.

During the Hamptons’ high season -- between Memorial Day (the last Monday of May) and Labor Day (the first Monday of September) -- the crowds and the prices are at their peak. But on the Tuesday after Labor Day, affectionately known by locals as “Tumbleweed Tuesday”, the crowds almost uniformly disappear, and this playground of the wealthy opens to everyone.  

“The offseason is when I come out of hiding,” said Bridgehampton resident Walker Vreeland. “It is the time of year that casts the Hamptons in the most picturesque light. It goes from being 'the Hollywood of the East Coast', to a collection of quaint, historic small towns, each with its own distinct charm.”

Exploring the region
The primary draw of the Hamptons is its spectacular beaches backed by fabulous homes, picket-fenced wild dunes and clustering gulls. While the summer is the obvious time to head to the beach, there is something sublime about the crisp sea air on a spring or autumn day when the sands are empty save for the occasional dog walker and jogger. Two of the better choices (for ease of access and overall popularity with the locals) are Flying Point Beach in Southampton and Main Beach in East Hampton. Both are public beaches, and with a small parking fee (often avoidable in the off-season) you can walk across the sandy expanse for miles in either direction, taking a near-private tour of areas crowded with people during the high season.

As the Hamptons cover a large land area, it is best to have a car if you plan on travelling between several sites, although town centres are accessible from their respective Long Island Railroad stations and taxis are widely available. One of the best parts of visiting in the off-season is that its traffic-clogged main roadway (Route 27) is much more navigable and trips between towns take a fraction of the time.

With its flat terrain and long vistas, exploring the Hamptons by bicycle can be an good way to peek behind the gates and in-between the hedgerows of the mega-mansions on Lily Pond Lane in East Hampton or Ocean Road in Bridgehampton, or to explore the long boulevards interspersed with charming shops and restaurants. If you did not bring your own bike, you can rent one at a number of places in Sag Harbor, Southampton and East Hampton. The weather, like most of the East Coast, fluctuates wildly in the fall and spring, so cycling is sometimes possible well into November and as early as April.

For particularly blustery or cold days, ditch the bike, grab your swimsuit and head to Montauk to enjoy the luxurious indoor sea water pool at Gurney’s Inn. With the poolhouse’s large picture windows and chaise lounges overlooking the crashing waves on the windswept beach, you will feel like you are enjoying a spectacular day at the beach while floating in their heated pool. Double down on the glamour and book a facial and massage in the full-service spa. .

After a long day of beach walking, swimming or biking, stop by the Wolffer Estate Vineyard in Bridgehampton to sample their wares. Their tasting room, with large windows and French doors looking out over the vines, is a superb place to relax. A fun event for kids and adults alike is the annual harvest fair on the first weekend in October with the traditional hay-rides, pumpkin carving and, of course, wine-tasting.

In the evening, stop by the Stephen Talkhouse pub in Amagansett, which has been serving up live music and brews since 1970; past acts range from local bands to the bard of Long Island himself, Billy Joel. It is standing room only in summer, but as the weather gets brisker it becomes easier to grab a seat and enjoy the ambiance.

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