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What's Up Magazine

Dining Scene Eastern Shore: Wine tastings, festivals, barn parties, and more

Oct 07, 2015 04:00PM ● By Cate Reynolds

Pence, Pear, Patio Wine Tasting at the Bartlett Pear Inn

Join the Bartlett Pear Inn on Friday, October 9 at 6 PM for a wine tasting with friend Stephen James, general manager from Pence Ranch in Santa Barbara, California. The cost is $60 per person for wine tasting and heavy canapés in cocktail party style. Stay for dinner and enjoy 20% off your meal. Reservations are required and there is limited space on the patio. Ladies are advised to bring a wrap as the event is scheduled to be outdoors. In the event of rain, guests will gather in the bar.

6th Annual Food & Wine Festival at Simpatico

Taste over 50 Italian wines, Limoncello, Bellinis, “made in Italy” food and artisan cheeses from Simpatico on Saturday, October 10 from 12 to 5 PM. Enjoy food demonstrations from local chefs, bocce ball, Italian trivia contest with prizes, an art competition, and live Italian music. Admission is $25 for adults, $10 for designated drivers, and kids are free. Tickets cover all tastings, food, and activities. Call (410) 745-0345, email, or visit to purchase tickets.

Barn Party at Triple Creek Winery

Come out to Triple Creek Winery for games, live music, a DJ, and a contest for best cowboy/girl costume on Saturday, October 10 starting at 6pm

Pickering Creek’s Annual Harvest Hoedown Festival

Enjoy crafts, kids activities, bluegrass music, hay wagon rides, food, and more on Sunday, October 11 from 11 AM to 4 PM. Fun for the whole family! $10 per car. Rain or shine. Call (410) 822-4903 for more information.

Tilghman Watermen’s Museum Presents: Tastes of Tilghman

Come and enjoy a taste of stories from local watermen, a taste of crafts that watermen use daily, a taste of wine, beer, and hors d’oeurves, and a taste of local music by Shelley Abbott at the Black Walnut Point Inn on Sunday, October 11 from 4 to 7 PM. Tickets are $45 each, $80 per couple available at Two If By Sea Café, Tilghman Island Country Store, and the Museum at the Lee House. Tickets include entertainment, food, wine, beer, and door prizes. Advanced Tickets Only!