Southold, NY, is a charming town located on the North Fork of Long Island. Known for its beautiful landscapes, rich history, and coastal beauty, Southold offers a unique mix of fun activities for everyone. Whether you enjoy the great outdoors, visiting local shops, or tasting delicious food, there is something for you to enjoy in this lovely area.
In this guide, we will be looking at some of the best things to do in Southold. From scenic parks and beaches to exciting events, there’s no shortage of adventures waiting for you. Grab your friends and family, and get ready to make wonderful memories in this delightful town!
Things to Do in Southold NY
1. Visit Sparkling Pointe Vineyards & Winery
Sparkling Pointe Vineyards & Winery is a must-visit for wine enthusiasts. Known for its award-winning sparkling wines, this winery offers a delightful experience. Guests are welcomed to sip on fine wines while taking in stunning vineyard views.
You can enjoy guided tours of the winery, where staff share insights into the winemaking process. This immersive experience gives visitors a deeper appreciation for sparkling wines. Don’t forget to try their signature bubbly; it’s a local favorite!
The outdoor seating area provides an inviting atmosphere to relax with friends and family. It’s the perfect spot to savor a glass of wine and enjoy the beautiful landscape. Make sure to check their schedule for special tasting events and live music.
Whether you are a wine connoisseur or a casual drinker, the experience is enjoyable for everyone. Sparkling Pointe truly embodies the craftsmanship and artistry of winemaking. It’s a delightful escape that enhances the charm of Southold.
Make your day memorable with a visit to Sparkling Pointe. You won’t want to miss this gem on the North Fork.
Address: 39750 County Rd 48, Southold, NY 11971.
2. Relax at Croteaux Vineyards
Croteaux Vineyards is an oasis of tranquility in Southold. Specializing in rosé wines, this vineyard invites guests to enjoy tastings in a picturesque garden setting. The peaceful ambiance is perfect for unwinding with loved ones.
Visitors can take part in guided wine tastings, where they sample their exquisite rosés. The knowledgeable staff guides you through each sip, explaining the unique flavors and aromas. It’s an educational experience paired with delicious wine.
The vineyard features beautiful gardens and outdoor seating, making it an ideal spot for a picnic. You can grab a bottle of your favorite wine and relax among the vines. The scenery is perfect for capturing memorable photos.
Throughout the summer, Croteaux often hosts events and wine festivals. These gatherings create a fun atmosphere for all visitors. Live music often accompanies the delightful tastings, enhancing your experience.
Make a stop at Croteaux Vineyards for a unique and relaxing experience in Southold. The winery’s charm will leave a lasting impression.
Address: 1450 S Harbor Rd, Southold, NY 11971.
3. Explore The Old Field Vineyards
At The Old Field Vineyards, you can immerse yourself in nature and fine wine. This charming vineyard offers a variety of tastings, allowing guests to explore different wine styles amidst beautiful scenery. The rustic ambiance adds to its appeal.
With its scenic views of the vineyard and surrounding landscapes, you’ll enjoy sipping quality wines outside. It’s the perfect escape to relax and enjoy a sunny afternoon. Bring a blanket for a picnic and make it a fun, leisurely day.
The knowledgeable staff guides you through the tasting experience. They provide insights about each wine, enhancing your appreciation for the craft of winemaking. It’s a truly educational journey for wine lovers.
Check out their seasonal offerings and special events. The vineyard often hosts wine and food pairings that highlight local flavors. Each event promises to be memorable, blending cuisine with the exceptional wines produced right there.
Don’t miss The Old Field Vineyards during your visit to Southold. It’s a perfect blend of relaxation, enjoyment, and beautiful scenery.
Address: 59600 County Rd 48, Southold, NY 11971.
4. Tour the Horton Point Lighthouse Nautical Museum
The Horton Point Lighthouse Nautical Museum is a must-see for history buffs. Built in 1857, it stands as a historic landmark overlooking the stunning Long Island Sound. The museum offers a glimpse into maritime history and the lighthouse’s significant role.
Visitors can climb to the top of the lighthouse for panoramic views of the coastline. The climb is worth it, providing breathtaking scenes and amazing photo opportunities. The lighthouse itself is beautifully preserved, making you feel like you’ve stepped back in time.
