1. Where to Stay
Be among the first guests at Cliffside Resort (from $375), a beachfront hotel opened July 4 weekend by East Hampton developer Ken Tedaldi. Cradled on bluffs overlooking the Long Island Sound, the 68 two-bedroom, two-bath suites come with wine refrigerators, balconies, on-site laundry, and access to a private beach. The Captain’s Roost, unit 207, has the best views of the sound.
The bright, contemporary Harbor Front Inn (from $299) is centrally located on the Peconic Bay beach and near downtown’s shops and restaurants. Book one of the oversize junior suites with a private balcony right on the bay, or splurge on the 800-square-foot terrace suite for the Jacuzzi tub, glassed-in shower, and a private patio with teak furniture.
Rent a cottage at the family-run, fifties-era Silversands Motel (from $300) and get an outdoor barbecue and picnic table on a quarter-mile stretch of private beachfront overlooking Shelter Island. Slips are available if you want to bring your boat.
2. Where to Eat
Start with a fresh lemon-mint mojito or extra-large margaritas for two at the bustling Frisky Oyster, where chef Hank Tomashevski serves a locally sourced, daily rotating menu heavy on seafood—think fresh grilled Montauk tuna or soft-shell-crab tempura—in a vintage-floral-patterned dining room. Reservations are scarce on weekends, but walk-ins for dinner are usually accommodated. Kids under 6 are not allowed.
VINe is the go-to spot for local wines by the glass. On Sundays, stop by for jazz brunch with a light menu of crêpes and quiche served on the grapevine-trimmed outdoor patio. This summer, owner Joe Watson will pour a different library wine by the glass—like the 1994 Harlan from Napa Valley—all day on weekends, a rare chance to try treasured wines on the cheap.
The dining room is often packed, so escape to the six-seater bar at the star-powered, country-chic North Fork Table & Inn. City expats Gerry Hayden (formerly of Amuse) and Claudia Fleming (formerly of Gramercy Tavern) serve locally sourced dishes like freshly plucked Peconic Bay scallops on a bed of asparagus risotto with smoky bacon and lemon confit.
3. What to Do
If you’re tired of the wineries, have a beer at the decade-old Blue Point Brewery in Patchogue. The tour ends with a pint of microbrew inside a converted seventies Penguin Ice Factory. Starting in July, the brewery co-sponsors Alive After 5, a Friday-night street fair featuring five stages of theater and local live music. Order a pint from the brewery’s stage, located on South Ocean Avenue this year.
Rent a bike ($28 a day) from Greenport’s Bike Stop (200 Front St.; 631-477-2432) and take it aboard a ferry to secluded Shelter Island ($5 round trip). Pick up a map at the visitor’s center and bike to the Mashomack Preserve ($2 donation suggested), a 2,039-acre woodland with twenty miles of trails. Break for lunch at André Balazs’s Sunset Beach Hotel (35 Shore Rd.; 631-749-2001), where you can eat the food of chef Dan Silverman (formerly of
Yoga arrived in Greenport only last May, at the Temple Yoga Center. The 3000-square-foot studio is housed in vaulted-ceiling former Masonic temple. Classes, $20 each or $18 each when you purchase a ten-class card, range from the standard Vinyasa and Ashtanga to teen yoga, prenatal and Mommy & Me.
Take the kids to Gull Pond Beach, a waveless strip next to the Shelter Island Ferry landing; you’ll need a $25 permit from the beach attendant. The more ambitious can drive to Orient State Park (Rte. 25; 631-323-2440; entry is $8 a day), the North Fork’s vast stretch of sand with a snack bar, bathhouse, picnic grounds, a playground, and miles of maritime forest for hiking, biking, and nature walks. Watch the sunset at 67 Steps, where a long staircase leads to a remote, cliff-enshrouded beach.
4. Insider’s Tip
If you’re carless, Winding Road Tours offer winery tours by bike from June through October or by appointment, leaving from Greenport’s Village Square (877-497-8687). The tour, which costs $175 to $220 per person, includes a catered lunch, tasting fees, and the option of riding in an air-conditioned van if you get too, er, tired. Bike rentals are available from Bike Stop in Greenport.
5. Oddball Day
Fuel up with an early breakfast of skillet fried eggs and bacon on the porch at Bruce’s Cheese Emporium and Cafe (208 Main St.; 631-477-0023). Pick up made-to-order sandwiches on your way out; you’ll need them aboard the Peconic Star II, a 90-foot party boat that will take you and 149 other passengers on a fishing trip and tour of the North Fork coastline. Learn to rig up from Captain Dave Brennan and his helpful crew. They provide rods and bait if you don’t want to buy them and will show you how to clean your catch (it’s porgies and fluke this time of year). If fishing’s not your thing, tan on the sun deck or dip into your cooler (the boat is BYO). Cool off with a mint-julep martini in the Frisky Oyster’s front lounge, just three blocks from the dock.
For restaurant recommendation and North Fork foodie news, check out Edible East End.
Lenn Thompson’s blog, Lenndeavours, has the best inside info on the local wine scene.