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Dinner Under the
Stars

Wednesdays and Saturdays
6-10pm
May 20 thru September
Some with themed nights

 

The first block of Annapolis’ historic West Steet is where families and friends meet Wednesday and 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
Reynolds Tavern.

Be sure to check out Curate for coffee and deserts. 

Learn to paint during Dinner Under the Stars at Wine & Design, take a game room challenge at Mission Escape Room, and check out new art exhibits at The Annapolis Collection Gallery, 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 you in 2024
New schedule to come!

Schedule

Coming Soon

Dance the night away under the stars

Musician

MAY 

Saturday, May 20

Pure Motown

with Moonie & Friends 

Wednesday, May 24

Naptown Brass Band

Saturday, May 27

Naptown Funk

Wednesday, May 31

Spice Trio

JUNE

Saturday, June 3

Rose Moraes

Brazilian Connection

 

Wednesday, June 7

Timmie Metz

and Tambo Trio

 

Saturday, June 10

Dueling Keyboards 

5pm

Bayside Big Band

6pm

Ballet Theater of Maryland 

7pm

 

Wednesday, June 14

Wendall Live

Sponsored by

Atlantic Prime Mortgage

 

Saturday, June 17

Chris Sacks Band

Sponsored by

Severn River ENT

 

Wednesday, June 21

Them Crazy Maracas

 

Saturday, June 24

Soul Journers

 

Wednesday, June 28

Moxie Blues Band 

Sponsored by

Campion Hruby

Landscape Architects

JULY

Saturday, July 1

Chris Sacks Band

Wednesday, July 5

Timmie Metz

and Tambo Trio

Saturday, July 8

Soul Journers

Wednesday, July 12

Troll Tribe

Saturday,July 15

Island Breeze

Wednesday, July 19

Wendall Live

Saturday, July 22

Rose Moraes

Brazilian Connection

Wednesday, July 26 

JazzMaTazz

Larry Haavik

Saturday, July 29

Naptown Funk

AUGUST

Wednesday, August 2

Spice Trio

Saturday, August 5

Soul Journers

Wednesday, August 9

Wendall Live

Saturday, August 12

Chris Sacks Band

Wednesday, August 16

Them Crazy Maracas

Saturday, August 19

Bayside Big Band

Wednesday, August 23

Island Breeze

Saturday, August 26

Rose Moraes

Brazilian Connection

Wednesday, August 30

Spice Trio 

and special guest

Songbird

SEPTEMBER

Saturday, September 2

Geno Marriott

The Spirit of Jazz

Wednesday, September 6

Spice Trio

Saturday, September 9

Soul Journers

Wed, September 13

Rose Moraes

Brazilian Connection

Saturday, September 16

Annapolis

Songwriters Festival

Wed, September 20

Wendall Live

Saturday, September 23

The Spindles

Motown Concert

Wednesday, September 27

Spice Trio

Saturday, September 30

The Spindles

Motown Concert

Cancelled Due to Rain

Cancelled Due to Rain

Cancelled Due to heat! 

Cancelled Due to Rain

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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