Inside the museum, you’ll discover fascinating maritime exhibits. These displays detail the lighthouse’s history and its influence on navigational safety. Friendly staff are available to answer questions and share stories about the area’s nautical past.
After your tour, enjoy the surrounding park area. It’s a peaceful place for a stroll and offers beach access. The scenic views of the water and nearby landscapes create a perfect backdrop for relaxation.
Make sure to visit the Horton Point Lighthouse during your Southold adventures. It’s a living piece of history waiting to be explored.
Address: 3575 Lighthouse Rd, Southold, NY 11971.
5. Embark on the Southold Town Milestone Tour
The Southold Town Milestone Tour is a delightful walking journey through history. This self-guided tour takes you past 19th-century milestones along the former King’s Highway. It’s an engaging way to explore Southold’s rich heritage.
As you walk, you’ll encounter historical markers that showcase the area’s past and the importance of these milestones. Each stop tells a unique story, highlighting significant moments in Southold’s fascinating history.
The tour is perfect for families and history enthusiasts alike. You can take your time and admire the beautiful scenery as you stroll. This experience combines education with enjoyment, making it a fun day out.
The local tourism office provides maps and information to help guide you. They also offer insights into notable landmarks along the route. It’s a great way to learn while immersing yourself in Southold’s charm.
Plan a day to take the Southold Town Milestone Tour. It’s an enriching experience that connects you with the local history and stunning landscapes.
Address: 54325 Main Rd, Southold, NY 11971.
6. Discover the Maple Lane Complex
The Maple Lane Complex is a hidden treasure for those interested in history. Managed by the Southold Historical Society, this site features 11 historic buildings. Each building tells a different story about Southold’s rich past.
Visitors can take guided tours that offer insights into local history. The tours explain how each building contributed to the community. These include a schoolhouse, a barn, and other structures that showcase early life in Southold.
During your visit, take time to explore the beautiful grounds. The property is well-kept and provides a lovely setting to enjoy the outdoors. You can stroll through the gardens and take in the peaceful surroundings.
The site often hosts events and activities for visitors of all ages. This includes workshops, exhibits, and family-friendly programs throughout the year. These events make it a lively hub for community engagement.
Don’t miss the opportunity to discover the Maple Lane Complex. It’s a fantastic way to step back in time and appreciate Southold’s history.
Address: 54325 Main Rd, Southold, NY 11971.
7. Hike at Arshamomaque Pond Preserve
Arshamomaque Pond Preserve is a serene escape for nature lovers. With scenic trails winding through woodlands and salt marshes, it’s ideal for hiking. Visitors can connect with nature while exploring various habitats.
The trails are well-maintained, making them accessible for all skill levels. Casual walkers and seasoned hikers alike will find beauty at every turn. Birdwatching and wildlife spotting are popular activities in this natural oasis.
As you hike, look out for local flora and fauna. The diverse ecosystem is home to various bird species, making it a beautiful spot for photography and observation. Bring your binoculars to catch a glimpse of the wildlife!
Plus, the peaceful surroundings make it an excellent place to reflect and unwind. Enjoy a picnic amidst the natural beauty after your hike. There are picnic areas available for guests to enjoy lunch in the fresh air.
Take a trip to Arshamomaque Pond Preserve for a refreshing outdoor experience. It’s a wonderful way to enjoy the beauty of Southold’s nature.
Address: 1225 Oregon Rd, Southold, NY 11971.
8. Birdwatch at Ruth Oliva Preserve at Dam Pond
The Ruth Oliva Preserve at Dam Pond is a premier destination for birdwatching. Situated along the water’s edge, this preserve offers trails perfect for spotting a wide variety of birds. Nature enthusiasts will enjoy exploring this beautiful habitat.
Visitors can walk alongside the scenic waterfront area, which provides excellent viewing opportunities. Bring a pair of binoculars and a camera to capture the colorful birds in action. The preserve is home to numerous species, making every visit unique.
In addition to birdwatching, this spot is perfect for leisurely walks. The serene environment invites you to slow down and appreciate the beauty of nature. The views of the pond are picturesque, creating a tranquil setting.
Whether you are an experienced birder or new to the hobby, the preserve provides a wonderful experience. Educational signs along the trail offer insights into the local ecosystem and its inhabitants.
