A Local’s Guide to Festivals in Annapolis All Year Long.

🎉 Why Annapolis Festivals Are a Must-Experience

Annapolis isn’t just Maryland’s capital — it’s a vibrant, waterfront city with deep historical roots, a thriving arts scene, and a strong sense of community. One of the best ways to experience the local flavor is through its festivals, which happen year-round and celebrate everything from maritime heritage to crab feasts, music, and culture.

Whether you're a local homeowner or thinking of relocating to Annapolis, these annual events are part of what makes life here special.

🌸 Spring Festivals in Annapolis

Annapolis Film Festival (March/April)
This cinematic celebration brings independent filmmakers and movie lovers together for a multi-day event in downtown Annapolis. Expect screenings, Q&A panels, and parties.

Spring Sailboat Show (April)
Nautical lovers rejoice! This show features stunning sailboats, sailing gear, and expert talks — all set in historic Ego Alley.

☀️ Summer Festivals in Annapolis

Annapolis Arts Week (June)
A full week dedicated to art, music, and creativity. Enjoy gallery tours, live mural painting, artisan markets, and outdoor performances.

Fourth of July Parade & Fireworks
An iconic Annapolis tradition with a patriotic parade, live music, and fireworks over the harbor.

Maryland Crabs & Beer Festival (August)
Celebrate Maryland’s favorite crustacean with all-you-can-eat crabs, cold beer, live music, and games. A local summer favorite!

🍁 Fall Festivals in Annapolis

Annapolis Boat Shows (October)
Both the United States Powerboat Show and United States Sailboat Show happen in October and are two of the biggest boat shows in the country. These events attract boating enthusiasts and buyers from all over the East Coast.

Fall Fest at Homestead Gardens (September–October)
Family-friendly fall fun with hayrides, pumpkin patches, live music, and food trucks.

❄️ Winter Festivals & Holiday Events

Midnight Madness (December)
Downtown Annapolis transforms into a festive holiday shopping district with twinkling lights, late-night deals, and live entertainment.

Eastport Yacht Club Lights Parade (December)
A uniquely Annapolis tradition — watch boats decked out in holiday lights sail along Spa Creek. It’s magical, creative, and a community favorite.

Chocolate Binge Festival (December)
Enjoy sweet treats, live music, artisan vendors, and even a holiday light canopy. This quirky festival is perfect for families and foodies alike.

🗓️ Plan Your Year Around the Fun
Living in Annapolis means you’ll never run out of events to enjoy. These festivals not only offer entertainment — they also strengthen community bonds and celebrate the spirit of the city.

🏠 Thinking of Moving to Annapolis?
Festivals are just one of the many reasons people fall in love with Annapolis. From walkable waterfront streets to award-winning schools and historic homes, there’s something for everyone here. If you're house hunting in a city that knows how to mix charm with celebration, Annapolis is a top choice.