Go oyster shucking and learn all about the history of Long Island oysters! It's an experience unique to Long Island's North Fork and you'll get to meet the farmers and fishermen (and history: The house at Widow's Hole is 200 years old and was owned by the Chrysties—John Chrystie was a hero of the War of 1812) behind some of the most delicious oysters you'll ever have.
Removed from the oft-maddening traffic along the Wine Trail (and conveniently located close to the wedding venue), Kontokosta is the North Fork’s most sophisticated vineyard and is in a league of its own. Exclusive with a dramatic waterfront setting overlooking the bluffs of Long Island, Kontokosta is all about sustainability in the production of sauvignon blanc, viognier, riesling, merlot, and cabernet.
One Woman's Winery taproom offers a special chance to taste the fruit of Claudia Purita's hard work. This one-woman show, specifically a farm and vineyard in Southold, offers flights for $25 (regular: Grüner Veltliner, Sauvignon Blanc, Chardonnay, Merlot) and $30 (reserve: Reserve Chardonnay, Roccia - a Bordeaux style blend, 2013 Reserve Merlot, and Dessert Grüner Veltliner) as well as wines by the glass and bottles.
Greenport Harbor Brewing tasting room is located in an old firehouse, is the best place for casual drinks with friends. At $8 per tasting/flight, it's easy to find a favorite brew (you've likely had their product before if you've been around New York for a time), whether its the Otherside IPA, Harbor Ale, Black Duck Porter or any of its imaginative limited edition brews, including its Chocolate Covered Cherry Pie stout.
Head over to the East End Seaport Museum in the former station house of the LIRR to learn the area's rich and long history and ride the antique 1920s carousel near the waterfront!