Things To Do
in Southold
Southold is a picturesque town on the North Fork of Long Island, celebrated for its maritime heritage, rolling farmland, and scenic vineyard corridors. It anchors a string of villages along the Peconic Bay, offering harbor views, farm stands, and seafood-centric dining. The region blends rural charm with coastal character, making it ideal for relaxed day trips and slow, scenic weekends.
From historic lighthouses to family-owned wineries, Southold invites exploration, cuisine, and outdoor enjoyment with a distinctly North Fork flavor.
Day Trips
Spend a day exploring around
Start your day with a visit to the Southold Historical Society, where you can delve into the rich maritime history of the area. Enjoy a leisurely stroll through the charming streets of the historic district, taking in the colonial architecture and local boutiques. Don’t forget to grab a fresh pastry at a local café to fuel your exploration.
After lunch at a cozy bistro, head to the Southold Town Beach for some relaxation and stunning ocean views. Engage in some beachcombing or simply lay back and soak up the sun while listening to the gentle waves. As the afternoon progresses, consider renting a kayak to explore the nearby marshes and waterways.
As the sun begins to set, make your way to a waterfront restaurant for a delicious seafood dinner with a view. Savor the local flavors of Long Island, perhaps sampling fresh clams or a lobster roll. End your evening with a peaceful walk along the beach, watching the stars emerge in the clear night sky.
Kick off your day with a hearty breakfast at a local diner known for its delicious pancakes and fresh coffee. Afterwards, set out on a scenic drive through the North Fork Wine Country, where vineyards stretch as far as the eye can see. The morning is perfect for visiting a couple of local wineries for tastings and tours.
Continue your wine adventure with a picnic lunch at one of the vineyards, surrounded by lush grapevines. After lunch, take part in guided tours that often include insights into the wine-making process and the chance to sample unique blends. Enjoy the relaxed atmosphere as you sip on a glass of wine while taking in the picturesque landscape.
As the day winds down, visit a winery that offers sunset tastings on their patio. Bask in the warm glow of the setting sun while enjoying a flight of wines paired with artisanal cheeses. Wrap up the evening with a seasonal dessert and perhaps a nightcap before heading back to your accommodations.
Prices
| Item | Price |
|---|---|
| 🍔Meal at inexpensive restaurant | $10-15 |
| 🥗Lunch at mid-range restaurant | $15-25 |
| 🛏️Hotel or inn per night | $150-250 |
| 🚗Gasoline per gallon | $4-5 |
| 💊Over-the-counter essentials | $5-20 |
Strengths and Weaknesses
- Scenic coastlines and a relaxed pace
- Strong farm-to-table and wine scene
- Limited public transit outside major hubs
- Seasonal crowds can peak in summer
Places to Visit in Southold
Visit one of these nice places.
Morning light on colorful boats and the harbor promenade makes for soft reflections and pastel skies.
Dramatic coastal cliffs and a historic lighthouse with expansive Sound views, ideal for wide-angle ocean shots.
Coastal bluff lines, sweeping ocean views, and seabird activities—perfect for silhouettes at sunset.
Rows of vines and pastoral farmland provide gentle backdrops and warm light during golden hour.
Quaint farmstands, boats, and bay views offer candid opportunities for rustic, regional photography.
Food in Southold
Southold Famous Food
Signature dishes, delicacies and famous food
Succulent lobster meat on a buttered or mayo-dressed roll; widely served at docks and seafood shacks in Greenport and Mattituck.
Must-Try!
Fresh, locally farmed oysters from Peconic Bay; try at harborfront eateries or Little Creek Oyster Farm & Market.
Sun-ripened corn from North Fork fields, a summer staple found at farm stands and farmers markets.
Creamy, hearty chowder featuring locally caught clams, available at coastal cafes and seaside shacks.
Food Markets
Explore local food markets
Seasonal market with local produce, seafood, baked goods, and prepared foods near the harbor area.
Weekly market offering fresh produce, meats, dairy, and ready-to-eat treats from North Fork farms.
Small-town market with vegetables, fruit, jams, and local specialties in the heart of the village.
Weather
How to Behave
Tips on cultural norms and respectful behavior
Greet staff with a friendly 'Hello' or 'Good day.' Tipping is customary; speak politely, and maintain a moderate voice in shops and restaurants. Respect private property and farm gates, and ask before taking photos of people or harvests.
Safety
Tipping in Southold
Ensure a smooth experience
Restaurants typically expect 15-20% gratuity; for bars 10-15%. Tip hotel staff and tour guides similarly, and consider small amounts for exceptional service.
Credit/debit cards are widely accepted; cash is still handy at farmers markets and small eateries. Contactless payments are common, and ATMs are readily available.
Best Time to Visit
And what to expect in different seasons...
Peak beach season with warm days and breezes off the Sound. Expect crowds near popular harbors and wineries; book tastings and ferries in advance.
Harvest time with cooler days, changing leaves, and wine-tasting events. Ideal for outdoor photography and scenic drives through vineyards.
Quieter streets and fewer open restaurants; cozy winery tasting rooms and indoor dining offer a calm escape with fewer crowds.
Blossoming orchards and fresh market produce return. Pleasant for biking and walking, with gradually warming temperatures.
Southold at Night
Hiking in Southold
Immerse in an unforgettable hike.
Coastal woodlands and tidal marsh trails offering birding, quiet shoreline walks, and sea views.
Coastal bluff walk with panoramic Sound views and a chance to photograph the lighthouse area.
Cliffside paths and shoreline routes ideal for sunset photography and scenic coastal hiking.
Airports
How to reach Southold by plane.
Nearest major regional airport offering domestic flights; about 60-70 miles west via route and highway connections.
Regional airport to the north, offering limited domestic services; useful for certain connections and short trips.
Major international hub farther east; offers extensive flight options and connections to many destinations.
Walkability
Demographics
Explore demographics in this area.
Many families visit for beaches, farm stands, and kid-friendly farm experiences.
Vineyard tours, tastings, and farm-to-table dining draw visitors who appreciate regional cuisine.
Quieter off-season periods and scenic landscapes attract seasonal residents and long-term visitors.
Popular Sports
Explore popular sports in region.
Harness the coastal winds and bay waters with chartered sails or local clubs along the Sound.
Coastal and inshore fishing opportunities abound, with charters and local markets providing gear and tips.
Several scenic courses on the North Fork offer rolling greens and water features.
Traffic
Accomodations
Find the best place to stay when visiting Southold.
Dietary Restrictions
Tips for restricted diets.
North Fork menus emphasize vegetables, grains, and dairy; look for seasonal veg dishes, salads, and plant-based options. When dining out, ask for vegetable-forward plates, dairy-free preparations, or meatless substitutes; many markets offer fresh produce you can prep yourself.