| Start Date and Time | Event Details | Location |
|
| All Day | Christmas in the Woods Craft Show (Multi-Day Event) | 556 Baltimore Pike |
| All Day | 2nd Saturday Contra Dance (Multi-Day Event) | Church of Nativity & Holy Comforter Hart Hall |
| All Day | Art For the Holidays Artists' Gallery All Member Show (Multi-Day Event) | 8197 Main Street |
| All Day | Art Howard County 2019 (Multi-Day Event) | 8510 High Ridge Road |
| All Day | Artists' Boutique at Montpelier Mansion and Historic Site (Multi-Day Event) | 9650 Muirkirk Rd |
| All Day | Artists In Action - Cecil County Arts Council (Multi-Day Event) | 135 East Main Street |
| All Day | Artists in Fiction (Multi-Day Event) | 5301 Tuckerman Ln |
| All Day | Atomic Trivia - 2nd Chance Saloon (Multi-Day Event) | 5888 Rober Oliver Place |
| All Day | Atomic Trivia - Pizzaman (Multi-Day Event) | 5810 Robert Oliver Place |
| All Day | By Their Creative Force: American Women Modernists (Multi-Day Event) | 10 Art Museum Drive |
| End Day | Chestertown First Friday (Multi-Day Event) | Downtown Chestertown A&E District |
| All Day | Chestertown Second Saturday (Multi-Day Event) | 107 S Cross St |
| All Day | Christmas at the Roundhouse (Multi-Day Event) | 300 S. Burhans Blvd |
| All Day | Christmas in the Woods Craft Show (Multi-Day Event) | 556 Baltimore Pike |
| All Day | Creative Writing Workshops Strathmore Mansion (Multi-Day Event) | 5301 Tuckerman Ln |
| All Day | Cub Corner at College Park Aviation Museum (Multi-Day Event) | 1985 Corporal Frank Scott Dr |
| All Day | Distillery Tour, Whiskey & Rum Tastings, and Craft Cocktails at Old Line (Multi-Day Event) | 200 S Janney St |
| All Day | Every Day: Selections from the Collection (Multi-Day Event) | 10 Art Museum Drive |
| All Day | Exhibition: On Land and On Sea: A Century of Women in the Rosenfeld Collection (Multi-Day Event) | 213 N. Talbot St |
| All Day | Figure Drawing at Cecil County Arts Council (Multi-Day Event) | 135 East Main Street |
| End Day | First Friday Arts on the River (Multi-Day Event) | West Green Street |
| All Day | Generations: A History of Black Abstract Art (Multi-Day Event) | 10 Art Museum Drive |
| All Day | Ghost Tours of Historic Frederick - the Historic District (Multi-Day Event) | 124 North Market Street |
| All Day | Hometown Girl: Contemporary Quilts of Mimi Dietrich (Multi-Day Event) | 201 W Monument Street |
| All Day | Laugh Riot at Positano Live Standup Comedy Saturdays (Multi-Day Event) | 4948 Fairmont Ave |
| All Day | Lunchlines Poetry Group (Multi-Day Event) | 128 Karen Dr |
| All Day | Melvin Edwards: Crossroads (Multi-Day Event) | 10 Art Museum Drive |
| All Day | Miller House After Hours (Multi-Day Event) | 135 W Washington St |
| All Day | New Media: Poetry in Motion (Multi-Day Event) | 8510 High Ridge Road |
| All Day | Paul Henderson: Photographs from the Civil Rights Era (Multi-Day Event) | 1021 Dulaney Valley Rd. |
| End Day | Portrait Study at Cecil County Arts Council (Multi-Day Event) | 135 East Main Street |
| All Day | Preakness Stakes (Multi-Day Event) | Hayward & Winner Avenues |
| All Day | Prince George’s County Juried Exhibition: Reflections of Self (Multi-Day Event) | 9652 Muirkirk Rd |
| All Day | Reopening Day (Multi-Day Event) | 3 Pershing St |
| All Day | Resident Artist Open House (Multi-Day Event) | 17901 Bentley Rd |
| All Day | Seeing the Invisible: INFRARED Photography Exhibition - Walter Calahan (Multi-Day Event) | 1525 Greenspring Valley Road |
| All Day | Spencer Finch - Moon Dust (Multi-Day Event) | 10 Art Museum Dr |
| All Day | Spirits of Ellicott City Pub Crawl (Multi-Day Event) | 8390 Main Street |
| All Day | Sweet Summer (Multi-Day Event) | 3301 Annapolis Rd |
| All Day | Times of Perception Exhibition (Multi-Day Event) | 11100 Ted Herget Way |
| All Day | Tinam Valk (Multi-Day Event) | 9652 Muirkirk Rd |
| All Day | A Christmas Carol, the Musical (Multi-Day Event) | 16500 White Marsh Park Drive |
