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Dinner Under the
Stars
Wednesday Evenings
6-10pm
May 21 thru September 24
with Special Saturday night
Dinner Under the Stars Concerts
The first block of Annapolis’ historic West Steet is where families and friends meet Wednesday and several Saturday evenings, from May to September, to relax, dine under the stars, dance and enjoy live music. It’s a tradition - when the summer sun sets, a canopy of overhead lights add romance to every evening of Dinner Under the Stars. Outdoor space is limited, reservations are recommended. Call the restaurant of your choice to reserve your table.
Participating restaurants will give you a wide choice of international and hometown flavors. Make your reservations for Dinner Under the Stars with the following participating restaurants:
Nearby restaurants with additional outdoor dining include:
-
Level a Small Plates Lounge - Takes Reservations (2nd block of West Street) - Live Music Wednesdays 6pm - 9pm (rain or shine)
-
Reynolds Tavern (Top of West Street) - Live Music Wednesday-Saturday
-
Curate (3rd block of West Street) - Coffee and Desserts
Learn to paint during Dinner Under the Stars with Gallery 57 West (check the gallery for upcoming schedule), take a game room challenge at Mission Escape Room, and check out new art exhibits at The Annapolis Collection Gallery, Annapolis Pearl Gallery and Gallery 57 West, 49 West Coffeehouse Winebar & Gallery, Tsunami, and Level.

Dinner Under the Stars Music and Entertainment
Music is 6pm-9pm unless otherwise indicated
Wednesday Nights, music is down by Stan and Joe's Saloon and
Saturday Nights music is in front of the Art Galleries - see below
Dance the night away under the stars
2025 Music Schedule
If you would like to sponsor a night of Dinner Under the Stars contact Audrey Lee at audrey@innerweststreetassociation.com
Schedule
Coming Soon

MAY
Wednesday, May 21
D'Vibe and Conga
Wednesday, May 28
Spice Band
JUNE
Wednesday, June 4
Spirit of Jazz
with
Geno Marriott
Wednesday, June 11
Timmie, Tambo and Erich
Saturday, June 14
A CELEBRATION
OF THE ARTS
Bayside Big Band
Wednesday, June 18
Wendall Live
(Frank Sinatra Tribute)
Wednesday, June 25
Spice Band
JULY
Wednesday, July 3
Seth Kibel & The Kleztet
Wednesday, July 9
D'Vide and Conga
Wednesday July 16
Timmie, Tambo and Erich
Saturday, July 19
MOTOWN CONCERT
The Groove Spot Band
and Show
Wednesday, July 23
Spirit of Jazz
with
Geno Marriott
Wednesday, July 30
Spice Band
AUGUST
Wednesday, August 6
Wendall Live
Frank Sinatra Tribute
Wednesday, August 13
Seth Kibel & The Kleztet
Saturday, August 16
LET'S SALSA
TBD
Wednesday, August 20
Juliet Lloyd
Wednesday, August 27
SoulJourners
SEPTEMBER
Wednesday, Sept .3
Seth Kibel & The Kleztet
Wednesday, Sept. 10
Timmie, Tambo and Erich
Saturday, September 13
Annapolis Songwriters
Festival 5-10pm
Music on the end at Calvert and West St.
Wednesday, Sept. 17
Spice Band
Wednesday, Sept. 25
SoulJourners
PICKLEBALL
UNDER THE STARS
Join Annapolis Pickleball Club for a night of friendship and fun!
Pickleball courts will be marked out at the top of West Steet, outside Sadona Salon + Spa, every Wednesday from
5 pm - late.
Enjoy a Dinner Under the Stars and a cold beer after you slam, defend, and dink to victory!