Visit the Ruth Oliva Preserve for a peaceful day of birdwatching and nature. It’s a hidden gem in Southold that every nature lover will appreciate!
Address: Dam Pond, Southold, NY 11971.
9. Experience Southold Bay Oysters Farm Tours
Southold Bay Oysters offers a unique opportunity to learn about local aquaculture. Their farm tours are engaging and educational, presenting the fascinating world of oyster farming. You’ll gain insights into the process of raising oysters in the pristine waters of Southold Bay.
During the tour, guests can participate in oyster tastings. This delicious experience pairs fresh oysters with local wines, creating a delightful culinary adventure. Each bite showcases the savory flavors and textures of the region’s seafood.
Guided by knowledgeable staff, you will discover how oysters contribute to the ecosystem. They are not only a delicacy but also vital to maintaining healthy waters. This educational approach enhances your appreciation for these amazing shellfish.
If you’re a seafood lover, this experience is a must! Gather your friends or family for a fun day out on the water. Engaging tours and tastings promise to be a highlight of your visit.
Book your Southold Bay Oysters farm tour today for an unforgettable marine adventure. It’s a unique way to connect with the local environment!
Address: 24800 Main Rd, Southold, NY 11971.
10. Visit East End Lighthouses
Exploring the East End Lighthouses is a charming addition to your Southold visit. These historic landmarks reflect maritime history and the beauty of the coastline. Each lighthouse has its own unique character and history to discover.
Orient Point Lighthouse and Horton Point Lighthouse are two key highlights. Both offer scenic water views and spectacular photo opportunities. A visit to these lighthouses creates a memorable experience for all visitors.
Some lighthouses allow limited access for tours, while others can be admired from a distance. Make sure to check their schedules for guided visits or special events. Each lighthouse has stories to tell about ship navigation and historic safety.
Additionally, the coastal landscapes surrounding these lighthouses are stunning. Bring a picnic to enjoy while soaking in the breathtaking views. It’s a great way to appreciate the maritime culture of this area.
Make a day of exploring the East End Lighthouses to enrich your Southold experience. The lighthouses stand as symbols of history and beauty along the North Fork.
Address: Orient Point Lighthouse, 1110 Coast Guard Rd, Orient, NY 11957.
11. Explore Fort Corchaug
Fort Corchaug is an intriguing archaeological site in Southold. This 17th-century Native American fort offers visitors a chance to step back in time. Much of the historic site remains, revealing the layout of the original fort.
Visitors can walk the grounds, exploring the remains of the fort’s structure. Informative plaques provide context and history of the Native American tribes who once inhabited this area. It’s an enlightening journey into early American history.
The site is mostly natural and peaceful, allowing guests to reflect on the history that unfolded here. It’s an excellent opportunity for photography and nature appreciation as well. The surrounding landscapes add to the beauty of the location.
Guided tours may be available, and knowledgeable staff share in-depth stories about the site. Visitors learn about the lives of the tribes and their interactions with early settlers. It’s a great educational experience for families and history enthusiasts alike.
Plan a visit to Fort Corchaug for a unique historical adventure in Southold. The rich history and natural beauty make it a memorable stop.
Address: 19142 Main Rd, Southold, NY 11971.
12. Bike the Seaview Bicycle Route
The Seaview Bicycle Route offers a scenic cycling experience along the North Fork coastline. This route is perfect for cyclists of all skill levels. The beautiful views and fresh air make it a wonderful way to explore Southold.
As you ride, prepare to be amazed by stunning sea views and lush landscapes. The gentle terrain makes for an enjoyable ride, suitable for families and leisurely cyclists. Stop along the way to take in the scenery or grab a snack from local shops.
The route is well-marked, providing clear direction for cyclists. It allows you to discover hidden gems throughout the area, including charming beaches and parks. The chance to experience nature up close enhances the joy of cycling.
Don’t forget to bring your camera! There are many picturesque spots perfect for capturing memorable moments. The surrounding scenery is breathtaking throughout the ride.
Experience the outdoors to the fullest with a bike ride on the Seaview Bicycle Route. It’s an exhilarating way to enjoy Southold’s beautiful landscapes.
Address: Seaview Avenue, Southold, NY 11971.
13. Spend a day at Southold Town Beach
Southold Town Beach is the ideal destination for a relaxing day by the water. With its sandy shoreline and gentle waves, it’s perfect for sunbathing and swimming. The beach provides a welcoming atmosphere for families and friends alike.
