GrooveSpan (Full Band) at Port of Leonardtown Winery

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Port of Leonardtown Winery, 23190 Newtowne Neck Rd, Leonardtown, MD

GrooveSpan (full band!) will get you groovin' at the Port of Leonardtown Winery to celebrate the Potomac Jazz Festival!

GrooveSpan (full band!) performs an all jazz program at Port of Leonardtown Winery , 1:00 – 4:00pm to bring the Potomac Jazz Fest celebration to a close! The full band - plus special guest performers - will get you swingin' and groovin' as you enjoy your favorite savories and beverages all afternoon!

Goud Cheese food truck & CiCi's Sugar Shack will be on location with yummy food & sweets to enjoy. Wine tastings, frose` slushies & your favorite wine will be awaiting. Family/pet friendly


Leonardtown is host to jazz-era fun in historic Downtown Leonardtown with the Official Kick-off Party for the Potomac Jazz & Seafood Festival Weekend Celebration on Friday, July 9, 2021. The evening will be a celebration of jazz music throughout the 20’s, 30’s, 40’s and 50’s. Everyone is invited to come dressed in attire from those periods and there will be a costume contest with cash prizes for the best dressed individual and couple. (Costumes highly encouraged, but not required.) Complimentary accessories will be available at the Accessories Table in front of Town Cleaners while supplies last.

5:00 – 8:00pm -- Fenwick Street street will come alive with music, food and activities for all! - GrooveSpan Trio performs at North End Gallery - Classic antique car show sponsored by the St Mary’s Rod & Classic - Olde Town Pub’s Wing Wagon offering delicious wings and light fare, - Social Coffeehouse & Cocktail Bar offering coffeehouse menu and cocktails - Businesses along the street open and offering jazz related activities and promotions.

6:00 – 9:00pm Fenwick Inn (41685 Fenwick Street), hosts a Jazz Era Cocktail Party featuring live music by the Chesapeake Orchestra “Swing Combo” and swing dance lessons for singles and couples, courtesy of Raymond Tuazon and his team from the Dance Collective. Charcuterie boxes will be available for purchase (while supplies last) plus a cocktail bar featuring the Fenwick Inn’s signature jazz fest cocktail (the Hurricane), beer and wine. Additional winners will be chosen for best jazz era costumes from the periods noted above with cash prizes once again awarded to the best dressed individual and couple.

This event is FREE and open to the public, but please note that space is limited at the Fenwick Inn. 9:00pm onward…

The party continues at Antoinette’s Garden in Leonardtown Square (22694 Washington St.) for the official Jazz Era After Party. Enjoy jazz in the Garden and sample delicious gourmet coffee and wine. Antoinette’s also offers charcuterie boards and an assortment of tempting desserts – sure to offer a sweet ending to a wonderful evening.

SUNDAY, JULY 11th… The weekend ends on a high “note” on Sunday when the Town of Leonardtown once again will host various jazz-themed activities, including jazz brunches, a flapper-style barre class, live music, art shows and more around town. Join us for a weekend of jazz, dazzle and glamor throughout Leonardtown on Friday, July 9th and Sunday, July 11th! We hope to see you there!

GrooveSpan: Potomac Jazz & Seafood Festival visit: North End Gallery: Port of Leonardtown Winery:

More About This Prestigious Event: St. Mary’s County Museum Division, The Town of Leonardtown, and Visit St. Mary’s are proud to partner again on the three-day celebration for the 21st Annual Potomac Jazz & Seafood Festival. This special event, first held in 2019, was selected to win the prestigious “Maximizing Opportunities Award” from the Maryland State Office of Tourism for successfully taking advantage of an existing event to generate overnight stays to a destination and leveraging partnerships. The three partners are VERY happy to be back in action, working together to bring this exciting three-day weekend celebration back to the community.