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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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Hi Mamas! 👋

Looking for the perfect spot to fuel up after a stroll down Main Street or a busy day of soccer practice? We want to give a huge shoutout to our friends and community supporters at Federal House Bar & Grille! 🏛️🍔

Spring is in the air, and "Federal House Restaurant" is ready with everything we love about downtown Annapolis:

🍓 New Seasonal Menus: From fresh, vibrant dishes to the latest craft beer rotations and signature spring cocktails, there is something new to try on every visit! 🍹🍻

☀️ The Ultimate Outdoor Setup: Enjoy their shaded outdoor seating for a breezy lunch, or grab one of their fire pit tables for those cozy cooler nights under the stars. 🔥✨

🎓 Calling all Navy Families: A massive CONGRATULATIONS to the Class of 2026! ⚓️ White Works and Commissioning Week are right around the corner—Federal House is the perfect place to celebrate your Midshipman’s big milestone. Make sure to stop by and toast to the graduates! 🥂

Whether you're planning a date night, a family dinner, or a graduation celebration, Federal House always feels like home.

📍 Located in the heart of the historic district
💻 Check out the new menu: federalhouse.com

#AnnapolisMoms #FederalHouse #USNA #NavyGraduation #AnnapolisEats #SupportLocal #DowntownAnnapolis #CommissioningWeek
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Struck a pose and channeled our inner Miranda Priestly energy for the ultimate Moms Night Out 💋✨

We had the BEST time at the premiere screening of The Devil Wears Prada at @amctheatres in @shopatannapolismall iconic fashion, a little drama, and all the vibes 👠

Grab your girls, get the large popcorn (non-negotiable 🍿), and go see it for yourself. Trust us… we highly recommend. 💅
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