Overview
Southold is a town in Suffolk County, New York. It is the eastern half of Long Island's North Fork.
6 things to do · 17 places to eat · 24 bars & cafés
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Southold
Greenport Skatepark, Ice Skate Rink & Carousel
Strong's Marine, LLC
This place allows for renting boats and does provide boating lessons.
Harbes Family Farm
Allows you to pick your own fruit and vegetables as well as flowers. It is open from May till October. The months depend on what you are able to pick.
Sannino Vineyard B&B
An exclusive Tuscan Suite on a private vineyard Private entrance and balcony overlooking the vineyard King Size bed, 700 sq. feet of luxury Breakfast in Bed
Orient Beach State Park
Small waterfront Park known for its pristine views of Long Island Sound and ample fishing.
Horton Point Lighthouse Nautical Museum
Local history museum housed in an 1857 lighthouse.
Plan your trip
Best time to visit & weather
Most comfortable: May–Oct. Summer highs reach about 83°F; winter lows dip to about 15°F. Cold months (Jan, Feb) can bring snow and ice; check road conditions. Wettest: Oct and Aug. (climate data from nearby Waterbury)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- HVN Tweed New Haven Airport, New Haven — 27 mi away. Directions
- WST Westerly State Airport, Westerly — 38 mi away. Directions
- BDL Bradley International Airport, Hartford — 62 mi away (major hub). Directions
The Long Island Rail Road offers service on the Main Line - Greenport Branch.
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Sample 2-day itinerary
Day 1
- Morning Greenport Skatepark, Ice Skate Rink & Carousel, Harbes Family Farm
- Lunch A Touch of Venice
- Afternoon Orient Beach State Park
- Dinner Braun Seafood
- Evening Ackerly Ponds
Day 2
- Morning Strong's Marine, LLC, Sannino Vineyard B&B
- Lunch Claudio's Clam Bar & Wharf
- Afternoon Horton Point Lighthouse Nautical Museum
- Dinner Claudio's Crabby Jerry's
- Evening Bedell Cellars
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Map
Every listing with a location. Tap a pin for its Google Maps link.
Understand
The town of Southold covers most of the "North Fork" or northeastern peninsula of Long Island. It is more rural in character than most parts of Long Island and is well known for its wineries, farms, and fishing towns. The town's main settlement is the village of Greenport, but it also contains the hamlets of Cutchogue, East Marion, Fishers Island, Laurel, Mattituck, New Suffolk, Orient, Peconic, and Southold.
Get in
By train
The Long Island Rail Road offers service on the Main Line - Greenport Branch.
By car
By ferry
The Cross Sound Ferry offers service from New London, Connecticut to Orient.
Go Orient Point Ferry Terminal
Do
Although there are a few wineries on the South Fork of Long Island, the Hamptons, the vast majority are located on the North Fork of Long Island.
The North Fork of Long Island has many beaches as well as park trails. As well as these beaches and park trails, the North Fork of Long Island is known for their many wineries as well as a small knit community.
Eat
Drink
The entire town is included within the North Fork of Long Island American Viticultural Area and is a popular destination for wine tourism.
Drink Duck Walk North Vineyard
Drink Macari Vineyards and Winery
Drink Sannino's Bella Vita Vineyard, LLC
Drink Sherwood House Vineyards
Go next
Nearby
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City / town · 27 listings · 4 mi away
Sag Harbor
City / town · 2 listings · 9 mi away
Southampton
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East Hampton
City / town · 8 listings · 14 mi away
Riverhead
City / town · 21 listings · 15 mi away
Old Saybrook
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Clinton
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Old Lyme
City / town · 21 listings · 19 mi away
My experience
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