Long Island East End: Montauk Lighthouse, Hither Hills & Shelter Island

A 1,755-acre state park in the Napeague Harbor area between East Hampton and Montauk, with a unique 'walking dunes' formation — parabolic dunes 80 feet high that migrate inland at 3 feet per year, burying and then revealing a pitch pine forest. The ghost forest of dead pine trunks emerging from the dune face is one of the strangest natural landscapes in New York. The 3-mile loop trail crosses active dune and the submerged forest.

The oldest lighthouse in New York, built in 1796 by order of George Washington — the 110-foot tower stands on the bluff above the sea cliffs at the extreme east end of Long Island, with views of the open Atlantic, Block Island Sound, and Rhode Island on clear days. The lighthouse is still an active Coast Guard aid to navigation; the museum in the keeper's cottage traces 200 years of Montauk maritime history.

The public golf course at Montauk Downs is considered the finest public course in New York — a 1968 Robert Trent Jones design on a dramatic oceanside site. The adjacent Montauk Downs trail system traverses the park's maritime scrub oak and blueberry heathland, with views to the south of the Atlantic surf and north to Fort Pond Bay.

A Montauk Harbor restaurant since 1988, serving the sportfishing fleet's catch through a menu that changes daily based on what's landed at the adjacent dock. The whole grilled striped bass, the yellowfin tuna, and the Montauk lobster are the summer anchors; the outdoor deck faces the working harbor.

A 185-acre Nature Conservancy preserve on the Amagansett oceanfront, protecting the primary and secondary dune systems with a 2-mile trail through beach grass, bayberry, and maritime oak. The secondary dune in this section is 30 feet high — unusually large for the South Shore — and the interdunal swale between the primary and secondary dune is a freshwater wetland supporting rare coastal plain plant communities.

The 1879 farmhouse in Springs where Jackson Pollock and Lee Krasner lived from 1945 until Pollock's death in 1956, with the cedar-floored barn studio where Pollock developed his drip-painting technique from 1945 to 1950 still intact — the floor's paint drips are preserved as a work of art in themselves. Springs was the center of the New York School of abstract expressionism's summer retreat; de Kooning, Motherwell, and Elaine de Kooning all worked nearby.

The Shelter Island North Ferry from Greenport takes 7 minutes across Shelter Island Sound — a flat-bottomed cable ferry that has crossed this passage since 1908. Shelter Island is a middle island between the North and South Forks of Long Island, accessible only by ferry from either fork, with 2,000 acres of Nature Conservancy preserve covering one-third of the island.

A 2,039-acre Nature Conservancy preserve covering the southern third of Shelter Island — one of the finest examples of undisturbed coastal temperate forest on the Mid-Atlantic coast. Four loop trails (2 to 11 miles) traverse salt marshes, tidal creeks, old-growth beech stands, and osprey nesting areas. The 11-mile Blue Trail is the most complete cross-section; the 2-mile Red Trail is the choice for the afternoon.

A 1,520-acre preserve on Lloyd Neck (Cold Spring Harbor township) that was the hunting estate of Marshall Field III (1921-1956), with 8 miles of trail through hardwood forest to a Long Island Sound beach at the end of a 2-mile walk. The preserve has the largest undeveloped saltmarsh on Long Island's north shore, a dairy barn complex (1922, completed but never operated), and a view north to Connecticut's hills from the beach.

A secondary trail network in the Cold Spring Harbor watershed, with the freshwater outlet creek accessible by a 1.5-mile trail through oak woodland to a fish hatchery (one of the oldest in New York, operating since 1868) where Atlantic salmon smolts are raised for Long Island Sound stocking.

A 3.5-mile section of the Long Island Greenbelt trail from Sunken Meadow's western trailhead through Caleb Smith State Park Preserve, with old-growth oak and beech forest and a tidal river crossing. The Long Island Sound beach at Sunken Meadow is the widest natural beach on the north shore.

A Huntington village staple for upscale seafood and steaks, Prime sits steps from the harbor on Main Street and serves local fluke, Long Island duck, and dry-aged beef alongside an excellent wine list. The ideal north shore send-off dinner before the 45-minute drive back to New York City.