Maryland May Events Guide 2026: What’s Happening Near You
What’s Happening Around Maryland This May
May is one of the best times of year to explore Central Maryland. From festivals and outdoor markets to live music and family fun, each county has something unique to offer. Here are some standout events happening this month:
Baltimore City
Baltimore comes alive in May with major festivals and can’t-miss events:
Artscape (May 24–26) – One of the largest free arts festivals in the country, featuring live music, art installations, performances, and food vendors throughout downtown.
FlowerMart at Mount Vernon Place (May 2–3) – A beloved spring tradition with flowers, local vendors, food, and family-friendly activities.
Baltimore Farmers’ Market & Bazaar (Sundays, May) – Under the JFX, this weekly market features fresh produce, local artisans, and some of the best food vendors in the city.
Baltimore County
Spring is in full bloom across Baltimore County with outdoor festivals and seasonal favorites:
Weber’s Farm Strawberry Festival (Late May, Parkville) – A local favorite with pick-your-own strawberries, food trucks, and kids’ activities.
Towson Spring Festival (Early May) – Live music, local food vendors, and family-friendly entertainment in the heart of Towson.
Oregon Ridge Nature Center Events (Throughout May) – Nature hikes, educational programs, and outdoor activities perfect for families.
Anne Arundel County
Waterfront charm and lively community events define May in Anne Arundel County:
Annapolis May Day Celebration (May 1) – Downtown Annapolis is filled with beautifully decorated flower baskets, local shopping, and festive spring vibes.
Maryland Craft Beer Festival (May 10, Annapolis) – Featuring dozens of local breweries, live music, and food vendors along the waterfront.
Annapolis Spring Sailboat Show Preview Events (Mid-May) – Smaller lead-up events and waterfront experiences celebrating boating season.
Harford County
Harford County offers classic community events and family-friendly fun:
Jarrettsville Lions Club Carnival (Mid-May) – Rides, games, food, and entertainment—a longtime local tradition.
First Fridays in Havre de Grace (May 3) – Shops stay open late with live music, food, and a lively downtown atmosphere.
Farmers Markets & Outdoor Events (Throughout May) – Seasonal markets and local gatherings across the county.
Howard County
Howard County brings a mix of music, food, and outdoor festivals:
Wine in the Woods (May 17–18, Columbia) – One of the region’s most popular wine festivals featuring Maryland wineries, live music, and artisan vendors.
Ellicott City Main Street Events (Throughout May) – Weekend events, live music, and pop-up markets in historic Ellicott City.
Lakefront Live Music Series (Columbia, Select Dates in May) – Outdoor concerts at the Columbia Lakefront—perfect for a relaxing evening.
From major festivals in Baltimore City to charming community events in Howard and Harford Counties, May is packed with opportunities to get outside and enjoy everything our area has to offer. Whether you're exploring with family, meeting friends, or discovering a new favorite spot, there’s no shortage of ways to make the most of the season.
