| Start Date and Time | Event Details | Location |
|
| End Day | Exhibition: Marilyn Holsing/Les Histoires (Multi-Day Event) | Towson University Center for the Arts MFA Gallery, CA 2040 |
| End Day | Reference/Material Exhibition (Multi-Day Event) | Towson University Center for the Arts, Holtzman MFA Gallery, CA 2040 |
| All Day | Autumn Glory Festival (Multi-Day Event) | Garrett County, Maryland |
| All Day | Autumn Glory Festival (Multi-Day Event) | Main St. |
| All Day | Fair Hill International (Multi-Day Event) | 489 Gallaher Rd |
| All Day | Fall Maryland Home & Garden Show (Multi-Day Event) | Maryland State Fairgrounds |
| All Day | Sugarloaf Crafts Festival in Gaithersburg (Multi-Day Event) | 16 Chestnut Street |
| All Day | United States Powerboat Show (Multi-Day Event) | One Dock Street |
| All Day | Regional Planning Conference (Multi-Day Event) | |
| 11th Annual Fall International Wine Tasting | St. Stephen Kingsville |
| 12:00 AM - Midnight | 19th Annual Bethesda Row Arts Festival | 7115 Arlington Road Bethesda Ave |
| ACLT Guided Canoe Trip on Parker Creek | 676 Double Oak Rd. |
| 12:00 AM - Midnight | Air Show Baltimore | Inner Harbor, Fells Points, Canton, MedStar Harbor Hospital |
| 12:00 AM - Midnight | Art @ the Park 2016 | 600 Quiet Waters Park Road |
| 12:00 AM - Midnight | Autumn Wine Festival | 5561 Plantation Ln |
| 12:00 AM - Midnight | Bethesda Row Arts Festival | Woodmont and Bethesda Avenues, Bethesda Lane, and Elm Street |
| Bowie State University Homecoming 2016: Legacy Parade | Parade will begin at Ruby Tuesday's and end at Bowie Town Center Macy's |
| Bowie State University Homecoming 2016: Legacy Parade | Parade begins at Ruby Tuesday's and end at Bowie Town Center Macy's |
| Carroll Live On Stage Presents Alina Kiryayeva | Westminster High School |
| Charles County Wine & Food Festival | 11765 St. Linus Drive, Waldorf, MD |
| Cheers for Charity Wine Tasting Fundraiser | Dawson's Market |
| David Sedaris | 20 W Patrick St |
| Fairy House Workshop | 300 Oella Ave |
| Great Pumpkin Adventure | 8600 Foundry St |
| Great Pumpkin Adventure | 8600 Foundry St |
| Harford Plein Air Public Gallery Sale & Reception | Liriodendron Mansion |
| Harford Plein Air Public Gallery Sale & Reception | Liriodendron Mansion |
| Laurel History Boys! | 9650 Muirkirk Rd |
| Martin State Airport Open House | Martin State Airport |
| Octoberfest | Downtown Main Street |
| Phil Vassar | 33 West St. |
| Phil Vassar | 33 West St. |
| Quick Draw Competition at Harford Plein Air | Bel Air Farmers' Market |
| Quick Draw Competition at Harford Plein Air | Bel Air Farmers' Market |
| Tea with the Dearly Departed | 9650 Muirkirk Rd |
| The Darker Side of Historic St. Mary's City | Rt 5 and Rosecroft Rd |
| The Walters Party 2016: A Medieval Revelry | 600 N Charles St |
| Tilghman Island Day | US 322 to Rt 33 |
| 12:00 AM - Midnight | U.S. Oyster Festival in St. Mary's County | 42455 Fairgrounds Road |
| 12:00 AM - Midnight | U.S. Oyster Festival in St. Mary's County | 42455 Fairgrounds Road |
| 8:00 AM - 1:00 PM | Oxon Hill High School: Career Fair | |
| 8:30 AM - 1:00 PM | Congresswoman Donna Edwards - 8th Annual College & Career Fair | |
| 10:00 AM - 3:00 PM | 7th Annual Calvert Hall Car and Craft Show to benefit the Instrumental Music Program | |
| 10:00 AM - 4:00 PM | 8th Annual Cockeysville Fall Festival | |
| 10:00 AM - 2:00 PM | Community Marketplace @ Shabach! - Hyattsville | |
| 10:00 AM - 9:00 PM | Maryland Home & Garden Show - Timonium | |
| 10:00 AM - 2:00 PM | Montgomery County Transitioning Youth Resource Fair - Takoma Park | |
| 11:00 AM - 2:00 PM | Disability Awareness Day 2016 - Annapolis | |
| 11:00 AM - 12:00 PM | Ocean Pines Fire Department: Open House | |