April in Annapolis & Anne Arundel County is when spring energy hits its stride. Follow revolutionary stories along the Be Revolutionary: America250 Exploration Trail Pass, wander the docks during the Annapolis Spring Boat Show, and come hungry for the Maryland Chicken Wing Festival and Maryland Pizza and Pints Festival. Here’s what’s happening this month around town. ⚓🍗🍕🌷 

 

🏛️Explore Revolutionary Stories Across the Destination 

March 19, 2026 - December 31, 2026

July 4, 2026 marks a milestone moment as the United States celebrates its 250th birthday. The Be Revolutionary: America250 Exploration Trail Pass is your key to discovering revolutionary stories across Annapolis and Anne Arundel County. Use our free mobile pass guides you to historic sites, cultural landmarks, small businesses, and scenic spots.

Plus, your adventures earn rewards along the way: 

  • 13 sites | 1,300 points: A 4-pack of stickers celebrating our past, present, and future 

  • 25 sites | 2,500 points: “Be Revolutionary” socks

  • 50+ sites | 5,000 points: A commemorative “Be Revolutionary” YETI mug to toast your success 

It’s a playful, interactive way to explore history while collecting keepsakes that celebrate your journey. 

 

⛵Annapolis Spring Sailboat Show 

April 24–26, 2026 

One of the most iconic spring events in the sailing world returns to the waterfront during the Annapolis Spring Boat Show. 

Held at City Dock in the heart of historic Annapolis, the show features dozens of sailboats, cruising yachts, and maritime vendors. Visitors can step aboard vessels, browse the latest boating gear, meet sailing experts, and enjoy stunning Chesapeake Bay views. Even if you’re not a sailor, strolling the docks and soaking in the waterfront ambiance is a must this spring. 

 

🍗Maryland Chicken Wing Festival 

 April 18–19, 2026 

Get ready for bold flavors at the Maryland Chicken Wing Festival. 

Sample wings in every style; smoky, sweet, spicy, or tangy while enjoying live music, contests, and family-friendly fun. This high-energy festival is perfect for wing lovers and anyone ready to experience the best of local food culture. 

 

🍕 Maryland Pizza and Pints Festival 

April 19, 2026 

Right alongside the wing festival, the Maryland Pizza and Pints Festival pairs two of life’s greatest pleasures: pizza and craft beer. Sample a variety of pies from local restaurants, sip regional brews, and enjoy live entertainment. It’s the perfect way to spend a sunny spring day with friends and family.  

 

Even More Things to Do This Month

Beyond these signature events, April is packed with ways to experience Annapolis and Anne Arundel County: 

  • Outdoor adventures along scenic trails and waterways 

  • Waterfront dining as patio season returns 

  • Local art galleries, museums, and historic tours 

  • Live music and seasonal markets around town 

Looking for even more events? Browse the full events calendar to plan your next spring adventure in Annapolis & Anne Arundel County. ⚓🌷