May Things To Do

The water is warming up, event season is in full swing, and the calendar is stacked, from May Day blooms to Blue Angels flyovers and waterfront festivals. Here’s what’s happening this month. ⚓🌼☀️

May Day in Annapolis 🌸

May 1, 2026

A beloved local tradition that transforms downtown into a living garden. Residents and businesses decorate their doors with handmade May baskets overflowing with fresh flowers. Walk through Downtown Annapolis, admire the blooms.

Mother’s Day Experiences 💐

May 10, 2026

Spend Mother's Day in a charming destination.

• Mother’s Day Afternoon Tea at the Maryland Inn
• Mother’s Day Brunch Cruise
• Mother’s Day Harbor Cruises
• Mother’s Day at Honey’s Harvest Farm
• “Mommy Time” at William Paca Garden
• Brunch or dinner at one of our local restaurants

Sailing Cruises ⛵

All Month Long

Cruises and sails run throughout the month, offering everything from relaxed sightseeing to curated themed experiences.

• America’s 250 Harbor Cruise
• Annapolis Harbor & USNA Cruise
• Chesapeake Bay Bridge Cruise
• Scenic Severn River Cruise
• Thomas Point Lighthouse Cruise
• Annapolis Private Sunset Cruise
• Monday History Sunset Sails
• Tuesday Beer Tasting Sunset Sails 
• Wednesday Night Races
• Acoustic Brunch Sail with Gareth Asher 

Commissioning Week and Blue Angels ✈️

May 15-22, 2026

One of the most anticipated weeks of the year in Annapolis, Commissioning Week brings high-energy celebrations to the waterfront.

Events:

• Blue Angels Practice Flights: May 19
• Blue Angels Flight Demonstration: May 20
• U.S. Naval Academy Graduation & Flyover: May 22
• US Naval Academy Band Armed Forces Day Concert 
• USNA Formal Color Parade 

On-the-water experiences during this time:

• Blue Angels Flotilla Paddle
• Sunrise & Blue Moon Paddles

Farmers Markets & Local Finds 🧺

Recurring Throughout May

Weekends here are built for wandering local markets and festivals.

• First Sunday Arts Festival
• ​First Sunday Farmers Market
• Third Sunday Farmers Market
• Anne Arundel County Farmers Market (Sundays)
• Annual Spring Craft Fair & Flea Market
• Anchors + Artisans

Tours, History & Outdoor Experiences 🏛️

All Month Long

Dive deeper into the destination with guided tours and outdoor exploration.

History & culture:

• African Americans in the Revolutionary War Tour
• William Paca Garden Tours
• Colonial Garden Party
• Scandalous Annapolis Walking Tour
• Brewer Hill Cemetery Tour

Outdoor:

• Bacon Ridge Natural Area (hiking + volunteer workday)
• Spring Garden Ramble at Historic London Town & Gardens
• Providence Spring Plant & Pottery Sale

Food, Culture & Events🐟

Throughout May

May delivers a strong mix of food, culture, and community-driven events.

• Chesapeake Catfish Cook-Off 
• ​Taste of Spring on West Street
• Dinner Under the Stars 
• Colonial Cocktails: Society Sippers
• Anne Arundel Asian American Festival
• Annapolis Irish Festival
• Brewgrass in the Barn

Arts, Music & Performances 🎨

All Month Long

The arts scene is in full swing with festivals, performances, and live music across the county.

• Annapolis Book Festival 
• Paint Annapolis + Dueling Brushes
• Cirque de Paris
• Candlelight Concert Series (Coldplay, Fleetwood Mac tributes)
• Rams Head On Stage shows
• The Bay Winds Band Spring Concert
• Live Arts Maryland: Timeless Brilliance
• Classic Theatre of Maryland: 42nd Street
• CP presents Poor Clare by Chiara Atik

Spring is blooming but don't forget to make your summer plans too! Tag us in your adventures @VisitAnnapolis or #VisitAnnapolis.