The town gem of Mitchell Park encompasses the Greenport Marina, the seasonal Greenport Carousel and the Ice Skating Rink. Families and couples congregate here for intimate afternoons or festive weekend events.
Front Street, Greenport, NY
As you drive out east from the City, the land mass of Long Island splits in two: on the South Fork are the tony towns of East Hampton and Montauk; on the North Fork, farmland and wineries unscroll all the way to ocean. This is pastoral Americana fueled in recent years by creative folks looking to get back in touch with the land. At the tip of it all is the town of Greenport, which for four centuries has drawn pioneering settlers whom today we’d call entrepreneurs and influencers. No one comes to this fishing town to see and be seen. You come to unplug, to reconnect, to take pleasure in life’s little, magical moments, like extracting the last piece of knuckle meat from a freshly-caught crab or spotting the constellations beside a beachfront fire. Stop by to have a look, or, better yet, participate. Leave the air kisses to the other fork; on the North Fork, we’re keeping it real.
Shelter Island is both a town and an island at the eastern end of Long Island; of its 8,000 acres, nearly one-third is owned by The Nature Conservancy to be preserved in perpetuity. Hop the ferry and hang out for a day to bird-watch, bike-riding, and check out the beautiful houses that line the quiet streets.
The ferry has connected this eastern point of Long Island to New England for more than a century, and the depot is just a 15-minute drive to Greenport. At this terminus of the North Fork, you can also spy four lighthouses from the Orient Beach State Park.
Main Road, Orient, NY
Walk along wetlands, ferns, and fauna as osprey soar above on a never-ending quest for fish to eat in the Pond. The peaceful preserve is a favorite spot for hiking and walking through the coastal marine ecosystem, with its woodlands, meadows, vernal ponds, and tidal wetlands—not to mention 2,200 linear feet of shoreline.
Chapel Lane, Greenport, NY
For four centuries the town of Greenport has drawn pioneering settlers whom today we’d call entrepreneurs and influencers. No one comes to this fishing town to see and be seen. You come to unplug, to reconnect, to take pleasure in life’s little, magical moments, like extracting the last piece of knuckle meat from a freshly-caught crab or spotting the constellations beside a beachfront fire. Stop by to have a look, or, better yet, participate.
As you drive Out East from the City, the land mass of Long Island splits in two; on the South Fork are the tony towns of East Hampton and Montauk, on the North Fork, farmland and wineries unscroll all the way to ocean. This is pastoral Americana fueled in recent years by creative folks looking to get back in touch with the land. Leave the air kisses to the other fork; we’re keeping it real.
You’d think you were in Grasse, the fragrance is so intoxicating here. At the largest lavender farm in America, the high-quality herb is grown in abundance, ready to be taken home as dried satchels, in honey, or in bouquets. Just walking the fields is magical on a sunny afternoon.
540 Main Rd., East Marion, NY
Established in the mid-1940s, Sang Lee is now a second-generation farm specializing in Asian produce and heirloom tomatoes and herbs. Along with fresh radishes and cabbages, the Lees sell gardening supplies, organic non-GMO seeds and plants, and prepared foods for a robust picnic. Karen Lee is often around to give tastings and tours.
25180 County Rd. 48, Peconic, NY
8 Hands aims to connect customers to the land, offering them access to the farmer, the livestock grazing the 28-acre pastures, and the herb garden. Pick up essentials like grass-fed meats, pastured eggs, homegrown produce, and woolens from the onsite flock of Icelandic sheep.
4735 Cox Ln., Cutchogue, NY
Take a break from all the wineries and head to the original beer-tasting room in Peconic. Along with live music and seasonal brews on tap and in bottles, the Peconic location just opened a restaurant featuring Chef Vincent Purcell’s beer-battered cod and beer-brined chicken.
42115 Main Rd., Peconic, NY
Aldo Maiorana has been roasting coffee and baking his beloved hand-crafted biscotti and scones since 1987 at his old-world-style café. You will be forgiven for thinking you’ve stepped out of a 1940s Havana coffeeshop.
103-105 Front St., Greenport, NY
The unassuming restaurant won a James Beard Award for Best Chef in the Northeast, yet it remains unstuffy. Much of the staff hails from Gramercy Tavern, so expect elegance but comfort in dishes like sake-poached Peconic Bay scallops and confit of pork belly. Don’t miss dessert: Claudia Fleming is a recipient of Beard’s coveted pastry chef of the year.
57225 Main Road, Southold, NY
Well-known New York City chefs (like Tom Colicchio) source their clams all the way out here, so you know they are the finest. Also delicious: local fillets, whole fish, frozen soups, party platters, and anything else you need to get the party started (including beer). Owner Charlie Manwaring has been doing this for 25 years; he knows his stuff.
64755 NY-25, Southold, NY
This neighborhood hangout is all about the cocktails, especially classics mixed up with housemade amaros and tinctures and bitters. The beer selection is also impressive, and don’t forget the creative pizzas to keep some carbs in that stomach. You’re guaranteed to run into a shopkeeper or some other new friend you just met in town.
308a Main Street, Greenport, NY
A tree of the same name has grown in nearby Stirling Square for the past 75 years, so why not borrow its name for this 19th-century stable that’s been converted into a restaurant, bar, and hotel? The five suites sit above a modern, clean dining room that specializes in local farming, aquaculture, and viticulture, which means you can expect seasonal vegetables and fish, and only the best wines to go with them.