| All Day | Annmarie Ornament Show & Sale (Multi-Day Event) | 13470 Dowell Road |
| All Day | Annual Ornament Show & Sale (Multi-Day Event) | 13470 Dowell Rd |
| All Day | Christmas at the Roundhouse (Multi-Day Event) | 300 S. Burhans Blvd |
| All Day | Christmas on the Potomac Featuring ICE! (Multi-Day Event) | 201 waterfront St |
| All Day | Christmas on the Potomac Featuring ICE! (Multi-Day Event) | 201 waterfront St |
| All Day | Christmas on the Potomac Featuring ICE! (Multi-Day Event) | 201 waterfront St |
| All Day | Holiday Gift Show and Art Exhibition - RiverArts (Multi-Day Event) | 315 High Street |
| All Day | Captured Light: Current Photographic Processes (Multi-Day Event) | 12901 Town Commons Dr |
| All Day | Highlandtown Train Garden (Multi-Day Event) | Engine House # 41 |
| All Day | Irving Berlin's White Christmas: The Musical (Multi-Day Event) | 355 Ronsdale Rd |
| All Day | Macabre Yoga at Baltimore Spirits (Multi-Day Event) | 1700 W. 41st Street |
| All Day | Ocean City Winterfest of Lights (Multi-Day Event) | 125th Street, Bayside |
| All Day | Winterfest of Lights in Ocean City (Multi-Day Event) | 125th Street, Bayside |
| All Day | Garden of Lights at Brookside Gardens (Multi-Day Event) | 1800 Glenallan Ave |
| All Day | The Polar Express Train Ride (Multi-Day Event) | 13 Canal St |
| All Day | Baltimore Christmas Village (Multi-Day Event) | 501 Light Street |
| All Day | Baltimore Christmas Village (Multi-Day Event) | 501 Light Street |
| All Day | Holiday Lights Walk to the North Pole (Multi-Day Event) | 8109 Telegraph Rd |
| All Day | Holiday Lights Walk to the North Pole (Multi-Day Event) | 8109 Telegraph Rd |
| All Day | Holiday Lights Walk to the North Pole (Multi-Day Event) | 8109 Telegraph Rd |
| All Day | Miracle on 34th Street (Multi-Day Event) | 720 West 34th Street |
| All Day | Lights on the Bay (Multi-Day Event) | 1100 E College Pkwy |
| All Day | Lights on the Bay - Sandy Point State Park (Multi-Day Event) | 1100 E College Pkwy |
| All Day | Lights on the Bay - Sandy Point State Park (Multi-Day Event) | 1100 E College Pkwy |
| All Day | Mickalene Thomas: A Moment's Pleasure (Multi-Day Event) | 10 Art Museum Drive |
| All Day | Merriweather Symphony of Lights (Multi-Day Event) | 10475 Little Patuxent Pkwy |
| All Day | Festival of Wreaths - Carroll County Arts (Multi-Day Event) | Carroll Arts Center |
| All Day | Annmarie Garden In Lights (Multi-Day Event) | 13470 Dowell Road |
| All Day | Annmarie Garden In Lights (Multi-Day Event) | 13470 Dowell Rd |
| All Day | Annmarie Garden In Lights (Multi-Day Event) | 13470 Dowell Rd |
| All Day | Annmarie Garden In Lights (Multi-Day Event) | 13470 Dowell Rd |
| All Day | Beer Tastings at Christmas Village in Baltimore (Multi-Day Event) | 501 Light Street |
| All Day | Festival of Trees (Multi-Day Event) | 24 E. Church Street |
| All Day | Festival of Wreaths - Carroll County Arts (Multi-Day Event) | Carroll Arts Center |
| All Day | Fine Arts and Crafts Holiday Gift Show at Sandy Spring Museum (Multi-Day Event) | 17901 Bentley Rd |
| All Day | Holiday Train Garden & Christmas Trees at White Marsh Volunteer Fire Company (Multi-Day Event) | 10331 Philadelphia Road |
| All Day | Holiday Train Garden & Christmas Trees at White Marsh Volunteer Fire Company (Multi-Day Event) | 10331 Philadelphia Road |
| All Day | Victorian Christmas in Berlin (Multi-Day Event) | 2 North Main Street |
| All Day | Victorian Christmas in Berlin (Multi-Day Event) | 2 North Main Street |
| All Day | Highlandtown Train Garden (Multi-Day Event) | Engine House # 41 |
| All Day | Holiday Train Garden (Multi-Day Event) | 1301 York Road |
| All Day | Martinville Christmas Train and Plane Garden (Multi-Day Event) | Martin State Airport, Hangar 5 |
| All Day | Miracle on 34th Street (Multi-Day Event) | 720 West 34th Street |
| All Day | A Very Retro Christmas Exhibit at Piney Point Lighthouse Museum (Multi-Day Event) | 44720 Lighthouse Road |
