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We've compiled the best of the best in Southold - browse our top choices for the top things to see or do during your stay.
A short, winding road leads to this airy, chaletlike tasting house with a spacious deck and one of the best vineyard views in the area. They host events like the Twilight Series, featuring live music and food trucks from late May to early September, some for an additional cover charge. Now under the banner of Bedell Cellars, they continue to produce acclaimed wines like the Chardonnay Reserve and Late-Harvest Reisling.
Taking advantage of some of the darkest night skies on Long Island, this observatory is a prime viewing spot for astronomy buffs and star-deprived urbanites. Atop the barnlike structure is a motorized dome with a telescope you can use to track the heavenly view. Clear skies are the best for observing; avoid coming during a full or almost-full moon.
The 58-foot-tall lighthouse, operated by the Southold Historical Society, was built in 1847. Together with the adjoining lighthouse keeper's home, it resembles a church. The museum, in the keeper's residence, displays sea captains' journals, sea chests, paintings, and maps. Enjoy the 8-acre park surrounding the lighthouse.
Christian and Rosamund Baiz's family homestead is the setting for this small winery with a rustic farm setting, right down to the chickens and dog roaming the property. Operations are sustainable and organic whenever possible, and the wines are made by one of the area's top winemakers. The Cracklin' Rosé is a fun choice with flavors of orange blossom, white cherry, and cranberry. Tastings are in an small, old barn or picnic-style by the beach. Historical and agricultural tours are among the events held here.
The complex, run by the Southold Historical Society, encompasses a dozen buildings, several of which are listed on the New York State Register of Historic Places. Arranged as a quaint village, they include the home of the society's founder, Ann Currie-Bell, with antique dolls and toys, costume collections, and period rooms; the Thomas Moore House, a mid-18th-century carriage house and blacksmith shop; the circa 1821 Old Bay View School, which now looks as it did in 1914; and a buttery and icehouse.
