Southold,
Southold is a charming town located on the eastern end of Long Island, New York. It is known for its historic buildings, scenic vineyards, and picturesque beaches along the Long Island Sound. Visitors can explore the town's quaint shops, dine at local seafood restaurants, and enjoy outdoor activities such as kayaking and biking.
Southold's rich maritime history and beautiful landscapes make it a popular destination for both tourists and residents alike.
Day plans
Spend a day exploring around
Exploring the Outdoors
morning:Start your day with a scenic hike at Cedar Beach County Park to witness a breathtaking sunrise over the waters. Proceed to take a leisurely walk through the historic Greenport Village. Stop by for a delicious breakfast at Bruce & Son.
afternoon:Head to Orient State Park for a relaxing picnic by the beach and enjoy a kayaking adventure along the serene coastline. Visit Lavender By the Bay to immerse in the beauty of lavender fields and indulge in some lavender-infused treats.
evening:Experience an authentic farm-to-table dining at North Fork Table & Inn, followed by a delightful evening stroll at Horton Point Lighthouse Park.
Cultural Immersion
morning:Begin your day with a visit to Southold Historical Society to delve into the rich history of the region. Indulge in a delightful brunch at The North Fork Table & Inn, known for its refined culinary offerings. Explore local art galleries and boutiques in the downtown area.
afternoon:Savor a wine tasting tour at renowned wineries such as Raphael, Bedell Cellars, and Old Field Vineyards. Enjoy the picturesque vineyard landscapes and sample the finest wine selections.
evening:Conclude your day with an evening of live music and entertainment at Greenport Harbor Brewing Co. and celebrate the vibrant local arts scene.
Culinary Delights
morning:Embark on a culinary adventure starting with a visit to The Lenz Winery for a delightful wine tasting experience. Enjoy a delectable farm-to-table breakfast at 8 Hands Farm. Explore the charming village of Greenport and its local artisans.
afternoon:Indulge in a culinary tour featuring local specialties such as fresh oysters from Little Creek Oyster Farm and artisanal cheeses from Catapano Dairy Farm. Satisfy your sweet tooth at the famous North Fork Chocolate Company.
evening:Treat yourself to a seafood extravaganza at Claudio's Restaurant, an iconic waterfront eatery, and savor the freshest local catches of the day.
Relaxation and Wellness
morning:Kick-start your day with a rejuvenating yoga session at North Fork Yoga Shala. Nourish your body with an organic brunch at The Halyard restaurant, overlooking stunning waterfront views. Take a serene walk along the scenic Soundview Beach.
afternoon:Indulge in a unique wellness experience at Lavender By The Bay, offering relaxation amidst fragrant lavender fields and holistic aromatherapy treatments. Unwind with a therapeutic massage at a local spa for complete relaxation.
evening:Experience tranquility with a sunset meditation at Goldsmith Inlet Park and embrace the serenity of the natural surroundings.
Southold Famous Food
Must-Try local dishes
Lobster Roll
A quintessential local favorite, the lobster roll features succulent chunks of fresh lobster meat tucked into a buttered, toasted roll. It can be savored at places like Southold Fish Market or Little Creek Oyster Farm & Market.
Must-Try!
Oyster Tasting
Southold's waters are renowned for producing some of the finest oysters. Visitors can indulge in an oyster tasting experience at Little Creek Oyster Farm & Market or Widow's Hole Oyster Farm.
Duck Breast with Local Berry Sauce
This dish showcases the region's seasonal berries paired with tender duck breast, often featured on the menu at North Fork Table & Inn.
Photography Spots in Southold
Locations for the best views and photo opportunities
Harborfront Park
Offers beautiful views of Peconic Bay and sailboats, as well as a fishing pier and picnic area for photo opportunities.
Horton Point Lighthouse
Provides stunning views of Long Island Sound and features a historic lighthouse, making it a great spot for scenic photos.
McCabe's Beach
Known for its picturesque beach views, dunes, and sunsets, making it ideal for photography and capturing the natural beauty.
Seasonal Advice
Best times to visit and what to expect in different seasons
Spring
Best time to visit Southold, United States. Pleasant weather and blooming nature. Ideal for outdoor activities and enjoying the scenic beauty of the region.
Summer
Peak tourist season with warm weather, perfect for beach activities and water sports. Various events and festivals take place during this time.
Fall
Beautiful foliage and harvest season. Perfect time for wine tasting and exploring local farm stands. Mild weather and fewer crowds.
Winter
Quieter period with cold weather. Great for cozy getaways and exploring the local charm of Southold. Some wineries and attractions may have reduced hours.
Food Markets & Street Food
A food market and street food guide
Greenport Farmers' Market
Located nearby, this market offers a delightful array of local produce, artisanal goods, and gourmet treats, making it an ideal spot to savor fresh flavors and pick up picnic supplies.
Food Trucks at Love Lane
Visitors can explore an assortment of food trucks offering culinary delights ranging from gourmet grilled cheese to wood-fired pizza, creating a vibrant street food scene close to the heart of Southold.
Pet sitters in Southold
Relax and unwind while your furry friend enjoys making a new companion!