Dinner Under the Stars

Dinner Under the Stars Al fresco dining on Wednesday evenings in the first block of West Street, Annapolis, Maryland.

Enjoy live music, entertainment and dining from mid May thru September 5pm to 9pm.

06/22/2026

Boot scoot your way across the dance floor on Wednesday while line dancing with Dean! Grab dinner first on the street - or bring a chair and have some fun! No experience necessary. Cowboy boots optional!

Tonight calls for clear skies🌞 + D'Vibe & Conga 6-9pm 🎻+ 7 fabulous restaurants with outdoor dining 🍽️ + YOU 👫= a fun ni...
06/17/2026

Tonight calls for clear skies🌞
+ D'Vibe & Conga 6-9pm 🎻
+ 7 fabulous restaurants with outdoor dining 🍽️
+ YOU 👫
= a fun night!

Outdoor dining starts at 5pm on historic West Street, Annapolis

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We will see you soon! Here's a list of music and fun on West Street for the rest of June and July....stay tuned for Aug...
06/16/2026

We will see you soon! Here's a list of music and fun on West Street for the rest of June and July....stay tuned for August! Make plans and dine and dance with us - full schedule at IWSAnnapolis.com

✨JUNE✨
Wednesday, June 17 - D'Vibe & Conga
Wednesday, June 24 - DJ and Line Dancing Lessons with Dean

✨JULY✨
Wednesday, July 1- Bayside Big Band
Wednesday, July 8 - localsoul
Wednesday, July 15 - Seth Kibel
Saturday, July 18 - Spice & The Motown Magic Concert
Wednesday, July 22 - Wendell Live - Sinatra Tribute Artist
​Wednesday, July 29 - DJ and Line Dancing Lessons with Dean

Visit Annapolis, Inner West Street Annapolis, Luna Blu Ristorante, Picante Annapolis, Stan and Joe's Saloon, Rams Head Tavern Annapolis, El Toro Bravo, Tsu , 49 West Coffeehouse, Winebar & Gallery, Annapolis Arts District

D'Vibe & Conga will fill the street with music this Wednesday- please join us 🍽️🎶✨ dining starts at 5pm and music plays...
06/16/2026

D'Vibe & Conga will fill the street with music this Wednesday- please join us 🍽️🎶✨ dining starts at 5pm and music plays 6-9pm

06/15/2026

We always have a fun night with D'Vibe & Conga at Dinner Under the Stars - grab a seat at one of our restaurants this Wednesday - you don't want to miss their performance! Make plans to dine at Luna Blu Ristorante, Picante Annapolis, Tsu , Rams Head Tavern Annapolis, El Toro Bravo, 49 West Coffeehouse, Winebar & Gallery, Stan and Joe's Saloon. Bring your sneakers and play a little Pickleball Under The Stars.

Due to storms rolling thru tonight, Wednesday, June 10th Dinner Under the Stars will be cancelled. You can still dine ...
06/10/2026

Due to storms rolling thru tonight, Wednesday, June 10th Dinner Under the Stars will be cancelled. You can still dine indoors! Reminder to make your reservations for Arts Annapolis on Saturday. From Noon til 10pm there is so much happening, check it out: https://www.iwsannapolis.com/event-details/arts-annapolis-2026

06/08/2026

✨This Wednesday 6-9pm Seth Kibel Quintet will take the stage at Dinner Under the Stars on historic West Street. Choose from Luna Blu Ristorante, Rams Head Tavern Annapolis, 49 West Coffeehouse, Winebar & Gallery, Tsu , El Toro Bravo, Picante Annapolis, Stan and Joe's Saloon! Dining starts at 5pm make plans for a night of dining and dancing with Inner West Street Annapolis✨

Coming to West Street on Wednesday, June 10th 6-9pm the entertaining Seth Kibel Quintet 🎷 Make your reservations now to ...
06/07/2026

Coming to West Street on Wednesday, June 10th 6-9pm the entertaining Seth Kibel Quintet 🎷 Make your reservations now to save your seat! Visit IWSAnnapolis.com to see a list of participating restaurants.

The artists had plenty of subjects for plein air painting last night 🎨. Everyone enjoyed peaking over their shoulders.
06/04/2026

The artists had plenty of subjects for plein air painting last night 🎨. Everyone enjoyed peaking over their shoulders.

Address

West Street And Calvert Street (Intersection)
Annapolis, MD
21401

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