You can set up a beach towel, soak up the sun, and enjoy a peaceful day by the water. The calm waves are perfect for children to play in. Bring your beach toys, and make it a fun-filled day of play!
Southold Town Beach also has facilities for picnicking. You can bring your lunch and enjoy a meal with stunning views of the Long Island Sound. There are picnic tables available, making it easy to relax with family and friends.
Fishing is popular in the area, too. Cast your line from the shore and try your luck at catching local fish! It’s a leisurely way to spend your time and connect with nature.
Visit Southold Town Beach to unwind and enjoy a beautiful day by the water. The day’s memories will surely bring you back again!
Address: 2500 S Harbor Rd, Southold, NY 11971.
14. Go fishing at Southold Bay
Southold Bay is a fishermen’s paradise, offering ample opportunities to catch local fish. With its rich marine ecosystem, fishing here is both relaxing and rewarding. Anglers of all experience levels can enjoy a day on the water.
You can fish from shore or rent a boat for a more adventurous outing. The bay’s calm waters make it safe and accessible for both beginners and experienced fishermen. Whether you’re casting from the shore or out on a boat, there’s excitement in every nibble!
Local bait and tackle shops can equip you with everything you need for a successful day. They often provide helpful tips on where to find the best catches. You’ll feel welcomed as part of the fishing community in Southold.
Don’t forget to bring your cooler! It’s always a plus to enjoy some fresh-caught fish after your fishing adventure. Cooking up your catch is a satisfying way to end the day.
Plan a day of fishing at Southold Bay for a fun and tranquil outdoor experience. It’s a great way to connect with nature and enjoy the beautiful surroundings.
Address: 2255 S Harbor Rd, Southold, NY 11971.
15. Explore the Southold Historical Society Museum
The Southold Historical Society Museum is a treasure trove of local history. This museum showcases artifacts and exhibits that narrate the stories of Southold’s past. It’s an engaging experience for visitors of all ages.
As you explore the various exhibits, you’ll learn about the area’s early settlers and Indigenous tribes. The staff is knowledgeable and eager to share insights about the town’s history. It’s a fantastic opportunity to deepen your understanding of Southold.
The museum also hosts events and lectures throughout the year. These gatherings often focus on different aspects of local history, enhancing the community’s cultural enrichment. Participating in these events can be both enjoyable and educational.
Don’t forget to visit the museum shop for unique souvenirs. You can find locally made crafts and historical books to remember your visit. It’s a great way to support local artists and authors.
Make time to visit the Southold Historical Society Museum. It’s an excellent stop for anyone interested in history and culture!
Address: 54325 Main Rd, Southold, NY 11971.
16. Visit the Lavender Farm at Harbes Family Farm
The Lavender Farm at Harbes Family Farm is a delightful experience for nature lovers. The vibrant lavender fields create a colorful and aromatic landscape. You can soak in the beauty while the sweet fragrance surrounds you.
During peak season, the farm opens its fields to visitors for U-Pick lavender. It’s a fun activity to gather fresh lavender for your home or as a special gift. The farm staff provides tips on how to harvest carefully.
The farm features a charming shop where you can purchase lavender products. From essential oils to sachets, there are many ways to bring home the essence of lavender. Each product highlights the farm’s commitment to quality and sustainability.
The farm often hosts events, which include family-friendly activities, live music, and more during harvesting seasons. It’s a lively place that brings community members together throughout the year.
Plan a visit to the Lavender Farm for a relaxing and fragrant outing. The beauty and tranquility will leave you feeling rejuvenated.
Address: 715 Sound Ave, Mattituck, NY 11952.
17. Attend a wine tasting at Macari Vineyards
Macari Vineyards is a delightful destination for wine lovers. The vineyard offers wine tastings amid beautiful views of the North Fork. With a variety of wines to sample, guests can experience the richness of local winemaking.
During the tasting, knowledgeable staff explain the characteristics of each wine. They guide you through each sip, pointing out unique flavors and aromas. It’s an enjoyable education in wine appreciation!
The scenic location adds to the experience. You can sip your wine on their terrace, surrounded by picturesque vineyard landscapes. It’s the perfect setting for a leisurely afternoon.
