Annapolis is quickly becoming a festival town, and we take great 'Pride' in our annual parades. And this year, we're excited to see the return of the Annapolis Pride Parade and Festival. Recently named “Best Local Day Trip” in the Washington Blade’s LGBTQ DC Reader’s Choice Awards.

 

1.  It’s the Only Day You’ll See More Rainbow Flags Than Maryland Flags (and Maybe a Few Pumpkins Too) 

It’s no secret Marylanders are passionate about their flag but Annapolis Pride takes the crown. Watch our charming bayside city transform the cobblestone streets of downtown into a runway of love, music, and pure celebration with a splash of Halloween flair! 

 

2. Cooler Weather, Hotter Vibes

We’ve moved the parade and festival to October 18, which means less heat and more time to party! Enjoy Pride without the summer scorch and dance the night away in perfect fall weather. 

 

3. 2025 Theme: Growing in Pride, Growing in Community 

This year’s theme reminds us that even in the face of oppression, we thrive, uplift one another, and protect our community. Pride is rooted in resilience and resistance and this October, we’re growing in pride and pumpkins, reaffirming that everyone deserves to live openly, safely, and proudly. With our fall date, you can celebrate Annapolis Pride without competing with other summer Pride events just pure, hometown joy. 

 

4. Out of This World Grand Marshal 

Col. Bree Fram, astronautical engineer, author, podcaster, speaker, and retired U.S. Space Force colonel, will serve as this year’s Grand Marshal—definitely someone you’ll want to see leading the parade! 

 

5. Unforgettable Parade Energy 

Colorful floats, unicorns, draft horses, dancers, marching bands, and maybe even a few skeletons or witches joining the lineup. Annapolis Pride’s parade is a vibrant display of joy, resilience, and unity you won’t want to miss.

 

6. Incredible Live Entertainment 

Catch talented performers like The Gathering Gloom, a Cure Tribute band, and countless other artists lighting up three festival stages throughout the afternoon. 

 

7. Food, Drinks & Absolute 21+ Area 

Annapolis brings the flavor! Come hungry for everything from funnel cakes to international bites brought to you by 20+ food trucks. Plus, enjoy a dedicated 21+ area with specialty cocktails and adult-friendly entertainment—a perfect place to celebrate Pride in a grown-up way. 

 

8. Shop Local & LGBTQIA+ Vendors 

Discover unique art, crafts, clothing, and Pride merch from nearly 200 local artisans and creators, plus some frightfully festive finds. 

 

9. Family-Friendly Fun 

From kids’ activities (including free face painting at the Visitor's Center on West Street to community booths and Halloween-themed crafts, there’s something for everyone to enjoy in a safe, inclusive space. Costumes encouraged! 

 

10. Visit the Pumpkins, Take a Haunted Stroll, and Soak Up the Magic 

Make a weekend of it! Visit the decorated pumpkins around town, take a haunted stroll through historic Annapolis, and end your night surrounded by Pride lights and laughter. If you’re going to celebrate love and inclusion, you might as well do it with a touch of Halloween enchantment. 

Annapolis Pride

The Annapolis Pride Parade celebrates the LGBTQ+ community, engaging residents, businesses, and groups to unite in welcoming and embracing diversity in Annapolis.