Stepping Outside of Manhattan for a Long Island Experience

For the urbane traveler, New York City is thought to be the apogee of culture and excitement. But during late summer and early fall, everyone – even visitors – could use a respite from the sweaty, crowded, concrete jungle. And there’s no better place to visit than the city’s equally alluring neighbor, Long Island.

One of Long Island’s greatest draws is its southern shoreline. The best place to find roaring swells and superb fishing is at the end of the South Fork in Montauk. If you’re a beachgoer who prefers sun to surf, Montauk offers that, too. Check out the Montauk Point Lighthouse, which looks like a precarious beacon sitting at the end of the world. There are plenty of rooms in Montauk, but if you’re a camper, Hither Hills Campground puts you closer to the beach than any oceanfront property. While you’re there, stop for a savory bowl of New England clam chowder at the isolated restaurant Lunch in Amagansett. Also on the menu is the lobster roll, the now ubiquitous sandwich that Lunch claims to have originated. (Traveler beware: Before Labor Day, accommodations, even campsites, are hard to find, and traffic on Friday or Saturday out to the South Fork can be nightmarish.)

If you want a blend of the island’s high-priced Hamptons and relaxed Montauk (and desire a much shorter ride from Manhattan), jump into your car or ride the Long Island Railroad to the ferry stations of Bay Shore, Sayville, or Patchogue and sail over to car-free Fire Island. (Thursday to Saturday, you can hydrate at Blue Point Brewery in Patchogue, just a few blocks from the train station.) On Fire Island, plum trees and tall grass grow wild and create an idyllic vibe. The beaches are pristine and wild deer roam the dunes. If a peaceful day is your goal, head to the sleepy villages of Kismet or Saltaire, but if you’re looking to party, make Ocean Beach your destination. For a repast in OB, have a bite at Island Mermaid, next to the ferry, and enjoy views across the expansive Great South Bay. Sip down your meal with Fire Island’s indigenous libation, rocket fuel-a hopped-up piña colada.

For the more adventurous traveler, skip the ferry ride and drive to Robert Moses State Park. Find parking at field 5 and bike east, one mile past the lighthouse, onto Fire Island. Though at first the path is pocked with rocks and sand traps, once you reach the threshold of residential Kismet there are easy-to-traverse concrete and boardwalk paths. (You can also walk into Kismet and rent a bike in town.) After enjoying the quiet beaches, continue riding to the end of Atlantique, just a few miles down, and walk the mile along the beach to OB. The village of OB doesn’t allow bike riding on weekends. Further east and accessible by water taxi, or by ferry from the mainland, is a verdant sunken forest at Sailors Haven that is worth exploring.Another beach option that is less than one hour from Manhattan is Long Beach. This year, during the first two weeks of September, Long Beach will host surfing’s World Tour. The one-million-dollar prize purse (the tour’s highest ever) is attracting the world’s best surfers for the East Coast’s first ever Association of Surfing Professionals World Tour event. The town, which has a population of about 33,000 people, will be bustling. Expect skate parks, BMX riding, music venues, and crowds that are expected to reach the tens of thousands. (If you visit before Labor Day, purchase the “Beach Getaway” package for $21 from the Long Island Railroad ticketing machine; this includes round-trip fare and bargain beach access.)

Long Island also has some beautiful parks that are perfect for families, birders, and romantics. On the North Shore are Caumsett, a historic state park in Huntington, and the densely wooded Welwyn Preserve in Glen Cove. If hiking is your forte, a moderately strenuous trail begins just behind the Cold Spring Harbor library. The 26-mile adventure (though even trekking the first few miles is sufficient) makes you feel like you’re upstate.

The pearl of Long Island, however, is further along the North Shore: Wine country. Once dominated by potato fields, the North Fork has been transformed into vineyards and is ideal for winemaking thanks to its loamy soil, generous sunlight, and location between the sound and bay, which provides both natural irrigation and winds that dry the vines.

There are two roads on the northern prong that offer visitors access to the nearly 50 winemakers of Long Island: Routes 48 and 25. You’ll have a fine time traveling both, but my top five tasting rooms sit on or near to 48. If 9 a.m., midweek isn’t too early for you, Macari hosts the region’s first tasting and showcases beautiful views of its vineyard in the Mattituck Hills. Their Bergen Road is a beautiful red blend. Stop next at the island’s founding vineyard, Castello di Borghese (open at 10 a.m., a good hour before the rest). On Thursday and Sunday, tour with the owner, and an actual Italian prince, Marco Borghese. Try their pinot noir — they are one of only three vineyards in the region that attempt growing this finicky grape.

The most oddly situated tasting room is Waters Crest. Jim Waters, a retired fireman and 9/11 hero, took his garage-honed grape-stomping skills and opened his tasting room in a shopping center along Route 48. Though it’s hard to picture a quality tasting room in a strip mall, his whites and reds are unrivaled in the region. Waters also conducts Vine University, a two-day winemaking experience for those interested in learning the art. (The next one is September 10th and 11th.)

After leaving the shopping center, turn down Peconic Lane and look for a quaint yellow storefront just before the railroad crossing. This small shop is The Winemaker’s Studio, a newly opened tasting room. Winemaker Anthony Nappa breaks rules with his white pinot noir, which is typically a red wine, and his 2010 earthy Bordo, a cabernet franc that was released rebelliously early. His tastes are unique and his prices are unbeatable. The Winemaker’s Studio includes three other permanent winemakers-including John Leo, whose Family Red is superb-and Nappa also features a rotating list of noteworthy “weird” wines.

Another must-sip is Sparkling Pointe, the only winery in the state that produces purely sparkling wine. Their winemaker, born just outside of the gates of Champagne, France, has brought that acclaimed style to this Brazilian-themed, ultra-modern tasting room. Join them Friday nights for Brazilian dancing.

For breakfast or lunch, stop at Erik’s on 48. And for dinner head into Greenport or try one of the restaurants along 25. (If you find yourself on Route 25 with some extra time to drink, The Old Field Vineyards offers tastings in a rustic setting. You can also stop in at Bedell Cellars and afterward take your receipt to their sister winery up the road at Corey Creek for a free tasting.)

There’s no better time to visit the wine region than harvest season, which begins in late September. This year also happens to be an excellent time to responsibly tipple your way around the North Fork. 2007 and 2010 were the best harvests the region has ever seen, thanks to those years’ hot, dry summers. The 2007 reds are still available and the newly released 2010 whites are a prime vintage.

For accommodations, try the brand new Cedar House on Sound, which has billiards in the great room and solar panels on the roof, or Shinn Estate. Both are tranquil B&Bs run by winemakers, which means the juice keeps flowing.

If you’re traveling with kids, fear not. While you’re wining, abate the whining with stop-offs at the myriad pick-your-own apple, pumpkin, and berry patches in the area. Most of the family farms here have everything from hayrides to candy apples. Nearby, there’s shopping at the Tanger Outlet Center and fun can be had at the aquarium or at Splish Splash water park, until Labor Day.

Whether it’s beaches, parks, farms, or vineyards, there’s something for all on the island that dwarfs Manhattan.