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Dinner Under the
Stars
Wednesday Evenings
6-10pm
May 20 thru September 30
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) - Wednesday nights at Reynolds Tavern come alive with the smooth sounds of the Unified Jazz Ensemble from 6:30pm–9:30pm. Join us for an evening of exceptional live jazz, warm ambiance, and timeless charm in the 1747 Pub—or in the Courtyard, weather permitting. $10 cover; no cover for our fine dining guests.
-
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
Music is set up in front of Mission Escape
Dance the night away under the stars
2026 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 20
Voices for Vets
Wednesday, May 27
Join us for a night of
Line Dance lessons
with Dean Garrish
JUNE
Wednesday, June 3
Local Souls
Wednesday, June 10
Seth Kible & The Kleztet
Saturday, June 13
A CELEBRATION
OF THE ARTS
TBD
Wednesday, June 17
D'Vibe and Conga
Wednesday, June 24
Join us for a night of
Line Dance lessons
with Dean Garrish
JULY
Wednesday, July 1
Bayside Big Band
Wednesday, July 8
Local Souls
Wednesday July 15
Seth Kibel and the Kleztet
Saturday, July 18
MOTOWN CONCERT
Spice Band
and Friends
Wednesday, July 22
Wendall Live
Frank Sinatra Tribute
Wednesday, July 29
Join us for a night of
Line Dance lessons
with Dean Garrish
AUGUST
Wednesday, August 5
Guava Jelly
Wednesday, August 12
SoulJourners
Saturday, August 15
LET'S SALSA
TBD
Wednesday, August 19
D'Vibe and Conga
Wednesday, August 26
Join us for a night of
Line Dance lessons
with Dean Garrish
SEPTEMBER
Wednesday, Sept. 2
Seth Kibel & The Kleztet
Wednesday, Sept. 9
Spice Band
Saturday, September 12
Annapolis
Songwriters Festival
5-10pm
Music on the end at Calvert and West St.
Wednesday, Sept. 16
SoulJourners
Wednesday, Sept. 23
Guava Jelly
Wednesday, Sept. 30
Join us for a night of
Line Dance lessons
with Dean Garrish

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!




