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The Old Field Vineyards in Southold. (Credit: Charity Robey)

The Old Field Vineyard with Southold Bay shimmering at the edge of the vineyard. Charity Robey

I like wine, and I like visiting farms.

But I’ve never taken a tour of North Fork Wine Country, even though I’ve admired the landscape and the wines for years.

So I decided to explore both the farmland and the wines this spring — by bicycle.

I mapped two routes with scenery and serenity in mind. Each one amounts to about an hour of easy pedaling and is dead flat. Cyclocross, this was not. No carbon frames, spandex shorts or aerodynamic accessories are required.

Both routes take in small, low-key wineries situated in the earthy farm paradise we call the North Fork.

The Mattituck/Oregon Road Bike Loop
The Mattituck/Oregon Road Bike Loop


Editor’s Note: The Sherwood House tasting barn is no longer located along this route. The tasting room can be found at 1291 Main Road in Jamesport.

Oregon Road just might be the most beautiful country road anywhere, and this 8.5-mile route makes the most of it.

Starting at the train station, I pedal through town on Pike and Wickham, and across Route 48, where the stoplight comes in handy. Next is a lovely stretch of Wickham Avenue and Mill Road, with beautiful old homes and tiny Wolf Pit Lake. A right onto Oregon Road puts me in the heart of prime North Fork farmland. Acres of fields and farmhouses spread out around me as I arrive at Shinn Estate Vineyards. (See map above for the full loop)

You will hit Shinn Estate Vineyard, Lieb Cellars and Castello di Borghese.

The Southold Bike Loop
The Southold Town and Country Bike Loop


The route is about 12 miles. It begins and ends at the Southold train station, and features three small vineyards, each with a distinct personality.

The ride is an easy and beautiful loop that takes in the charm of Southold, as well as the farms and waterways that lace the area.

From the station I head east on Traveler Street and turn south to cross Main Street at the light. Passing Town Creek and into Calves Neck, the road turns and winds along the water. I cross Jockey Creek with more winding and turning until I see the rows of grapevines that indicate my goal is nigh. (See map above).

You will hit Croteaux Vineyards, Southold Farm + CellarThe Old Field Vineyards and One Woman Wines and Vineyards.

This story was original published in the summer 2014 edition of northforker’s Long Island Wine Press.