Need a break from the big city? View 42-hour itineraries from 13 cities.More
Established in 1658, Deep Hollow Ranch claims to be the oldest working cattle ranch in the country. The sunset beach rides are unforgettable, as are the trail rides through Theodore Roosevelt County Park, across the road. Pony rides keep little ones occupied. English and Western riding lessons, outdoor barbecue dinners and bonfires, wagon tours, and historical reenactments are among the special things to do and see here. Montauk Hwy. across from Theodore Roosevelt County Park, Montauk, NY, 11954. 631/668–2744. www.deephollowranch.com.