Ranching may seem a tad Wild West for the East End, but Montauk was once the terminus for huge cattle drives from the rest of Long Island. The still-roping Deep Hollow Ranch, three miles east of the village, is the oldest working cattle ranch in the country, and the only place on the East End that offers both Western- and English-style riding lessons. A half-hour trail ride ($35) alongside grazing Texas longhorns is a perfect activity for kids (age six and below). And the 90-minute, four-mile beach ride ($75) is a decidedly un-glitzy alternative to watching polo in Bridgehampton.
After working up a cowboy-size appetite, head back to Montauk Harbor to feast on a bowl of mussels in coconut milk or monkfish with three chutneys and roasted summer vegetables at the year-old Inlet Seafood Restaurant, a sustainable-minded spot owned by a group of local boat captains.