These days, East End towns are just as welcoming in the fall as during the summer season. After the crowds subside, spend a day in Montauk or Greenport, discovering what is appealing now while enjoying their timeless seaside charm.
Dramatic ocean views, the freshest seafood and surf culture beckon day-trippers to Montauk well beyond Labor Day. Arrive bright and early and treat yourself to a jelly croissant at the iconic Montauk Bake Shoppe (montaukbakeshoppe.com) or pick up an Italian breakfast of bomboloni and strong espresso at Montauk’s newest bakery, the sparkling Buongiorno (buongiornobakery.com). Drive or bike (rentals are available at montauksurfandsport.com) to Montauk Lighthouse (montauklighthouse.com), New York’s oldest. Then walk the trails around the building, taking in the thrilling sight of the Long Island Sound meeting the Atlantic. Don’t neglect the lighthouse’s museum, which has documents signed by George Washington and Thomas Jefferson attesting to the building’s pedigree.
For lunch with a view, order the catch of the day at Inlet Seafood (inletseafood.com), owned by a group of local commercial fishermen. Two miles east of the village is famed surf mecca Ditch Plains Beach, where you can watch wetsuit-clad surfers catching waves that get bigger through the fall and into the winter. Afterward, head back into town to shop for stylish beach souvenirs. Bontemps (bontempsmontauk.com), a new family-run shop, sells espadrilles made in France and sandals made in Greece. Destination Haus (destinationhaus.com) stocks home goods and accessories from near (large-scale prints of Montauk waves by photographer Laureen Vellante) and far (Moroccan blankets). In Montauk Harbor, Shipwreck (shipwreckmontauk.com) offers nautical-themed cameo jewelry made in Italy, macramé and shell dog collars, and glowing lamps that look like giant sea urchins and barnacles. In addition, owner Rebekah Harris runs silversmithing classes in the store’s own workshop.
Greenport has an increasingly cosmopolitan air, as trendy restaurants and boutiques compete with the town’s historical charms and natural beauty for visitors’ attention. To experience it all in a single day, begin with brunch at Bruce and Son (bruceandsongreenport.com), where the inventive and frequently changing menu might include strawberries and kefir cheese on sourdough toast or a grass-fed smash burger on brioche with pickled mayo.
There are many unique shops to explore. The constantly evolving Times Vintage (timesvintage.com) emits positive vibes with its large and well-curated collections of fashion, vinyl and home décor. Newcomer Popsicle and Finn (popsiclefinn.com) offers clothing, accessories and home goods from sustainable brands, and stunning surfing prints by photographer Joni Sternbach. At Kimberly Ruth Cavoores’ boutique wine shop One Kourt (onekourtwine.com), you’ll find wines from small sustainable vineyards across the globe, and a knowledgeable staff ready and willing to discuss them.
Mitchell Park encompasses 4 acres along the Greenport waterfront, and includes a boardwalk, a marina, a camera obscura and a working antique carousel. The North Fork boasts its own lighthouse, in the water off of Orient, known as Bug Light because of the spindly legs it used to stand on before its concrete foundation was poured.
Cruises to the structure, which run at 5 p.m. every Saturday through the end of October, leave from Greenport’s East End Seaport Museum (eastendseaport.org), steps away from the park.
Upon return, grab a dozen briny oysters at Little Creek Oysters (littlecreekoysters.com). For a more substantial meal, descend the stairs at speak-easy Brix and Rye (brixandrye.com) for cocktails and pizza, or perch at the bar at Noah’s (chefnoahs.com) for sophisticated seafood.