Kick Off Jazz-Era Party on Fenwick Street in Downtown Leonardtown

The festivities kick-off with jazz-era fun in historic Leonardtown with a fun kickoff party at locations all up and down Fenwick Street, which will be closed off for a street party! The Fenwick Inn will host the main area of live music from the Chesapeake Orchestra Swing Combo and dance performances from 6:00 PM – 9:00 PM. Charcuterie boxes will be available for purchase and there will be a cocktail bar featuring the Inn’s signature cocktails.

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 their favorite period from the 20’s – 50’s. There will be a costume contest with cash prizes for the best dressed individual and couples. While costumes are highly encouraged, they are not required. Complimentary accessories will be available at the Accessories Table while supplies last.

Space is limited. There is no fee to attend, however, reservations are required. VIP Seating is available (fee required), contact the Inn at thefenwickinn@gmail.com for details. Please note that COVID-19 protocols will be observed for the event.

Meanwhile, Fenwick Street will be completely closed to traffic so attendees can enjoy all the fun and music from businesses up and down the street! Below is a list of all the fun you can expect!