Chillin’ on the Choptank

Chillin’ on the Choptank 2017-04-29T15:45:48+00:00

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The inaugural Chillin’ on the Choptank outdoor festival will be held at Sailwinds Park in Cambridge, Maryland, on Friday evening and Saturday of Memorial Day weekend. The two-day event features wine and beer tastings, local oysters and other regional fare, and live music — all overlooking the Choptank River. Sailwinds is at 200 Byrn St., Cambridge, Maryland.

Friday, May 26, kicks off with a Small Plates Pairing Dinner featuring food by Chef Henry of Tilghman Island’s Two If By Sea Restaurant from 7 to 10pm. The sit-down, five-course, small plate dinner will be served riverside, with expertly paired wine, beer, and spirits. A jazz concert under the stars will cap the evening. A jazz concert by vocalist Scotti Preston immediately follows dinner. NOTE: Seating is limited, and ticket sales for the diner close May 12!

On Saturday, May 27, the Wine, Beer and Oysters Tasting kicks off at 12pm, featuring more than 200 wines from California, Italy, France, Germany, Chile and even India, as well as artisan craft beer from RAR Brewing especially brewed for the event. Hoopers Island Oyster Aquaculture will be onsite shucking locally grown oysters, and other local fare will be available. Wine and beer will be available for both tasting and purchase.

The festival wraps up with an open-air jazz concert on Saturday from 5 to 7pm.

Ticket info – buy tickets online or in person at the Wine Bar, 414 Race St., Cambridge.

  • Small Plates Pairing Dinner – Friday: $75 per person (Ticket sales close May 12 for the dinner only)
  • Wine, Beer and Oysters Tasting – Saturday: $45. Includes admission to that evening’s Jazz Concert
  • Jazz Concert only – Saturday Night: $15 per person

The event is the brainchild of Ed Johnson and Randy Decker, owners of the Wine Bar in Cambridge.

Proceeds benefit programming at the Dorchester YMCA an the Dorchester Chamber Foundation.

For more information visit or the event page on Facebook.

Chillin' On The Choptank