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| Start Date and Time | Event Details | Location |
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| All Day | "Off the Beaten Path" - Photos by Debbi Granruth (Multi-Day Event) | The Liriodendron Foundation Gallery |
| All Day | A Great Small Town Christmas and Winter Fest (Multi-Day Event) | Downtown Oakland |
| All Day | Annual Christmas Open House at Ladew Gardens "The Colors of Christmas" (Multi-Day Event) | 3535 Jarrettsville Pike |
| All Day | Charles County Holiday Trail (Multi-Day Event) | Various Locations |
| All Day | Christmas in St. Michaels (Multi-Day Event) | 200 S. Talbot Street |
| All Day | Festival of Trains (Multi-Day Event) | Kent Narrows Outlet Stores |
| All Day | Gingerbread House Contest and Show (Multi-Day Event) | Darnall's Chance House Museum |
| All Day | Gingerbread House Contest and Show (Multi-Day Event) | Darnall's Chance House Museum |
| All Day | Marvel Universe Live! (Multi-Day Event) | Royal Farms Arena |
| All Day | Maryland Regional Ballet presents The Nutcracker-Weinberg Center (Multi-Day Event) | 20 W Patrick St |
| All Day | Old Fashion Christmas Sudlersville Train Museum (Multi-Day Event) | Sudlersville |
| All Day | The Full Story: Maryland, The Surratts, and the Crime of the Century (Multi-Day Event) | 9118 Brandywine Rd |
| All Day | 'Tis the Season with Brian Stokes Mitchell (Multi-Day Event) | 1212 Cathedral Street |
| $10,000 Giving Tree | 198 Laurel Race Track Rd |
| 9th Annual Christmas Market | 5961 Sunderleigh Drive |
| Annapolis Opera presents Angels & Demons: A Concert | Bowie Center for the Performing Arts |
| Arts by the Bay Candlelight Tour | Arts by the Bay Gallery |
| Bethesda Big Train Toy Drive | 10600 Westlake Drive |
| Breakfast with Santa | 18751 Hogaboom Lane |
| Breakfast with Santa | Chapel of the Incarnation |
| Calvert Artists' Guild December Meeting | Asbury Solomons ClubHouse |
| Candlelight Tour of Havre de Grace | Susquehanna Museum |
| Charm City Craft Mafia - Holiday Heap | 2640 St Paul Street |
| 12:00 AM - Midnight | Christmas in St. Michaels | |
| Christmas Luncheon with Santa Claus | Inner Harbor Promenade |
| Eastport Yacht Club Lights Parade | Eastport Yacht Club |
| Family Plantation Christmas | 44300 Sotterley Ln |
| Frederick Foote Book Signing Event Benefits Wounded Warriors | 814 N Collington Ave. |
| 12:00 AM - Midnight | Holiday Boutique | Susquehanna Museum |
| 12:00 AM - Midnight | Holiday Spectacular | Mercy High School |
| Holiday Wreath and Garland Class | 10568 Cliff Road |
| Holiday Wreath and Garland Class | 10568 Cliff Road |
| 12:00 AM - Midnight | Holidays at Hampton | 535 Hampton Ln |
| Hometown Holidays | Brunswick, City of |
| Lisbon Ole Fashion Christmas Parade | 7523 John Pickett Road |
| Mrs. Cratchit’s Tea Parlour | 807 Elk Mills Rd, Elkton, MD 21921 |
| Natural Ornaments | 300 Oella Ave |
| Soaring with Santa | 8600 Foundry St |
| Sock Monkey Saturday | Baltimore Inner Harbor |
| 12:00 AM - Midnight | The Baltimore Ballet presents: The Nutcracker | 1021 Dulaney Valley Road |
| The Humbug Pub Dinner | 807 Elk Mills Rd |
| 9:30 AM - 1:30 PM | Take Charge of Your Health, Cancer Survivorship Forum - Baltimore | Zeta Center, 4501 Reisterstown Road, Baltimore, MD |
| 10:00 AM - 12:30 PM | Suitland High School's Community Family Market and Resource Day | 5200 Silver Hill Road District Heights, MD (Media Center) |
| 10:00 AM | Wreaths Across America | |
| 10:00 AM | Wreaths Across America | |
| 11:00 AM - 4:00 PM | Shoppers Food Warehouse Consumer Outreach - Laurel | 13600 Baltimore Avenue, #100 Laurel, MD |
| 11:00 AM - 4:00 PM | Shoppers Food Warehouse Consumer Outreach - New Carrollton | 7790 Riverdale Road New Carrollton, MD |
| 11:00 AM - 4:00 PM | Shoppers Food Warehouse Consumer Outreach - Takoma Park | 6881 New Hampshire Avenue Takoma Park, MD |
| 11:30 AM | Wreaths Across America | |
| 12:00 PM | Wreaths Across America | |
| 12:00 PM | Wreaths Across America | |
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