Jazzin’ Sunday in Town | Sunday, July 10, 2022

The weekend ends on a high “note” on Sunday when various businesses once again will host various jazz-themed activities, including jazz brunches and other activities.

The FREE Leonardtown Trolley will be circulating from 10am to 5pm at stops every 30 minutes. CLICK FOR MORE INFO, Stops & Track the Trolley


Sunday Jazz Cruises (3:00 p.m. – 5:00 p.m. AND 6:00 p.m. – 8:00 p.m.): Leonardtown Wharf, 22500 Washington Street, Leonardtown, MD 20650

  • Enhance your 3-day jazz weekend with a two-hour cruise on beautiful Breton Bay right from the Wharf while enjoying live jazz music, light fare and refreshments. You’ll be joined by our very own Wynne Briscoe, the Jazz Ambassador for the Potomac Jazz & Seafood Festival, during the trip. Beer, wine and light fare will be provided.

Jazz Activities around Leonardtown (All Day)

  • Enjoy jazz brunches, live music, activities and much more around town to finish out your weekend! Participating businesses will be listed below when updated!

The Front Porch Restaurant

Enjoy a jazz brunch at one of Leonardtown’s finest restaurants located in the historic Sterling House featuring live jazz music while you dine from the Van Williamson Jazz Duo from 10:00 a.m. to 1:00 p.m.


The Rex

Enjoy a jazz brunch at one of Leonardtown’s top restaurants featuring live jazz music while you dine from Funkzilla from 11:00 a.m. to 2:00 p.m.


The Slice House

Enjoy a special lunch of pizza, craft beer, cocktails, Bloody Mary’s, mimosas and more with live DJ music from Juicebox Johnson from 11:00 a.m. to 3:00 p.m.


Antoinette’s Garden

Antoinette’s Garden is a gourmet coffee and wine café with pastries, charcuterie and more featuring mimosas and great food! Dine indoors or enjoy dining on the historic Leonardtown Square where you can hear the music from the Rex.


Port of Leonardtown Winery

Local winery and agricultural cooperative will host a day of jazzy fun at their tasting room and outdoor patio and lawn area featuring live band GrooveSpan playing jazz hits from 2:00 p.m. to 5:00 p.m. Wine tastings, lawn games and more all day!


Old Towne Pub

Head on over to the Old Towne Pub, one of Leonardtown’s favorite spots, for lunch! Lots of beer, great food (award winning wings!) and more.


Board & Brush Creative Studio Leonardtown

Head to Board & Brush and try your hand at a special board activity you can take home! Sign up for the class below.


Spice Fitness Studios

Finish your weekend with some exercise in the fresh Southern Maryland air at the Leonardtown Wharf with a 1920s Flapper Outdoor Barre class beginning at 7:30 a.m. Sign up at the website below!


Fenwick Street Used Books & Music

Check out Fenwick Street Used Books & Music near the Leonardtown Square for a wide variety of jazz records on vinyl, many of which would be great for collectors!


Shepherd’s Old Field Market

An afternoon at Shepherds Old Field Market, an historic warehouse and hardware store rehabbed into an indoor marketplace and community gathering space that contains over 75 shops, a deli, coffee shop, beer garden, ice cream and more.


The Old Jail Museum & Leonardtown Visitor Center

Come check out this fascinating historic site right in the heart of Leonardtown! Built in 1876 and in use until 1945 by the oldest sheriff’s office in the nation, this granite block and brick structure retains its original upstairs cells where prisoners were once segregated by gender and race. The jail keeper’s quarters downstairs house related artifacts. Check out the Museum Store for souvenirs. ADMISSION IS FREE.

240-925-3427 | WEBSITE ⇒