The South Fork of Long Island has a long legacy as a vacation spot for sophisticated, affluent visitors. It offers a splash of well-dressed people, St. Tropez style beach clubs, wineries that offer a fun social scene, farm stands that support the penchant for lovely in-home dinner parties, and boutiques that carry unique, high end fare.

Typically, when people think of the Hamptons they have an image of the South Fork in their mind. This stretch of Long Island, New York contains a series of quaint villages and gorgeous mansions that dot the land until it ends at Montauk. The most famed are West Hampton, Southampton, Bridgehampton, Sag Harbor, and East Hampton. There are many other smaller hamlets whose town centers are also worthy of seeing. However, if you have only one day, my personal favorite towns are Southampton, Bridgehampton, and Sag Harbor.

A good itinerary for a day trip to the South Fork would be to start in Southampton for some breakfast and morning shopping. Next, head to Bridgehampton to visit Channing Daughters Winery. Then, drive to East Hampton for lunch, strolling through the downtown, and do more shopping.  After that, I would circle back to Bridgehampton for an apéro glass of wine at Wölffer Estate’s Farm Stand and end with dinner in Sag Harbor before retiring home. There are many options available to you. I hope the suggestions below inspire you to visit.

South Fork Sag Harbor

“iu1428 Sag Harbor NY New York Long Island Custom House” image by Mark Goebel licensed under CC 2.0

Favorite South Fork Wineries

While the wineries in the South Fork make red, white, rosé, orange, sparkling wines and cider, I find their rosés, crisp whites, and Merlot most enticing. Most visitors go to the Hamptons during the warm late spring and summer months, making rosé a perfect fit for the Hamptons lifestyle.

While there are several wineries in the South Fork, they are much fewer than in the North Fork. To me, Wölffer Estate and Channing Daughters stand out.

 Wölffer Estate (Winery: 139 Sagg Rd, Sagaponack, NY; Farm Stand: 3312 Montauk Highway, Sagaponack, NY) – Owned by German born Christian Wölffer and situated near Bridgehampton, this vineyard is well known among New Yorkers for its prized Rosé, Merlot, and Chardonnay. Last year Wölffer came out with a new, slightly higher priced “Summer in a Bottle” rosé wine that has a gorgeous, artistic label, but for me tasted very similar to the slightly less expensive version. The winery is gorgeous and makes for quite a social scene during the summer. Stop by the Wine Stand on a Friday or Saturday and you will become part of the Hamptons scene. The wine stand is casual and from 5pm to closing on Friday and Saturday nights (May-October), there is live music. You are encouraged to bring your own chair or blanket.

South Fork Wolffer

“Wolffer Vineyard” image by Jiashiang licensed under CC 2.0

Channing Daughters (1927 Scuttle Hole Rd, Bridgehampton, NY) – Situated in the midst of Hamptons mansions, Channing Daughters is famed for its inventiveness and variety. Steered by the talents of James Christopher Tracy as winemaker, Mr. Tracy is known to plant varietals that nobody else plants in Long Island, such as Blaufränkisch, Lagrein, and Petit Verdot. As a trained chef and sommelier, Mr. Tracy is drawn to the culinary style of Fruili-Venezia Giulia. From this region, he draws inspiration to make crisp, beautiful whites from Sauvignon Blanc, Malvasia, and Chardonnay among others. Channing Daughters also offers a variety of different rosé styles, one of which is called Rosati. Also not to miss is a try at their orange wines.

South Fork Channing Daughters

“Channing Daughters” image by Joe Schlabtonik licensed under CC 2.0

Farm Products

Halsey’s Green Thumb (829 Montauk Hwy, Watermill, NY)Halsey’s Green Thumb specializes in organic produce and traces its roots back to 1644. They have an incredible display and offer a large variety of fresh produce.

Iacono Farm (100 Long Lane, East Hampton, NY) This is a chance to buy fresh eggs & chicken direct from the farm.

