Guidebook for Southold
Everything Else
Great little vineyard - just a few minutes on a bike. Enjoy their award-winning chardonnay or bright rosé outside on a picnic table. Sip wine while listening to live music, overlooking the vineyards.
5195 Old North Rd
5195 Old North RoadGreat little vineyard - just a few minutes on a bike. Enjoy their award-winning chardonnay or bright rosé outside on a picnic table. Sip wine while listening to live music, overlooking the vineyards.
Macari Vineyards & Winery
24385 Main RdTry the Bergen Road...
39750 County Rd 48
39750 County Road 48The one and only vineyard on the North Fork that specializes in Sparkling wine.
The BEST pie around. Try the Raspberry Cream. Also enjoy a nice selection of fresh fruits, vegetables and flowers.
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Briermere Farms
4414 Sound AveThe BEST pie around. Try the Raspberry Cream. Also enjoy a nice selection of fresh fruits, vegetables and flowers.
Food Scene
One of the top-rated restaurants in New York State (including NYC). Enjoy their tasting menu accompanied by a beautiful selection of wine.
Main Road
Main RoadOne of the top-rated restaurants in New York State (including NYC). Enjoy their tasting menu accompanied by a beautiful selection of wine.
Good food, all around. Breakfast, lunch or dinner.
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Hellenic Snack Bar & Restaurant
5145 Main RdGood food, all around. Breakfast, lunch or dinner.
Love, love, love their filet mignon sliders. And duck tacos. Great spot for dinner.
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Noah's
136 Front StLove, love, love their filet mignon sliders. And duck tacos. Great spot for dinner.
If you're looking for a dark, local pub to grab a pint, this is your place. It's a quick drive or about a fifteen minute bike ride away from the house.
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Founders Tavern
55500 NY-25If you're looking for a dark, local pub to grab a pint, this is your place. It's a quick drive or about a fifteen minute bike ride away from the house.
Open late every night - they have the largest selection of burgers in the area. Kitschy and spectacular, it's one of my faves. (Don't stray too far from the burgers, although the Prime Rib is ok)
O'Mallys
44780 Rte 48Open late every night - they have the largest selection of burgers in the area. Kitschy and spectacular, it's one of my faves. (Don't stray too far from the burgers, although the Prime Rib is ok)
One of the original 'nice' restaurants in Greenport. During summer you can eat outside on the dock.
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Scrimshaw
102 Main StOne of the original 'nice' restaurants in Greenport. During summer you can eat outside on the dock.
Bonnie Jean's Casual American Eatery
55765 NY-25Decent diner; quick place for breakfast.
A nice restaurant for dinner. Attractive, cozy interior and delicious food. Plus, a trip over to Shelter Island is always enjoyable.
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Vine Street Café
41 S Ferry RdA nice restaurant for dinner. Attractive, cozy interior and delicious food. Plus, a trip over to Shelter Island is always enjoyable.
Sightseeing
Commissioned by George Washington, this lighthouse is not only historic but has amazing views. Bike here, take a tour, bring a picnic, enjoy the grounds - all while overlooking the sound.
3575 Lighthouse Rd
3575 Lighthouse RoadCommissioned by George Washington, this lighthouse is not only historic but has amazing views. Bike here, take a tour, bring a picnic, enjoy the grounds - all while overlooking the sound.
Dam Pond
There are excellent views and a fun, flat hike at Dam Pond.
Southold Beach Motel
53250 North RoadTown beach is a four minute walk from the house.
Railroad Museum of Long Island
440 4th StA cute little museum.
Front Street
Front StreetA beautiful and enclosed carousel overlooks the harbor in Greenport.
Founders Landing Park
1025 Terry LnA nice park and beach - great for the family.
Bailie Beach Park
1901 Bailie Beach RdAnother beach area, on the Sound
An amazing park at the end of Long Island. A great play ground for kids, spectacular views, nice hiking.
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Orient Beach State Park
40000 Main RdAn amazing park at the end of Long Island. A great play ground for kids, spectacular views, nice hiking.
Shopping
On a rainy day hit the outlets. You'll find Barneys, Off Fifth, J Crew, Nike, Gap, West Elm, Williams Sonoma, Pottery Barn, Ralph Lauren among many others.
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Tanger Outlets Riverhead
1770 W Main StOn a rainy day hit the outlets. You'll find Barneys, Off Fifth, J Crew, Nike, Gap, West Elm, Williams Sonoma, Pottery Barn, Ralph Lauren among many others.
If you need an outfit to wear to the beach, near the beach, on a yacht, or even if you just want to LOOK like you're heading to a yacht, this is your place. Beautiful clothing + beach cover ups, etc.
Calypso St. Barth
15 Front StIf you need an outfit to wear to the beach, near the beach, on a yacht, or even if you just want to LOOK like you're heading to a yacht, this is your place. Beautiful clothing + beach cover ups, etc.
Essentials
Amazing selection of seafood. Delicious, fresh clams. You can eat here, as well...
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Braun Seafood Co.
30840 Main RdAmazing selection of seafood. Delicious, fresh clams. You can eat here, as well...
Wayside Market
55575 NY-25Excellent cuts of meat. Fresh, homemade mozarella.
Amazing selection of cheeses. Try the Humbolt Fog. Get some quince. Pick up a few crackers. And bring it with you on a tour of the vineyards.
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The Village Cheese Shop & Café
105 Love LnAmazing selection of cheeses. Try the Humbolt Fog. Get some quince. Pick up a few crackers. And bring it with you on a tour of the vineyards.
Our nearest grocery store... It has good produce, a decent deli, and every mustard imaginable. although all along the roads you'll find fresh vegetable and fruit stands...
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Southold IGA
54560 NY-25Our nearest grocery store... It has good produce, a decent deli, and every mustard imaginable. although all along the roads you'll find fresh vegetable and fruit stands...