Best of

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.

12 winners and 24 runners-up across 9 towns, west to east. Filled dots are the winners.

SouthamptonWater MillBridgehamptonSagaponackEast HamptonAmagansettMontaukSag HarborShelter Island

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…
Runner-up
Main Beach (East Hampton)
Runner-up
Ditch Plains (Montauk)
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.
Runner-up
The Lobster Roll ("LUNCH") (Amagansett)
Runner-up
Bostwick's Chowder House (East Hampton)
03 · THE BREAKFAST
Carissa's the Bakery
East Hampton · Winner, 2026
The bread alone justifies the line out the door.
Runner-up
Hampton Chutney Co. (East Hampton)
Runner-up
The Golden Pear (East Hampton)
04 · THE SCOOP
John's Drive-In
Montauk · Winner, 2026
A 1960s roadside box on the way out to the Point.
Runner-up
Bridgehampton Candy Kitchen (Bridgehampton)
Runner-up
Sip 'n Soda (Southampton)
05 · THE VINEYARD
Wölffer Estate Vineyard
Sagaponack · Winner, 2026
Summer in a Pink glass.
Runner-up
Channing Daughters Winery (Bridgehampton)
Runner-up
The Wine Stand at Wölffer (Sagaponack)
06 · THE SUNSET
Sunset Beach
Shelter Island · Winner, 2026
The name is not a coincidence.
Runner-up
Navy Beach (Montauk)
Runner-up
Gosman's Dock (Montauk)
07 · THE SUNRISE
Montauk Point Lighthouse
Montauk · Winner, 2026
First light in New York State, full stop.
Runner-up
Ditch Plains Beach (Montauk)
Runner-up
Indian Wells Beach (Amagansett)
08 · THE NIGHT OUT
Stephen Talkhouse
Amagansett · Winner, 2026
A shingled bar where arena acts play to a room of 100.
Runner-up
The Surf Lodge (Montauk)
Runner-up
75 Main (Southampton)
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)
Runner-up
Stony Hill Stables (Amagansett)
10 · THE SPA DAY
Shou Sugi Ban House
Water Mill · Winner, 2026
Japanese bathing ritual meets Hamptons barn minimalism.
Runner-up
Gurney's Seawater Spa (Montauk)
Runner-up
Naturopathica (East Hampton)
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)
Runner-up
Hither Woods (Montauk)
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.
Runner-up
Bridgehampton Candy Kitchen (Bridgehampton)
Runner-up
Sip 'n Soda (Southampton)

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.