When I think of all-American towns, it doesn’t get more American than the town of Southold, founded in 1640 by Puritans from the New Haven Colony.
Although Southold is in New York State, it has a New England feel to go along with it’s agricultural and maritime economy. According to Antonia Booth, a renowned Southold historian, “Southold’s official flag proclaims it the oldest English town in New York State”. If you want to learn more about local history, visit the Southold Town Historical Society on Route 25, near the Country Corner Cafe and the Wayside Deli where you can get great cuts of meat and even veal bone for your stocks.
Discover Southold on foot and stop at one of my personal favorites, Complement the Chef , a shop that is any cook’s dream with a great selection of pots, pans, grilling gadgets, baking supplies and more.
Southold is home to one of New York’s premier restaurants, North Fork Table and Inn, the perfect spot to celebrate a special occassion. For those nights when you want to relax over some pub fare and an ice cold beer, head to Founder’s Tavern or the Piping Plover Cafe in the Featherhill Mall for fresh salads and delicious sandwiches along with plenty of other shopping.
Southold is home to several vineyards including Corey Creek, Duckwalk, Old Field, Sparkling Pointe and more. These tastings rooms all have their own personality and some of them have giftshops and entertainment. On summer nights you can check out Moonlight Mondays and Twilight Tuesdays with live music and pizza to accompany your wine tastings at Corey Creek Vineyards from 5 to 9 p.m. The Old Field Vineyard has a monopoly on the majestic backdrop of the vines against the still waters of the Peconic Bay. Duckwalk Vineyards has a grand tasting room where you’ll find a great time year round — rain or shine (and you cannot leave without a bottle of their Blueberry Port).
For other Southold shops and historic sites please visit the links below.