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 on Fenwick Street, where the street will be shut down and music, food and more will be available for this fun street party. Businesses along the street will be open and the Fenwick Inn will be hosting a fun Jazz party with more music and fun!

THE FENWICK INN: 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 (while supplies last) and there will be a cocktail bar featuring the Inn’s signature jazz fest cocktail (the hurricane), beer and wine. Raymond Tuazon & Associates will help teach Swing Dance Lessons to singles and couples at the cocktail party.

HOW TO GET IN: Everyone is free to come to the street party, but space is limited at the Fenwick Inn.

- REGULAR ADMISSION: FREE to walk in! First come, first serve. Limited tickets available.
- VIP ADMISSION (SOLD OUT): Includes private seating in VIP section, VIP server, shrimp boil box (shrimp, cherrystone clams, mussels, corn on the cob, hush puppies & watermelon), 2 drink tokens (can be used on beer, wine or signature drink). $45 per person, plus applicable taxes & fees. Advanced registration required for VIP section. Space is limited to 40. Due to the nature of the event, tickets are not refundable. Tickets are transferable, just let us know the name of the person you are transferring your ticket to within 24hrs of the event. To purchase VIP tickets, CLICK HERE.

This event will be held outdoors under a pavilion and umbrellas. There is an entrance to the venue from the public parking lot, 41660 Park Ave, across from The Good Earth.

STREET PARTY: Outside the Fenwick Inn on Fenwick Street, the road will be shut down to traffic and open to everyone! Live jazz music from GrooveSpan will be playing along the street and there will be food available. Lots of businesses along Fenwick will be open with more jazz fun! SEE BELOW FOR LIST OF LEONARDTOWN BUSINESSES PARTICIPATING!

AFTER PARTY: Antoinette’s Garden will be hosting a Jazz Era After Party starting at 9 PM. Attendees who come in costume will receive 20% off their order.

COSTUME CONTEST & CASH PRIZES: The evening will be a celebration of jazz music throughout the 20s, 30s, 40s and 50s. 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 couples. While costumes are highly encouraged, they are not required. Complimentary accessories will be available at the Accessories Table while supplies last.