Though Southampton and East Hampton get all the attention, Montauk’s natural beauty is unrivaled on the East End. Over 500 feet of beautiful, clean, and uncrowded sand can be found at Kirk Park Beach, just west of the village, beside the IGA market. Public parking—a rarity in these parts—costs $15 per day.
A half-mile east of Montauk, Shadmoor State Park features unique, moorlike terrain and elevated platforms offering spectacular vistas. Hike the 1¼-mile loop trail through the scrubland, gawking at panoramic ocean views from the tops of 70- to 100-foot bluffs.
For some of the best mountain biking on Long Island, rent wheels from Montauk Bike Shop (from $9 an hour or $35 a day) and make the classic, hilly pilgrimage to the Montauk Lighthouse. Or pick up a $7 Ride Guide and explore the many trails and vistas in sprawling Hither Woods, west of the village.
The jetty at Ditch Plains Beach creates consistently rideable waves, suitable for both long- and short-boarders and beginners. When it gets too crowded, seasoned surfers should check out the breaks at Turtle Cove (located below the Montauk lighthouse) or Camp Hero State Park. Rent boards or sign up for lessons at Air and Speed Board Shop (795 Montauk Highway; 631-668-0356).
After toweling off, join the regulars at the traditional countdown-to-sunset cocktail hour at the Montauket (88 Firestone Road; 631-668-5992). Grab a picnic table and a piña colada and cheer along with the crowd as the sun dissolves into glimmering Fort Pond Bay.