Guidebook for Southold
Food Scene
Some of the best fine dining on the East End! For a more casual experience try their bar menu in the evenings. Also their food truck (open 11a-3p) is a must visit. It's a great place to grab lunch from when sitting on the beach all day!
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North Fork Table & Inn
57225 Main RdSome of the best fine dining on the East End! For a more casual experience try their bar menu in the evenings. Also their food truck (open 11a-3p) is a must visit. It's a great place to grab lunch from when sitting on the beach all day!
North Fork Roasting Co.
55795 Main RdIf you need your coffee fix!
Grateful Lee Deli
55700 NY-25Great deli sandwiches for a day at beach!
Lucharitos
119 Main StFun vibe, good Mexican food and great cocktails!
Nice outdoor seating. Family (and allergy) friendly, Greek food. Don't miss Hellenic's Hard Lemonade!
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Hellenic Snack Bar & Restaurant
5145 Main RdNice outdoor seating. Family (and allergy) friendly, Greek food. Don't miss Hellenic's Hard Lemonade!
1943 Pizza Bar
Main StreetPizza!
A cute general store, operated by two former Brooklynites. They make amazing breakfast and lunch sandwiches. Don't miss the BLT and the Fried Chicken sandwiches! And if they have soft serve machine going, get some!
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Fork & Anchor
8955 Main RdA cute general store, operated by two former Brooklynites. They make amazing breakfast and lunch sandwiches. Don't miss the BLT and the Fried Chicken sandwiches! And if they have soft serve machine going, get some!
The Frisky Oyster
27 Front StAmerican Beech
300 Main StDrinks & Nightlife
Some of the best cocktails on the East End! You can order food here too, which shares a kitchen and menu with the 1943 Pizza Bar upstairs. Don't miss the Burrata with fire roasted tomatoes!
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Brix & Rye
308A Main StSome of the best cocktails on the East End! You can order food here too, which shares a kitchen and menu with the 1943 Pizza Bar upstairs. Don't miss the Burrata with fire roasted tomatoes!
Wine bar for our favorite vineyard. A nice place to hang out and enjoy a bottle of wine with seating both inside and in their covered backyard. (Their vineyard location is beautiful, but is now members only.) In addition to selling Roanoke wine, you can also often find Wölffer, Red Hook and Channing Daughters wine here - all of which are stellar!
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Roanoke Vineyards Wine Bar
165 Love LnWine bar for our favorite vineyard. A nice place to hang out and enjoy a bottle of wine with seating both inside and in their covered backyard. (Their vineyard location is beautiful, but is now members only.) In addition to selling Roanoke wine, you can also often find Wölffer, Red Hook and Channing Daughters wine here - all of which are stellar!
Shinn Estate Vineyards and Farmhouse
2000 Oregon RdSmall family business, on an amazing property, with chickens running free. Don't miss the Commodore Perry Merlot!
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The Old Field Vineyards
59600 NY-25Small family business, on an amazing property, with chickens running free. Don't miss the Commodore Perry Merlot!
Croteaux Vineyards
1450 S Harbor RdOne Woman Wines & Vineyards
5195 Old North RdNewly renovated restaurant with amazing views. A great place to have a cocktail and watch the sunset. Classic piano bar often has live music and piano sing-a-longs, if you get lucky.
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The Halyard Restaurant
58775 County Rd 48Newly renovated restaurant with amazing views. A great place to have a cocktail and watch the sunset. Classic piano bar often has live music and piano sing-a-longs, if you get lucky.
Essentials
Southold IGA
54560 NY-25Great local grocery store that often features local produce.
Southold Pharmacy
53895 NY-257-Eleven
56480 Main RdOpen 24 hrs!!!
Entertainment & Activities
Drossos Motel
69125 Main RdMini Golf!!!
Peconic Water Sports
64150 Main RoadRent anything you might need to have fun on the water!
Fascinating look at how oysters are cultivated, including a tour of the oyster hatchery and a tasting of their oysters paired with local wines. A great way to spend a couple hours!
Southold Bay Oysters
10273 N Bayview RdFascinating look at how oysters are cultivated, including a tour of the oyster hatchery and a tasting of their oysters paired with local wines. A great way to spend a couple hours!
Getting Around
Southold station
Long Island Railroad (LIRR) Southold station.
John F. Kennedy International Airport
Nearest international airport.
Parks & Nature
Kid friendly beach down the street from us with lifeguards (in summer), swings, slides, etc...
Founders Landing Park
1025 Terry LnKid friendly beach down the street from us with lifeguards (in summer), swings, slides, etc...
Town Harbor Lane
Town Harbor LanePrivate beach at the end of the road.
Arts & Culture
Southold Historical Society
54325 NY-25