| Start Date and Time | Event Details | Location |
|
| All Day | Charles County Fair (Multi-Day Event) | |
| All Day | Delmarva Bike Week (Multi-Day Event) | |
| All Day | Antiques Appraisal Day | |
| All Day | Harvest Festival at Layton's Chance Winery | |
| All Day | Heavy Seas Pints, Pyrates & Pigs | |
| All Day | In the Street Festival | |
| All Day | Indian Discovery Day | |
| Start Day | Native American Festival (Multi-Day Event) | |
| All Day | The Annapolis Craft Beer and Music Festival | |
| All Day | The Annual Downtown Hyattsville Arts Festival | |
| 8:00 AM - 2:30 PM | 27th Annual Maryland Lupus Summit - Baltimore | 720 Rutland Avenue Baltimore, MD (Johns Hopkins Turner Auditorium) |
| 8:00 AM - 12:00 PM | Home Depot's National Preparedness Month Outreach - Laurel | Home Depot 210 Ft. Meade Road Laurel, MD |
| 9:00 AM - 1:00 PM | Ellicott City Old Town Market - May 10 - Nov 8 | |
| 9:00 AM - 1:00 PM | Farmers Market | |
| 9:00 AM - 3:00 PM | Fenton Street Farmers Market - Silver Spring | Fenton Street and Ellsworth Drive Silver Spring, MD (Veterans Plaza) |
| 10:00 AM - 1:00 PM | 2nd Annual River Hill Health Fair - Clarksville | River Hill Village Center, Daybreak Circle, Clarksville, MD, United States |
| 10:00 AM - 4:00 PM | 32nd Annual In The Street - Celebrate Frederick | |
| 10:00 AM - 7:00 PM | Maryland Renaissance Festival | |
| 11:00 AM - 5:00 PM | Northern Chesapeake Wellness Fair - Aberdeen | Ripken Stadium, 873 Long Drive, Aberdeen, MD, United States |
| 11:00 AM - 5:00 PM | Northern Chesapeake Wellness Fair - Aberdeen | |
| 12:00 PM - 5:00 PM | Reid Temple AME Church Annual Community Fair - Glenn Dale | |
| 12:00 PM - 5:00 PM | Reid Temple AME Church Annual Community Fair - Glenn Dale | |
| 1:00 PM - 3:00 PM | Skipjack Nathan of Dorchester Public Sail | |