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While Southold sometimes gets overlooked in favor of its neighbor to the east, the Village of Greenport, or points west that are closer to home for many visitors to this region, it remains a prime destination for people looking to escape New York City and plant new roots in the country. You barely even need to step on land to experience all the hamlet has to offer. The still waters of Southold Bay and Jockey Creek become open highways for boaters and office spaces for fishermen. And Long Island Sound in Southold is home to Horton Point Lighthouse, a landmark worth checking out for both its history and its serene setting.


53930 Main Rd., Southold

Southold Opera House

Hosts live semiannual opera events.

631-407-8001 •



Cedar Beach County Park

Open to Suffolk County Green Key holders, it’s at 3690 Cedar Beach Road, Southold, facing Shelter Island Sound. Boat-launching ramp and no fees. Shoreline maintained by Cornell Cooperative Extension. Gates close at sundown.

631-765-1800 •


Goldsmith Inlet Beach

Parking permit required, it’s at the end of Mill Road, Peconic, on L.I. Sound, along west side of Goldsmith Inlet, opposite county park. Swimming; no lifeguard.

631-765-1800 •


Goose Creek Beach

Parking permit required off North Bayview Road, Southold, on Southold Bay. Swimming, playground, restrooms; lifeguard in season.

631-765-1800 •


Kenney’s Beach

Parking permit required on Kenney’s Road, Southold, on L.I. Sound. Swimming, restrooms, lifeguard in season.

631-765-1800 •


McCabe’s Beach

Parking permit required on North Sea Drive, Southold, on L.I. Sound. Swimming, restrooms, lifeguard in season.

631-765-1800 •


Norman E. Klipp Park (Gull Pond)

Parking permit required at the end of Manhanset Avenue, Greenport, on the bay overlooking Shelter Island. Playground and lifeguards in season. Boat-launching ramp, parking by town permit only.

631-765-1800 •


Town Beach

Parking permit required on Route 48 (North Road), Southold, on L.I. Sound. Swimming, playground, picnic area, restrooms. Handicapped-accessible, with wheelchairs available in season. Lifeguards and attendants in season.

631-765-1800 •


56275 NY-25, Southold

Blue Duck Bakery

631-629-4123 •

55765 Main Rd, Southold

Country Corner Cafe

631-765-6766 •

50 North Sea Dr., Southold

Elbow East

765-1203 •

55500 Main Road, Southold

Founders Tavern

765-3100 •

55750 Main Rd., Southold

Grace & Grit

876-5521 •

55700 Main Road, Southold

Grateful Deli

765-6408 •

46455 Route 48, Southold

La Cascada

765-8708 •

53345 Main Rd., Southold

Latin Fuzion

407-5600 •

54195 Main Rd., Southold

Maroni Cuisine

757-4500 •

41150 County Rt. 48, Southold

North Fork Shack

876-5566 •

44780 Route 48, Southold


765-2111 •

55575 Main Road, Southold

Wayside Market

765-3575 •

Farm Stand

3005 Youngs Ave., Southold

The Farm Beyond

631-416-0075 •

Historic Sites

3575 Lighthouse Road, Southold

Horton’s Point Lighthouse

This Southold landmark was commissioned in 1790 by George Washington — though it wasn’t constructed until 1857 — and is listed on both the national and state registers of historic places. Explore the nautical museum and visit the 58-foot tall tower for a panoramic view of the Long Island Sound and the surrounding park. Outside...

631-765-5500 •

1115 Main Bayview Road, Southold

The Custer Institute and Observatory

The institute is the oldest public observatory on Long Island. Every Saturday from dusk until midnight the volunteer staff gives guided tours of the facilities and the night sky with the help of its powerful telescopes. There are also frequent lectures, classes, concerts, art exhibits and other special events throughout the year. 1115 Main Bayview...

631-765-2626 •

55200 Route 25, Southold

The Southold Historical Society Museum Complex

The Maple Lane complex is home to 11 historic buildings maintained by the Southold Historical Society. Walk the grounds to discover highlights such as The Thomas Moore House and the Ann Currie-Bell House, which is listed on the state and national registers of historic places.

(631) 765-5500 •

Horseback Riding



62300 Main Road, Southold

Heron Suites

631-765-5121 •

54300 Route 48, Southold


631-765-1570 •

565 South Harbor Road, Southold

South Harbor Inn

646-552-5047 •

47100 Route 25, Southold

Vine + Sand

631-620-9253 •


Parks, Preserves, and Camping

Main Road, Southold

Paul Stoutenburgh Preserve

Shoreline frontage on Arshamomaque Pond (Mill Creek), tidal salt marsh meadows, woodlands, vernal freshwater ponds and wetlands. Hiking year round, dawn to dusk.

