THE 2026 AWARDS

Best of the East End

Twelve categories, one winner each, no ties. These are the editorial picks — argued over, revisited each season, and chosen from the places already covered across this guide. Every pick links back to its full write-up.

01 · THE BEACH
Coopers Beach
Southampton · Winner, 2026
Wide white sand, full services, and a regular on the national top-ten lists — the rare beach that earns its day-parking fee.
Runner-up
Main Beach (East Hampton) — The classic village beach — pavilion, flags, and the long view down the dunes.
Runner-up
Ditch Plains (Montauk) — The surf beach. Longboards at dawn, the trailer crowd at noon.
02 · THE LOBSTER ROLL
Duryea's Lobster Deck
Montauk · Winner, 2026
On the water at Fort Pond Bay, the roll that launched a thousand boat photos. Go at golden hour and accept the wait.
Runner-up
The Lobster Roll ("LUNCH") (Amagansett) — The Napeague stretch original with the famous roadside sign, slinging rolls since 1965.
Runner-up
Bostwick's Chowder House (East Hampton) — The locals' answer — no scene, just chowder and a properly dressed roll.
03 · THE BREAKFAST
Carissa's the Bakery
East Hampton · Winner, 2026
The bread alone justifies the line out the door. Pastry case to plan a morning around.
Runner-up
Hampton Chutney Co. (East Hampton) — Dosas in Amagansett Square's old church — the un-bagel breakfast.
Runner-up
The Golden Pear (East Hampton) — The dependable village counter, four hamlets strong.
04 · THE SCOOP
John's Drive-In
Montauk · Winner, 2026
A 1960s roadside box on the way out to the Point. The dipped cone is the move.
Runner-up
Bridgehampton Candy Kitchen (Bridgehampton) — Booths, counter stools, and sundaes unchanged since 1925.
Runner-up
Sip 'n Soda (Southampton) — Homemade ice cream and a working soda fountain — the genuine article.
05 · THE VINEYARD
Wölffer Estate Vineyard
Sagaponack · Winner, 2026
Summer in a Pink glass. The Saturday sunset at the Wine Stand is its own social season.
Runner-up
Channing Daughters Winery (Bridgehampton) — The winemaker's winery — odd varietals, sculpture in the vines, no crowds.
Runner-up
The Wine Stand at Wölffer (Sagaponack) — Live music, vineyard rows, and the last light over the vines.
06 · THE SUNSET
Sunset Beach
Shelter Island · Winner, 2026
The name is not a coincidence. West over Shelter Island Sound, rosé optional but customary.
Runner-up
Navy Beach (Montauk) — Fort Pond Bay's broadest western horizon, toes in the sand.
Runner-up
Gosman's Dock (Montauk) — Working harbor, returning boats, and the inlet glowing orange.
07 · THE SUNRISE
Montauk Point Lighthouse
Montauk · Winner, 2026
First light in New York State, full stop. Arrive for blue hour and watch the Atlantic switch on.
Runner-up
Ditch Plains Beach (Montauk) — Dawn patrol with the surfers — the East End's best alarm clock.
Runner-up
Indian Wells Beach (Amagansett) — Empty sand and a clean eastern horizon, ten minutes from the village.
08 · THE NIGHT OUT
Stephen Talkhouse
Amagansett · Winner, 2026
A shingled bar where arena acts play to a room of 100. Fifty years of the East End's best nights.
Runner-up
The Surf Lodge (Montauk) — The deck at sunset is the summer's most photographed stage.
Runner-up
75 Main (Southampton) — Where Southampton's dinner crowd forgets to go home.
09 · THE RIDE
Deep Hollow Ranch
Montauk · Winner, 2026
The oldest working cattle ranch in America, and the seasonal beach ride is the East End's single best photo op.
Runner-up
Wölffer Estate Stables (Sagaponack) — Manicured rings beside the vines — the show-jumping end of the spectrum.
Runner-up
Stony Hill Stables (Amagansett) — The teaching barn generations of East End riders started at.
10 · THE SPA DAY
Shou Sugi Ban House
Water Mill · Winner, 2026
Japanese bathing ritual meets Hamptons barn minimalism. The full-day pass resets a whole season.
Runner-up
Gurney's Seawater Spa (Montauk) — The only ocean-fed seawater pool in North America, with the Atlantic out the window.
Runner-up
Naturopathica (East Hampton) — The serious-facial institution, East Hampton edition.
11 · THE HIKE
Paumanok Path
Montauk · Winner, 2026
The through-trail of the South Fork — pick the final Montauk moorland stretch for ocean-bluff drama.
Runner-up
Shadmoor State Park (Montauk) — Hoodoo bluffs and a beach you scramble down to.
Runner-up
Hither Woods (Montauk) — The deep-woods network — hike it or ride it.
12 · THE INSTITUTION
The American Hotel
Sag Harbor · Winner, 2026
Since 1846: the bar, the wine list, the wood-paneled time machine on Main Street. The East End's living room.
Runner-up
Bridgehampton Candy Kitchen (Bridgehampton) — The luncheonette that anchors the Main Street, century one complete.
Runner-up
Sip 'n Soda (Southampton) — Family-run since 1958, soda jerks and all.

How these are chosen: editorial picks only, revisited each season. No venue pays to appear, no awards are sold, and inclusion follows the same independence rules as the rest of this guide. Disagree? Make your case.