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Do Not Miss

Dinner Under the Stars: An Annapolis Tradition

May 22, 2023 by Jessica Opert
Dinner in Downtown Annapolis

Hungry for food, music and a beautiful outdoor setting? If you haven’t been yet, there is still plenty of time to take advantage of Dinner Under Stars brought to you by Inner West Street Association. 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!

  • Luna Blu Ristorante
  • Tsunami Sushi Bar and Lounge
  • 49 West Coffeehouse Winebar & Gallery
  • Stan and Joe’s Saloon
  • Rams Head Tavern
  • Picante Annapolis
  • Level

Nearby restaurants with additional outdoor dining include Reynolds Tavern.

And be sure to check out Curate for coffee and desserts. 

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.

Please check out the Music and Entertainment calendar for dates and times (mostly 6 PM – 9PM) of all the live bands performing.

Wednesdays and Saturdays

May 20 thru September 23, 2023

6-10pm

Some with themed nights

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Related posts:

Navigating the Annapolis Songwriter Festival   ArtFarm Annapolis: Cultivating Creativity and Community  September is Time for a Fresh Start   Hyatt Regency Chesapeake Bay Resort and Marina
Category: Do Not Miss See all posts by Jessica Opert

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Our Community Suppor

Our Community Supporter, Davy Dance Academy, is bringing a little holiday magic to the stage with their Polar Express Holiday Musical! 🚂✨

🎟️ Tickets are on sale now!
📅 Saturday, December 19, 2026
⏰ 2:00 PM & 6:00 PM
📍 Anne Arundel Community College
🎫 Tickets: $15 kids (ages 2–12) & $20 adults

🔗 Get your tickets here: 22055.recitalticketing.com

We love seeing local businesses like Davy Dance Academy bring our community together through the arts. ❤️

#AnnapolisMoms #AnnapolisDance #HolidayMusical
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A LITTLE CULTURE, A LITTLE COMEDY, AND SOME HOLIDAY SHOPPING — WHAT’S ON YOUR WEEKEND CALENDAR? 👀

There’s a good mix of things happening around Annapolis this weekend, from live performances and local shopping to wine tastings and a celebration of Indigenous arts.

Here’s what’s coming up November 13–15:

🎭 Oklahoma! at Maryland Hall
🍷 Tastings & Tunes: Wine & Beer Fest on West
🎁 Holiday Pop-Up Shop at Severna Park Community Center
😂 Comedian Paul Mecurio at Rams Head on Stage
🥁 Uhwachi-Reh Indigenous Arts at Pip Moyer Recreation Center

There’s a little something for every kind of weekend plan, so take your pick and get those dates on the calendar!

👉 See the full Do Not Miss List here: annapolismomsmedia.com/do-not-miss-list-november-12-2026/

#AnnapolisMoms #DoNotMissList #AnnapolisEvents #WeekendPlans #ThingsToDoAnnapolis
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