300 Main Street, Greenport, NY
Chat up the baristas at this charming coffee shop where everyone takes their daily cup of joe seriously and pastries are brought in fresh throughout the day. Ask to see the onsite roaster if you aren’t convinced that this is a mecca of beans.
55795 Main Road, Southold, NY
Expect the unexpected at this artisanal, brick-oven pizza parlor, which gains inspiration from a circa-1943 food truck known as Rolling in Dough—a novelty that (according to legend) turned former GIs onto pizza on this side of the Pond. Try the doughy stuff, or dig into a salad paired with a crisp wine.
308 Main Street, Greenport, NY
Authentic Mexican comes to Greenport at this Baja-style taqueria and tequila bar. Take a seat beneath the colorful décor and images of famous wrestlers (from where the restaurant gets its name) and dive into carne asada tacos, nachos, and Tex-Mex favorites like shrimp burritos. Not in the mood to eat? Grab a seat at the handmade bar and order up endless rounds of margaritas.
119 Main St, Greenport, NY
What began as a wheelhouse of a whaling ship in the late 1800s is now part of a shuch-your-own oyster shop in the heart of historic Greenport. Eat in, or take a few dozen home for a sensual (and super-fresh) feast.
37 Front Street, Greenport, NY
The North Fork’s most popular center for yoga, pilates, and organic juice offers daily classes for all levels of practice with multiple styles of yoga. The Giving Room Market is also known for its freshly-pressed organic juices made from seasonal produce procured from local farms.
56215 Main Road, Southold NY
For anyone looking to decorate the walls of her home, this gallery represents artists that span disciplines and styles. Set in the former Town Hall of Greenport, South Street Gallery is hung with landscapes, abstract works, and lots of images that reflect the maritime past and present of the North Fork.
18 South Street, Greenport, NY
They specialize in canvas goods like awnings, tents, umbrellas, and shelters, but locals love the family-run business for sails, sun tops, and covers for boats of any size. You can expect top-tier craftsmanship and personalized service at this fifth-generation mainstay.
74100 Main Road, Greenport, NY
Husband-and- wife owners Virginia McFadden and Kenneth Ludacer are pioneers in these parts, drawing city folk to their antiques shop for 25 years. Their endless quest for unusual mirrors, framed prints, furniture, repurposed garden objects, and architectural finds make them a must-stop shop for architects and designers working on projects in the area and beyond.
430 Main Street, Greenport, NY
You can rent a paddle board here in season, but you can also ask the clerks for the best spot to catch some wind or what live music is playing that weekend. Immersed in a beachy vibe, the shop sells clothing, sun and beach accessories, jewelry…even GoPros and ukuleles. Even if being on the water isn’t your jam, it’s worth a pop by to understand the appeal of this neck of the woods.
211 Main St., Greenport, NY
The lifestyle boutique in the heart of Greenport emphasizes craftsmanship and artistry through gifts and home accents that are handmade onsite using reclaimed wood, metal, textiles, and botanicals. Stop by to pick up signs showing the coordinates of the North Fork, repurposed silverware, leather satchels, and hand-dipped candles all sourced by husband-and-wife team Jason & Rena Wilhelm.
41 Front Street, Greenport, NY
The women’s clothing store specializes in resort wear, jewelry, accessories, and anything else world-traveler Heidi Kelso can dig up on her jaunts to Thailand, Bali, and India. Her gypset sensibility translates into a sophisticated, carefree style that fits in perfectly with the North Fork aesthetic.
132 Main Street, Greenport, NY
Set in the 1909 Suffolk Times Newspaper Building, the warehouse stocks gently-loved pieces of art, fashion, and furnishings. Stop in to find 1960s frocks, old-fashioned typewriters, Brownie cameras, jewelry, figurines, and other hand-selected, collectible memorabilia.
429 Main Street, Greenport, NY
When the tasting room opened in Greenport 2009, it was one of the first breweries in this wine-centric region. Now John Liegey and Rich Vandenburgh have added to their roster a 13,000-square-foot facility in Peconic, with a restaurant as well as a brewery. Look for a stone fireplace and film screenings to be added during the summer months.
234 Carpenter St., Greenport, NY and 42115 Main Road, Peconic, NY
What started as a small 12-acre operation in 1992 has grown into a collective of diverse winemakers who work with veteran vintner Russell Hearn to produce wines that will knock your socks off. If you had to pick one, try the Reserve Pinot Blanc, made with 30-year-old vines, and named one of the top 12 wines in America by the Wall Street Journal. And yes, it’s all grown sustainably.
13050 Oregon Rd, Cutchogue, NY
Don’t expect to see limos or buses at this intimate winery; only 8 guests are allowed to visit the boho-chic space at a time, and the only wine on offer is a stellar rosé. It all started in 2014 when owners restored a 1977 Citroen van from Normandy and began selling bottles roadside. Now they introduce a select volume of bottles in March, and all are gone by Christmastime.
1450 S Harbor Rd, Southold, NY
The North Fork’s first (and only) waterfront winery stands on 62 acres of bluffs and coastline where guests are encouraged to purchase vintages, sure, but also to sample family-made blends in the midst of agrarian bliss. Have a chat with a member of the Kontokosta family, who torture and nurture their vines in order to create the most interesting wines in the region. Also, the whole place is wind-powered—a novelty anywhere, even here.
825 North Rd, Greenport, NY