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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:

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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

Musician

MAY 

​

Wednesday, May 20

Voices for Vets

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Wednesday, May 27

Join us for a night of

Line Dance lessons 

with Dean Garrish

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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

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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

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​

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

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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! 

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©2025 by Inner West Street Association

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