Southold Vineyard Tour

Southold, New York 11971

Southold Vineyard Tour

Southold Vineyard Tour Professional Guide

Detailed Trail Description from our Guidebook

"Southold was known to the local Shinnecock tribes as Yennicott before English settlers arrived from the New Haven Colony in 1640. The region might have stayed part of Connecticut if not for the intervention of James, Duke of York, who demanded they be governed by the Province of New York.

This ride maps out three of the top vineyards in Southold, but many more are easily accessible off and on the route: Check the full list of vineyards in the Ride Information section below. Starting at the Southold station on Traveler Street, the route immediately turns right, onto Youngs Avenue, past a town green and across NY 25. Youngs Avenue flows downhill over the next quarter-mile, curving left along the Town Creek and becoming Calves Neck Road."

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Trail Information

Nearby City
Trail Type
Skill Level
40-60 minutes
Riding Time

Trail Log