Favorite Boutiques and Stores

Hildreth’s (51 Main St, Southampton, NY)This is a prized Hampton store that sells wonderful home furnishing & accents, antiques, and children’s items. Hildreth’s is a great place to pick something up for you or as a gift.

Therapy Life & Style (33 Main Street, Southampton, NY) – Therapy Life & Style is a favorite women’s clothing that always offers something unique.

Loaves & Fishes Cookshop (2266 Montauk Hwy, Bridgehampton, NY) – This is an eye-catching store that you won’t miss even from your car as you drive along Rte. 27. They offer cooking and entertaining necessities, home goods, and accessories, as well as cooking classes.

Food Stores and Bakeries

The Village Cheese Shop (11 Main St., Southampton, NY) – This store is always packed with customers seeking wonderful cheese. They have an impressive display and a knowledgeable staff. Don’t forgo the sandwiches to go.

Goldbergs’ Famous Bagels  (stores in Mattituck, Westhampton, Southampton, East Hampton) – This bagel store has huge bagels that are “smashed”/flattened, nice, and crusty. They are thought of as the best bagel in the Hamptons.

Tate’s Bake Shop (43 N Sea Rd., Southampton, NY) – This is the famed cookie bakery whose green bag packaged cookies are now appearing in supermarkets. I still believe their chocolate chip cookie is their signature and the cookies are better at the actual store than from your supermarket. They also offer morning-baked goods like muffins and crumb cake.

Citarella (2209 Montauk Highway, Bridgehampton, NY) – This is a high-end food store with good take away and groceries. I am a big fan of their charcuterie and their cakes.

Pierre’s (2468 Main St., Bridgehampton, NY) – This is a lovely French bakery that has perfectly crumbly croissants just like in Paris.

Levain Bakery (354 Montauk Hwy, Wainscott, NY) – This is a lovely bakery known for its scrumptious brioche and cookies.

Cafes and Restaurants

 The Golden Pear Café (99 Main Street, Southampton, NY) – This casual café (bordering on a coffee shop) is centrally located. It is a cute Hamptons spot that is good for coffee, breakfast, or a quick bite throughout the day.  You may even spot a celebrity here.

Little Red (76-C Jobs Lane, Southampton, NY) – This casual café is great for lunch and dinner. It is typically bustling and offers good American fare.

Tutto il Giorno (56 Nugent St., Southampton & 6 Bay Street, Sag Harbor, NY) – This small chain restaurant hails from Tribeca (Manhattan). It offers a beautiful setting with delicious pastas and other Italian specialties. It is a wonderful restaurant for a nice lunch or dinner.  They also have a very nice outdoor seating area.

Nick & Toni’s (136 N Main St, East Hampton, NY) – This restaurant is a long time Hamptons icon. Often considered the best restaurant dining in the Hamptons, it will not disappoint you. It is very hard to get a reservation so make sure to call ahead well in advance. They have an incredible wine list.

Botwswick’s Chowder House (277 Pantigo Road, East Hampton, NY) – This is a café I love for its New England coastal feel. They specialize in seafood for either lunch or dinner. Dress casually.

The American Hotel Restaurant (45 Main St., Sag Harbor) – This is a historic Sag Harbor staple and is an upscale restaurant. Charm oozes from this hotel and restaurant. The outside of the hotel is draped in American flags and the inside features a lovely bar and restaurant. If you are not up for a meal (reservations recommended), visit the bar. They have an excellent wine list.

South Fork Bridgehampton Windmill

“Bridgehampton NY New York Long Island windmill” image by Mark Goebel licensed under CC 2.0

Looking to go to the North Fork of Long Island, too? Read about top wineries, restaurants, farm stands and more by clicking here and here.

NOTE: Guest Blogger, Aylin Amore, is the creative behind Mommelier, a blog that explores the vast world of wine, motherhood, cooking, and wine tourism. You may like to read Aylin’s previous guest post about visiting wineries in the North Fork of Long Island.

Cheers! ~ Cindy


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