Macari Vineyards also offers food pairings, enhancing the tasting experience further. Enjoy freshly made bites that complement the wines and elevate the flavors. It’s a fantastic way to indulge your palate.
Don’t miss out on a wine tasting at Macari Vineyards during your visit. It’s a wonderful way to experience the heart of Southold’s wine culture.
Address: 150 Bergen Ave, Mattituck, NY 11952.
18. Stroll through the gardens at the Southold Historical Garden
The Southold Historical Garden is a peaceful retreat in town. It’s a delightful space where visitors can wander through beautifully designed gardens. Each section showcases different plants and flowers, offering a burst of color throughout the seasons.
As you stroll, take note of the diverse flora that represents local gardening practices. Informative signage provides insights into the plants and their historical significance. It’s an educational experience that enhances your appreciation of regional horticulture.
The garden’s serene atmosphere makes it perfect for relaxation. Bring a book or enjoy a quiet picnic in this tranquil setting. It’s a lovely way to rejuvenate and connect with nature.
Throughout the year, the garden often hosts events and workshops focused on gardening and sustainability. These activities foster community engagement and teach valuable skills.
Don’t miss the chance to visit the Southold Historical Garden. It’s a beautiful space that enriches your Southold experience.
Address: 54325 Main Rd, Southold, NY 11971.
19. Experience local arts at the Southold Arts Council
The Southold Arts Council is the heart of the local arts scene. This organization promotes creative expression through various exhibitions and events. Visiting the council will give you an insight into the vibrant culture of Southold.
Throughout the year, the council showcases works from local artists. The rotating exhibitions provide a fresh perspective on creativity and talent. It’s fascinating to see how local culture inspires artistic expression.
The council also hosts community events like concerts, workshops, and art fairs. You can participate in hands-on activities, meet local artists, and enjoy live performances. These events foster connections among art enthusiasts.
Moreover, the Arts Council emphasizes the importance of arts education. Engage in educational programs designed for all ages. They focus on enhancing skills and nurturing creativity in the community.
Make a stop at the Southold Arts Council during your visit. It’s a wonderful opportunity to immerse yourself in the local arts community.
Address: 53955 Main Rd, Southold, NY 11971.
20. Kayak on the Peconic Bay
Kayaking on the Peconic Bay is an exciting way to explore Southold’s waterways. This adventure allows you to connect with nature and admire the stunning coastal scenery. Rent a kayak or join a guided tour to experience the beauty of the bay.
Paddle your way through calm waters, taking in views of lush landscapes and wildlife. Keep your eyes peeled for various bird species and aquatic life that thrive in the bay. The tranquility of the water enhances your experience.
Kayaking is suitable for beginners and experienced paddlers. The calm waters of Peconic Bay make it accessible for everyone. Enjoy the freedom to explore at your own pace and discover hidden gems along the shoreline.
You can also bring a picnic to enjoy on one of the secluded beaches you find along the way. It’s a delightful way to relax after a day of kayaking.
Plan a kayaking adventure on Peconic Bay during your visit. It’s an unforgettable way to enjoy Southold’s natural beauty.
Address: Peconic Bay, Southold, NY 11971.
21. Relax at Founders’ Landing Park
Founders’ Landing Park is a serene retreat on the waterfront. This park provides stunning views of the Long Island Sound, making it a perfect spot for relaxation. You can enjoy a leisurely stroll or find a bench to take in the peaceful surroundings.
The park features picnic areas, allowing families to gather and enjoy a meal outdoors. Bring a picnic basket to enjoy lunch while watching the boats go by. The inviting atmosphere makes it easy to unwind.
Fishing is another popular activity at Founders’ Landing Park. The accessible shoreline provides opportunities to catch local fish. Spend the day enjoying the tranquility of the water while casting your line.
In addition, the park is well-maintained, with walking paths and green spaces to explore. It’s an excellent space for kids to play and for families to bond. The surrounding nature enhances the beauty of your visit.
Visit Founders’ Landing Park for a relaxing day by the water. It’s the perfect way to enjoy Southold’s natural beauty.
Address: 800 N Main St, Southold, NY 11971.
22. Discover the local farmers’ market
The Southold Farmers’ Market is a vibrant hub of local produce and creativity. This market offers a variety of fresh fruits, vegetables, and handmade goods from local vendors. It’s a delightful place to connect with the community and support local agriculture.