631-765-1800 •


54127 Main Rd, Southold

Arni Paperie

718-483-6054 •

53345 Main Rd, Southold



41965 Main Rd, Peconic

In the Attic Too

631-605-9439 •

53345 Main Rd, Southold

One For All

516-586-2894 •

Feather Hill Village 53345 Main Rd, Southold

Satnick Jewelers

516-695-0638 •

54796 NY-25, Southold

Southold Ace Hardware

631-779-2676 •

53740 Main Rd, Southold


631-765-8455 •

53995 Main Rd, Southold

White Flower Farmhouse

631-765-2353 •

Spas, Salons & Barbers

53155 NY-25, Southold

Main Roots

(631) 407-5700 •

56475 Main Rd Building B, Southold

Salone Dei Capelli

(631) 765-6363 •

Tour Boats


Fish North Fork

Let Captain Mark Melnick take you and your guests for a leisurely private three-hour tour that circumnavigates scenic Shelter Island aboard the Emily Rose, a semi-custom Judge Yachts 27 Chesapeake. There is also a plan-your-own option for a customized excursion, from a family sightseeing tour of the North Fork to a bachelorette party. Reservations are...

631-204-8150 •


1450 South Harbor Road, Southold

Croteaux Vineyards

Croteaux Vineyards, located in Southold, New York, is the only vineyard in the United States that is exclusively dedicated to growing vinifera grapes for producing Provence-style rosé wines. Planted in 2003, our vineyards and tasting garden are set against the backdrop of two historic farms that have been in continuous agricultural production since the 1700s....

44535 Route 25, Southold

Duck Walk Vineyards

This vineyard’s Southold location, with its spacious, vaulted tasting room, accommodates large groups and celebrations. It’s also a dream ambiance for a wine country wedding, providing the perfect setting for your special day. Conveniently located near fine dining in Southold and Greenport, Duck Walk North features wine accompaniments and offers local craft beer on tap....

631-726-7555 •

46005 Main Road, Southold

Mattebella Vineyards

Visit this Southold winery for an intimate and educational tasting experience through a combination of excellent wines, beautiful surroundings and delicious finger foods. From the vegetable and fig gardens — as well as the plethora of roses and hydrangea herb gardens — nature is incorporated into every element at Mattebella Vineyards. The certified sustainable farm...

631-655-9554 •

5195 Old North Road, Southold

One Woman Wines & Vineyards

Those seeking an intimate winery experience away from all the crowds should visit this tiny, rustic tasting room in Southold. One Woman Wines & Vineyards is a quintessential North Fork tasting room that’s less than 160 square feet and doesn’t allow large groups or limos during business hours. Despite the tasting room’s size, customers experience...

631-765-1200 •

39750 Route 48, Southold

Sparkling Pointe Vineyards and Winery

The vision of vintners Cynthia and Tom Rosicki, Sparkling Pointe encompasses 40 acres of sustainably grown vineyard planted with the classic Champagne grape varietals — pinot noir, pinot meunier and chardonnay. Using strictly the traditional Methode Champenoise process, Sparkling Pointe is the only winery on the North Fork to produce exclusively sparkling wines. The wines...

631-765-0200 •

59600 Main Road, Southold

The Old Field Vineyards

Sip on handcrafted wines while enjoying the view of 1850s buildings and wonderful, old shade trees at this Main Road winery. The Old Field Vineyards in Southold features a tasting bar with a laid-back atmosphere and doesn’t permit buses or groups over 10 people.  Five family members run the micro-operation to create premium red, white,...

631-765-0004 •

59600 Main Road, Southold


Varieties: merlot, cabernet franc, pinot noir, sauvignon blanc, chardonnay Sip on handcrafted wines while enjoying the view of 1850s buildings and wonderful, old shade trees at this Main Road winery. The Old Field Vineyards in Southold features a tasting bar with a laid-back atmosphere and doesn’t permit buses or groups over 10 people. Five family...

631-765-0004 •

45470 Route 25, Southold

The Tap Room at Corey Creek

The Tap Room at Corey Creek is a new way to experience the best wines Bedell has to offer. The Southold establishment serves limited runs of small-batch, hand-crafted and sustainable wines on tap and also offers wines by the bottle and in growlers. Winemaker Richard Olsen-Harbich was among the first on the East Coast to...

631-765-4168 •