| Start Date and Time | Event Details | Location |
|
| All Day | Academy Art Museum Craft Show (Multi-Day Event) | |
| All Day | Annual Amazing Corn-Maze (Multi-Day Event) | |
| All Day | Baltimore Beer Week (Multi-Day Event) | |
| All Day | Fair Hill International Festival in the Country (Multi-Day Event) | |
| All Day | Sugarloaf Crafts Festival in Gaithersburg (Multi-Day Event) | |
| All Day | U.S. Powerboat Show, 43rd Annual (Multi-Day Event) | |
| Start Day | Antique and Classic Car Show (Multi-Day Event) | |
| All Day | Baltimore Running Festival | |
| All Day | Battlefield Hikes at Monocacy National Battlefield | |
| Start Day | Calvert County Farm Festival (Multi-Day Event) | |
| Start Day | Fall Harvest Days (Multi-Day Event) | |
| All Day | Maryland Million | |
| Start Day | Native American Heritage Festival & Pow Wow (Multi-Day Event) | |
| Start Day | Oyster Festival (Multi-Day Event) | |
| All Day | Roads and What They Were Made Of | |
| All Day | Sailwinds Park East Kite Festival | |
| All Day | The 8th Annual Island Bay Day | |
| 7:00 AM - 3:00 PM | 7th Annual Frederick Community Health Fair | 797 East Patrick Street Frederick, MD (Frederick County Fairgrounds) |
| 7:00 AM - 11:30 AM | Maryland State Education Association Conference: Apple-A-Day Health Fair - Ocean City | 4001 Coastal Highway Ocean City, MD (Roland E. Powell Convention Center) |
| 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 - 8:00 PM | Maryland Home & Garden Show - Timonium | Maryland State Fairgrounds, Cow Palace, Timonium, MD |
| 9:00 AM - 1:30 PM | Transitioning Youth Resource Fair - Takoma Park | |
| 9:00 AM - 5:00 PM | Wealth Diversity Summit | |
| 10:00 AM - 3:00 PM | 2014 Family Time Expo - Waldorf | Capital Clubhouse, 3033 Waldorf Market Place, Waldorf, MD, United States |
| 10:00 AM - 6:00 PM | Fall Business Expo | Harford County |
| 10:00 AM - 7:00 PM | Maryland Renaissance Festival | |
| 11:00 AM | Fell's Point Heritage Trail Tour | |
| 11:00 AM - 3:00 PM | Touch-A-Truck - Glen Burnie | |
| 1:00 PM - 3:00 PM | Skipjack Nathan of Dorchester Public Sail | |