The North Fork’s best downtown is undoubtedly in historic Greenport Village.
Incorporated in 1838, Greenport boasts the area’s only deepwater harbor. Along with a rich maritime history, the small community prides itself on being a gathering place for talented local chefs, farmers, artists and crafters.
Whether you’re interested in shopping, cycling, fishing or unwinding and dining you’re sure to find plenty to do in the village.
It is easiest to follow this itinerary by car, but feel free to cut out the stops along the North Road if you’re hoofing it.
Start your day at Inlet Pond County Park, a mere 1.8 miles away from the village center, where hiking enthusiasts will find their oasis. Home to the North Fork Audubon Society, the 55-acre park offers 1.6 miles of trails that lead to Long Island Sound.
Making your way to the Inlet Pond observation platform, where the pond meets the beach, you’ll notice that the traffic noise fades, giving way to the sound of birds chirping and the Sound’s gentle waves. Running into friendly fellow hikers is not uncommon. While the peaceful walk is a joy in and of itself, the Audubon society’s Red House visitor’s center offers nature programs throughout the year.
After your walk, head back into town for brunch at Bruce’s Cheese Emporium & Café. Since opening in 1973, this Main Street spot has been a destination for diners seeking a true farm-to-table experience. On weekends, it’s easy to spot owner Scott Bollman and chef Eric Linker front and center serving up their bistro-style brunch menu.
To start, Bruce’s Bloody Mary could stand alone as an appetizer. Perfectly spiced, the brunch favorite is garnished with a reasonable portion of homemade candied bacon. But save room for the eats. The expansive menu offers something for everyone — from their one-of-a-kind French Press, served with Hampton’s Brine organic sauerkraut, to traditional buttermilk pancakes or a classic egg sandwich.
A proponent of locally sourced ingredients, Bollman seasons his recipes with North Fork Sea Salt, a company the North Fork native founded in 2011. Featuring a local tap beer and wine list, their outdoor patio is a perfect place for people-watching.
After brunch, a little wine tasting might be in order. Kontokosta Winery, just north and east of Main Street on the North Road, is the area’s easternmost tasting room and the only one with views of Long Island Sound. The modern facility opened in 2013 and has quickly gained a reputation as a favorite destination on the Long Island Wine Trail.
Then head back into the downtown area for some sights and shopping.
Walking through the harborfront village, you’ll notice plenty of places to pick up local provisions and handcrafted keepsakes. Art lovers will rejoice in the bounty of galleries, featuring acclaimed local artists. Those who know the value of a great vintage find will revel in exploring the distinctive items at the village’s many antique shops, such as The Times Vintage, which receives new inventory daily.
If you’re looking for a truly unique shopping experience, The Metal Monk on Front Street is worth a stop. Featured in major publications such as InStyle and O magazines, owner and artist Donya Lynn O’Brien is the visionary behind the jewelry line. Choose from popular affirmation bangles or make your own custom bracelet from their handcrafted charms.
Of course, taking in the sights along the waterfront, strolling the boardwalk at Mitchell Park and letting the kids ride on the historic 100-year-old carousel are must-stops along the way.
Now you have several choice options to pass the time until dinner.
There is Aldo’s coffee shop, where Sicily-born owner Aldo Maiorana blends custom roasts and serves up perfectly crafted lattes and what might be the best scones you’ll ever have in your life.
Nearby is the Little Creek Oyster Farm & Market. There is no better, or more delicious, example of Greenport’s working waterfront than the region’s first “U-Shuck” oyster joint.
All of their shellfish comes directly from local growers in sustainable quantities, meaning there’s always a chance you’ll discover a new variety each visit. Side effects of consuming these oysters may include increased joy and relaxation and, according to the menu, it may even help you tap into a hidden superpower.
On Carpenter Street, you’ll find the area’s first craft brewery, Greenport Harbor Brewing Co.
Before Greenport Harbor launched its tasting room in downtown Greenport, the North Fork was known exclusively as a wine region. Fast-forward seven years and there are five local craft brewery operations stretching from Greenport to Riverhead, including Greenport Harbor’s second location in Peconic.
Occupying a converted firehouse, the tasting room that started it all remains a staple in the village. Whether you’re there to grab a pint of their flagship American-style Harbor Ale or to enjoy a tasting flight, it’s hard to beat an afternoon at the brewery if you appreciate quality craft beer.
There are many great options for dinner, including Noah’s and The Frisky Oyster, as well as some of Greenport’s newest and hottest eateries — like American Beech.
The Stirling Square restaurant offers its own unique twist on New American fare and small plates. North Fork restaurateur Dennis McDermott and owner Brent Pelton breathed new life into a 100-year-old building, refurbishing the former barn into a modern restaurant and five-room luxury inn.
Of course, you don’t have to book a room to eat, but a reservation may come in handy during the summer months. Executive chef Arielle Ferrara’s simple, fresh and hearty cooking has made American Beech a customer favorite. Her buttermilk fried chicken and burgers topped with melted gruyère and garlic aioli are highlights of the menu, which she changes seasonally with the availably of market-fresh and local ingredients.