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Arts & Entertainment, Do Not Miss, Halloween, Holiday

Masquerade…Annapolitans on Parade

October 23, 2023 by Jamie Alvarenga

By Jamie Alvarenga

Could you use a mom’s night out or date night? If so, check out the Dinner Under the Stars Masquerade Ball happening this Saturday, October 28, 5-10 PM along West Street in Annapolis. Save the date, gather some friends, and enjoy a night full of live entertainment under the stars. Pssst… you’ll want to leave the kids at home for this one!

dinner under the stars
Patrons enjoy dinner under the stars on a recent Saturday…but the dress code this weekend will have a lot more pizzazz! Image via Inner West Street Annapolis / Facebook

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The first block of West Street, known as Inner West Street, is a charming area in downtown Annapolis. It’s full of delicious dining options, outdoor seating, twinkling lights, and is the perfect place for an enchanting evening. There’s always something fun going on here, and the most entertaining event yet is happening this Saturday.

There are plenty of places to dine (and drink!) during the Masquerade Ball & Drag Show, including Luna Blu Ristorante, Picante Annapolis, Rams Head Tavern, Tsunami, 49 West Coffee and Wine Bar, and Stan and Joe’s Saloon. Keep in mind that most restaurants have a two-hour dining limit. 

The Ball will be a great opportunity for a ladies night…with fancy dress!
Image via Canva

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The festivities will be alternating from live music, to drag shows, and even a ballet performance. Here’s a look at the schedule:

5:30-6:30: Bayside Big Band

6:30-7:00: Drag Show #1

7:00-8:00: Bayside Big Band with Ballet Performance

8:00-8:30: Drag Show #2

8:30-9:00: Bayside Big Band

9:00-9:30: Drag Show #3

Dress to impress because there will also be costume contests. Masquerade masks, feathers, sequins, or anything sparkly is encouraged. And don’t miss out on the raffle for $1,000 worth of gift cards! 

Al fresco dining, music, drag shows, AND fancy costumes? This event sounds like a blast, especially for parents who deserve to let loose–treat yourself to a bit of whimsical fun under the stars!

Learn more about the Masquerade Ball & Drag Show at Inner West Street by visiting the official website. You can also follow IWS on Facebook to stay up-to-date on more upcoming festivities. 

Inner West Street’s first Masquerade Ball will be a night to remember! Image via Inner West Street Annapolis / Facebook

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Kids trick or treating and running10 Trunk-or-Treats Coming Up In The Annapolis Area Chocolate binge festival people around a fire pit making s'moresChocolate Binge Festival Returns with Sweets for All Carriages on West Street Thanksgiving paradePasadena Thanksgiving Day Parade
Category: Arts & Entertainment, Do Not Miss, Halloween, HolidayTag: Activities, Event, Outdoors See all posts by Jamie Alvarenga

About Jamie Alvarenga

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