| All Day | David Brosch: Recent Work by a Printmaker (Multi-Day Event) | 9652 Muirkirk Rd |
| All Day | St. Clement’s Island Museum Christmas Doll & Train Exhibit (Multi-Day Event) | 38370 Point Breeze Road |
| All Day | Candlelight Tours at Seton Shrine (Multi-Day Event) | 339 S. Seton Ave |
| All Day | Candlelight Tours at Seton Shrine (Multi-Day Event) | 339 S. Seton Ave |
| All Day | Candlelight Tours at Seton Shrine (Multi-Day Event) | 339 S. Seton Ave |
| All Day | The B&O's Magical Holiday Express (Multi-Day Event) | 901 W Pratt St |
| All Day | The B&O's Magical Holiday Express (Multi-Day Event) | 901 W Pratt St |
| All Day | Annual Community Art Show: The Best Local Art of 2019 (Multi-Day Event) | 34 S. Potomac St, Suite 100 |
| All Day | Annual Community Art Show: The Best Local Art of the Year (Multi-Day Event) | 34 S. Potomac St, Suite 100 |
| All Day | Easton Choral Arts Society presents Christmas by Candlelight (Multi-Day Event) | 111 So. Harrison St |
| All Day | Holiday Gifts & Greens Sale - Frederick (Multi-Day Event) | 106 W. Church St. |
| All Day | Holiday Midnight Madness Shopping In Annapolis (Multi-Day Event) | Downtown Annapolis |
| All Day | MICA Art Market (Multi-Day Event) | 1300 W Mount Royal Ave |
| All Day | The Best Christmas Pageant Ever (Multi-Day Event) | 108 East Street |
| 3rd Annual Pack-a-Trolley to Benefit Comfort Cases | 550 Light St |
| 3rd Annual Pack-a-Trolley to Benefit Comfort Cases | 550 Light St |
| Start Day | A Christmas Carol at Chesapeake Shakespeare Company (Multi-Day Event) | 7 South Calvert Street |
| Start Day | A Great Small Town Christmas (Multi-Day Event) | Downtown Oakland |
| A John Denver Christmas with Chris Collins and Boulder Canyon | 20 W Patrick St |
| 12:00 AM - Midnight | Annual Christmas Open House at Ladew Gardens | 3535 Jarrettsville Pike |
| Anthony Walker & Friends: A Christmas Celebration | 11810 Grand Park Avenue |
| 12:00 AM - Midnight | Christmas in the Village at Spruce Forest | 177 Casselman Rd |
| Start Day | Dickens of a Christmas (Multi-Day Event) | High and Cross Streets |
| Start Day | Door to Bethlehem Tour at Seton Shrine (Multi-Day Event) | 339 S. Seton Ave |
| Start Day | Door to Bethlehem Tour at Seton Shrine (Multi-Day Event) | 339 S. Seton Ave |
| 12:00 AM - Midnight | Garrett County Christmas Tour of Homes | 12982 Garrett Highway |
| History Happy Hour: Code Girls | 17901 Bentley Road |
| 12:00 AM - Midnight | Holiday Bazaar and Cookie Walk | 2515 Churchville Rd |
| 12:00 AM - Midnight | Holiday Bazaar and Cookie Walk | 2515 Churchville Rd |
| Start Day | Holiday Candlelight Stroll - Annapolis (Multi-Day Event) | 1 Dock Street |
| Start Day | Holiday Candlelight Stroll - Annapolis (Multi-Day Event) | 1 Dock Street |
| Holidays of Light and Love with the Choral Arts Society of Frederick | 7932 Opossumtown Pike |
| 12:00 AM - Midnight | Krampus A Haunted Christmas presented by Bennett's Curse Haunted House | 7875 Eastpoint Mall Baltimore, MD 21224, 7875 Eastpoint Mall |
| Midnight Madness in Historic Ellicott City | 8267 Main Street |
| Start Day | Muddy Creek Artists Guild Holiday Art Show and Sale (Multi-Day Event) | 179 Mitchells Chance Rd |
| Paula Poundstone | 33 West St |
| Paula Poundstone (9:30pm Show) | 33 West St. |
| Pinkham, Poulenc, and Chopin | 1 E Mount Vernon Pl |
| PLATINUM MOVIE: Green Book (2018) | 5445 Landover Rd |
| PLATINUM MOVIE: Green Book (2018) | 5445 Landover Rd |
| Santa Chase - Note New Date and Time | 137 Deep Shore Rd |
| The Lettermen Live Oldies & Holiday Show | 533 Riverside Dr. |
| Start Day | The Nutcracker - Eastern Shore Ballet Theatre (Multi-Day Event) | 201 Long Ave |
| Ugly Christmas Sweater Party at Layton's Chance | 4225 New Bridge Rd. |
| 10:00 AM - 1:00 PM | Baltimore City | |
| 1:00 PM - 5:00 PM | 1st Workforce Resource Fair for the African Community in Maryland - Bowie | |