Come out to sample and meet the people behind the drink and food. Here you’ll find wine, beer and spirits events all over Maryland, from fairgrounds to farms, craft breweries, wineries and distilleries to small town Main Streets.
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September 2020
Classic Wooden Boat Regatta
Participate in the Classic Wooden Boat Regatta. The Woodwinds’ have been invited to participate in the race in the “Spirit of Tradition Class”. The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats to win the regatta. This…
Find out more »Wine & Unwind with Justin Ryan
Sip wine and enjoy live music with Justin Ryan! No fee, no reservation.
Find out more »2ND ANNUAL GUINNESS OKTOBERFEST
September 25th - 27th and October 2nd - 4th Join us as we transform our lawn into a German Beer Hall! Two exclusive beer releases, including one small-batch can release! Live music on each Saturday! Traditional German and Oktoberfest bites and meals! Please enjoy responsibly. Guinness Brewing Company, Baltimore, MD
Find out more »Acoustic Brunch Sail with Ernie Halter
Join us for an intimate, all ages acoustic show with Ernie Halter aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will perform for over an hour while at anchor in a secluded cove. After the performance we will set sail on the 74-foot, classic wooden schooner. Raise the sails, steer the boat, sit back, relax and meet Ernie while sailing the Bay. Enjoy a light brunch and Mimosas and…
Find out more »October 2020
First Friday in the Vineyard – Karaoke Ho Down
Join us for a western themed night of singing, dancing, and all around good times! Bring your dinner and snacks to complete the night. Wine available at the bar! No fee, registration required due to COVID restrictions.
Find out more »Lighthouse Cruise
Sail to as many as three different lighthouses on the Chesapeake Bay and learn about their history, importance, and present day condition by a guest lecturer from the Chesapeake Chapter of the U.S. Lighthouse Society. The sail includes a bagged lunch. Due to the Annapolis Power Boat Show, this sail departs from the Annapolis City Marina Departs at 11:30 am & returns at 3:30 pm at the Annapolis City Marina, 410 Severn Avenue, Annapolis MD 21403 Tickets are $100 per…
Find out more »Cocktail Cruising
Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail. Cocktail Cruise Menu: Black Bean Hummus Poblano Pimento Cheese Served with pita wedges and crostini Chicken Skewers with roasted veggies and tomato coulis Beef Skewers with roasted veggies and chimichuri sauce Great Assortment of Craft Beers from the Local Area, Wine and…
Find out more »Acoustic Brunch Sail with Tony Lucca
Join us for an intimate, all ages acoustic show with Tony Lucca aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will perform for over an hour while at anchor in a secluded cove. After the performance we will set sail on the 74-foot, classic wooden schooner. Raise the sails, steer the boat, sit back, relax and meet Tony while sailing the Bay. Tony Lucca is a Nashville-based singer/songwriter whose…
Find out more »13th Calvert Arts Festival: new date
New Octoberfest date: Come to the 13th Calvert Arts Festival Saturday, Oct 10, from 10 a.m. to 5 p.m., for the best Southern Maryland wines and craft beers. Shop from outstanding local juried artisans and food stalls inside and outside. Live entertainment, delicious food, children’s crafts, silent auction and more. Tour our 1692 church and labyrinth. Rain or shine! No admission fee. Proceeds benefit community projects. Free parking at historic All Saints’ Episcopal Church, Rts 2 & 4, Sunderland, MD.…
Find out more »Schooner Race Watch Cruise
The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! They will be racing to the Norfolk area, we will cheer them on till it’s time to go in. We will be under sail with…
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