Bridgehampton

 

Best-known for its world-class riding events, such as the Hamptons Classic and the Bridgehampton Polo Club matches, this 13.5-square-mile hamlet is an ideal second home to the equine elite. Solidly upscale but still accessible, Bridgehampton is the place to go for those who have it but don’t necessarily feel the need to flaunt it.

 

Bisected roughly in half by Montauk Highway, classic farmhouses and stables dot the pastoral northern landscape of the East End’s most rural nabe, while modern manses populate the southern, ocean-proximate areas. A winsome Main Street straddles the two, with retail and dining selections that strike a fine balance between country ease and haute cuisine. Big box-type shopping is also close by, thanks to the Bridgehampton Commons shopping center.

Low-key but still lively, Bridgehamptoners appreciate the simple luxuries in life—fine food and quality goods without pretense. North of Montauk Highway is nirvana for the horse-and-stable set, as well as for those who are looking for a property that’s a cut above, but still accessible.

The hamlet makes the most of its limited oceanfront; Scott Cameron, Ocean Road, and Mecox Beach are fan favorites with residents and day-trippers alike. Bridgehampton is off the guidebook radar, so the seasonal crowds often bypass it entirely. As a result, the locals get to keep their shops, restaurants, and favorite beach spots to themselves.

 

The secondary waterfronts at Mecox Bay, Kellis Pond, Sagaponack Pond, and Long Pond augment the community’s other natural wonders, including the Long Pond Greenbelt, the South Fork Natural History Museum, Bridge Gardens, and the giant corn maze at Fairview Farm. For kids, there’s a highly regarded Children’s Museum of the East End and one of the best-funded schools in the country. For adults, there’s top-notch fine dining and shopping, plus Channing Daughters Winery.