As you stroll through the market, you’ll find seasonal products reflecting the region’s agricultural bounty. Pick up fresh organic produce, baked goods, and artisanal products. Each vendor adds unique flavors to the market, making it an enjoyable shopping experience.
In addition to food, the market often features crafts and artwork from local artisans. It’s great for finding unique, handmade gifts that support the community. The creativity and craftsmanship displayed enhance the market’s charm.
The market is also a social gathering place. Enjoy the lively atmosphere and interact with local farmers and producers. You might even catch live music or special events happening during your visit.
Don’t miss the chance to explore the Southold Farmers’ Market. It’s a fantastic way to experience the local culture and flavors.
Address: 54005 Main Rd, Southold, NY 11971.
23. Take a scenic drive along North Fork Wine Trail
The North Fork Wine Trail offers a picturesque drive through beautiful vineyards and charming towns. This scenic route is perfect for a day of exploration. As you drive, enjoy breathtaking views of the countryside and the sparkling waters of the Sound.
Along the way, you can visit various wineries, each offering unique wines and ambiance. Many wineries have outdoor seating and tasting rooms, allowing you to savor your selections amid stunning landscapes. Don’t hesitate to stop at multiple locations to fully experience what the North Fork has to offer!
In addition to wineries, you’ll discover artisanal shops, local restaurants, and fresh produce stands as you travel. The vibrant community is rich with flavors and experiences waiting to be explored. A stop for lunch at a local eatery is highly recommended.
The drive is especially beautiful during the harvest season, with vibrant autumn colors adding to the scenery. Each winery has its own charm, promising delightful tastings and fun interactions.
Make a day of it and hit the North Fork Wine Trail for an unforgettable ride through stunning landscapes and delicious wines.
Address: North Fork Wine Trail, Southold, NY 11971.
24. Visit the Southold Fish Market
The Southold Fish Market is a must-visit for seafood lovers. Known for its fresh catch, the market offers a wide variety of seafood options. From fish fillets to crabs and shrimp, you’ll discover delightful tastes at this local gem.
The friendly staff provides excellent service, helping you select the freshest seafood for your meal. Whether you need a special ingredient for a recipe or simply want to cook up some shrimp for dinner, they have you covered.
Many locals rave about the market’s quality, as it sources fish from local waters. You can trust that you’re getting delicious seafood that supports the community. Visit the market for a taste of the local flavor!
In addition to seafood, the market often features prepared dishes, making it easy to grab a meal on the go. Some favorites include clam chowder and fish tacos. Pair your meal with local wine for a perfect dining experience.
Don’t miss the Southold Fish Market during your visit. It’s the perfect stop for delicious and fresh seafood.
Address: 55975 Main Rd, Southold, NY 11971.
25. Go antiquing in Mattituck
Antiquing in Mattituck is a delightful experience for treasure hunters. This charming town is home to several antique shops filled with unique finds. You can spend hours browsing through vintage items and collectibles that tell their own stories.
Each shop has its own character and offers various antiques, from furniture to jewelry. Many shops pride themselves on curating a diverse selection of items with rich histories. It’s a great way to connect with the past while finding something special.
Don’t hesitate to ask shop owners about particular items; they are often very knowledgeable and passionate about what they sell. You may discover unexpected stories and hidden gems as you explore.
Mattituck also has quaint eateries nearby, making it a perfect day trip destination. After a successful morning of antiquing, enjoy lunch or coffee to recharge before continuing your adventure.
Plan a visit to the antique shops in Mattituck for an enjoyable day of exploration. It’s a treasure trove waiting to be discovered!
Address: Mattituck, NY 11952.
Final Thoughts
Southold, NY, is a charming destination brimming with diverse attractions and experiences. Whether you’re savoring award-winning wines, exploring local history, or enjoying nature’s beauty, there’s something for everyone. The warm community and stunning surroundings create a welcoming atmosphere that enriches every visit.
As you leave, the memories of beautiful vineyards, tranquil beaches, and charming markets will draw you back to Southold again and again. If you’re looking to expand your travels, consider exploring other incredible places to visit in New York, or venture north to see the captivating scenery in Upstate New York. Plan your trip to uncover the treasures of this captivating coastal town!