This town of about 4,000 people sits like a shingled island among the protected forest, rolling grasslands, and foamy breakers tumbling in from the Atlantic. It’s a refreshing cocoon of preserved land. (Sixty-five percent of the town is protected in a preservation fund.) The community is driven by entrepreneurs, savvy business people, and conservationists—all dedicated to preserving Montauk.
2 of 6Photographer Tara Donne
Your View Is:
Blue. The expansive Atlantic Ocean opens up unimpeded from the town’s front door.
3 of 6Photographer Tara Donne
Your Main Street Has:
Shagwong’s Tavern for fish-and-chips or lobster, the Gig Shack for breakfast in the sun and live music at night, Montauk Bookshop, and Stu Foley’s Air and Speed Surf Shop.
4 of 6Photographer Tara Donne
Your Best Beach Is:
Ditch Plains for surfing, and Gin Beach for families and swimming.
On the Weekend you Might: play golf at the Montauk Downs public course designed by Robert Trent Jones, Sr., hike in Hither Hills State Park, or attend the Montauk Chamber of Commerce’s Night at the Light wine and food event.
5 of 6Photographer Tara Donne
Your Neighbors Like To:
Surf, play tennis, discuss land conservation and historic preservation, hike at Montauk Point State Park, sneak into East Hampton for a drink.
6 of 6Photographer Tara Donne
Stay a week: The Solé East Resort is a hip surfer boutique. Rates start at $99; 631/668-2105 or soleeast.com.
Stay a month: Oceanview beach cottage, three bedrooms, two and a half baths. Weekly rates start at $2,000; 631/968-0333 or vrbo.com/129952.