Exploring the Hamptons East of the Shinnecock Canal

Southampton Village

Southampton Village is the posh Hampton. Home to multi-million dollar homes and beachfront estates hidden behind 20 foot hedgerows, there is no doubt why glitterati of the Hamptons gather here. Shop the boutiques and art galleries on Main Street and Job's Lane, and have a rest at one of the many cafes and restaurants that line the business district. Be aware that proper attire is required. Street clothes please, as beach wear will get you a ticket. Besides, you will want to be well dressed when you rub shoulders with a favorite celebrity and stop for a selfie.

Points of Interest in Southampton Village

  • Shinnecock Indian Reservation (Look for Labor Day Weekend Pow Wow)
  • Lake Agawam
  • Conscience Point Par
  • Southampton Historical Museum Buildings


Water Mill is small but easy to notice as eastbound traffic typically slows along the business district, but what a view! The scenic mill pond is to the north, and Mecox Bay to the south offers expansive sights on a clear day. Be sure to notice the Beebe Windmill in the village green. Just a cruise through town offers sights of the rich history of the Hamptons. Coffee shops, a gourmet food emporium and boutiques are also along this stretch of the Montauk Highway. Find farm fresh produce at the Milk Pail Farmstand, located on the east side of the hamlet.

Points of Interest in in Watermill

  • Flying Point Beach
  • Parrish Art Museum
  • Duck Walk Vineyards


Bridgehampton has a bit of everything. Antique shops, art galleries, great restaurants and it boasts the largest shopping center east of the canal. Look for activities and events at the Bridgehampton Community House, and the Bridge Hampton Historical Museum. Don't forget to stop at Candy Kitchen for a sweet treat, too.

Points of Interest in in Bridgehampton

  • Hampton Classic (Late August)
  • Children's Museum of the East End
  • South Fork Natural History Museum and Nature Center
  • Channing Daughters Winery

Sag Harbor

Sag Harbor is found on the north shore of the South Fork brimming with nautical Hamptons charm. Park on Long Wharf to view the yachts berthed for the summer and stroll the village for any amenity you seek. Fine dining, local pubs, art galleries, antique shops and charming boutiques are all an easy walk from a parked car.

Points of Interest in in Sag Harbor

  • Long Wharf
  • Mashashimuet Park
  • Long Beach
  • Morton Wildlife Refuge (Noyac)
  • Trout Pond


Sagaponack is on the road to East Hampton, and seems like a land that time forgot. Travel down Sagg Main Street to find the general store and post office along with one of the last one-room school houses still in operation on Long Island. The farmviews are magnificent, as is the sugar sand Sagg Main Beach. While most of the wineries are found on the North Fork, Sagaponack is home to the only farmstand to feature wine at the Wolffer Wine Stand, with varietals produce from grapes grown at Wolffer Estate, also in Sagaponack.

Points of Interest in in Sagaponack

  • Sang Main Beach
  • Wolffer Estate Winery
  • Wolffer Wine Stand
  • Poxabogue Golf Course (Open to the public)

East Hampton

East Hampton is the refined sister of Southampton. Elegant and posh with a more reserved demeanor than the opulent Southampton. History buffs will love the 17th Century Saltbox houses that are open for tours, and the majestic Hook Mill. Like Bridgehampton, there are boutiques, antique shops, and cafes to suit any preference and budget. East Hampton is also home to Main Beach, which frequently appears on best beaches of the world lists.

Points of Interest in in East Hampton

  • Main Beach
  • Town Pond
  • Home Sweet Home (where the song was written)
  • Mulford Farm
  • Hook Mill
  • Herricks Park (Home field for the Artists and Writers Charity Baseball Game)
  • East Hampton Village Nature Trail
  • Buckskill Tennis Club


Amagansett will be the last stop before you embark on the 5 mile journey to Montauk across the Napeague Stretch. Yet another Hamptons charmer, the Main Street district boasts restaurants, inns, boutiques and art galleries with the special addition of Stephen Talkhouse, a bar/nightclub that attracts national music acts, and even boasted an impromptu performance from Sir Paul McCartney himself one Christmas season. For fresh local produce stop at Amagansett Farmer's Market, the best and most famous farmer's market in Hamptons.

Points of Interest in in Amagansett

  • East Hampton Town Marine Museum
  • Amagansett Farmer's Market
  • Stephen Talkhouse