| Start Date and Time | Event Details | Location |
|
| End 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 |
| 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 |
| End 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 | 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. |
| 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 | 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 | 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 |
| End 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 |
| End 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 |
| End Day | Easton Choral Arts Society presents Christmas by Candlelight (Multi-Day Event) | 111 So. Harrison St |
| All Day | Holiday Midnight Madness Shopping In Annapolis (Multi-Day Event) | Downtown Annapolis |
| End 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 |
| All Day | A Christmas Carol at Chesapeake Shakespeare Company (Multi-Day Event) | 7 South Calvert Street |
| All Day | A Great Small Town Christmas (Multi-Day Event) | Downtown Oakland |
| End Day | Dickens of a Christmas (Multi-Day Event) | High and Cross Streets |
| End Day | Door to Bethlehem Tour at Seton Shrine (Multi-Day Event) | 339 S. Seton Ave |
| End Day | Door to Bethlehem Tour at Seton Shrine (Multi-Day Event) | 339 S. Seton Ave |
| All Day | Holiday Candlelight Stroll - Annapolis (Multi-Day Event) | 1 Dock Street |
| All Day | Holiday Candlelight Stroll - Annapolis (Multi-Day Event) | 1 Dock Street |
| All Day | Muddy Creek Artists Guild Holiday Art Show and Sale (Multi-Day Event) | 179 Mitchells Chance Rd |
| End Day | The Nutcracker - Eastern Shore Ballet Theatre (Multi-Day Event) | 201 Long Ave |
| All Day | A Stitch to Wear: Wearable Art Competition & Exhibition (Multi-Day Event) | 9 N. Centre Street |
| All Day | December Saturdays in Downtown Frederick (Multi-Day Event) | Downtown Frederick |
| All Day | December Saturdays in Downtown Frederick (Multi-Day Event) | Downtown Frederick |
| All Day | Family Workshop: Create Buttermold Ornaments (Multi-Day Event) | 135 W. Washington St. |
| All Day | Festival of Trains with Queen Anne's Railroad Society (Multi-Day Event) | 61 Piney Narrows Road |
| All Day | Metropolitan Ballet Theatre's Annual Production of The Nutcracker (Multi-Day Event) | 51 Mannakee Street |
| All Day | Santa's Magic Workshop (Multi-Day Event) | 137 Deep Shore Rd |
| All Day | The Wiz (Multi-Day Event) | 2600 N. Howard Street |
| A Nutcracker Tea | 4 Frederick Road |
| Annapolis Chocolate Binge Festival | 55 West Street |
| Columbia Pro Cantare: Handel's Messiah | 5460 Trumpeter Rd |
| Family Art Frenzy - December | 6100 Foreland Garth |
| Family Holiday Party at the Sandy Spring Museum | 17901 Bentley Rd |
| Handel's Messiah with Bach in Baltimore City | 2800 O'Donnell Street |
| Heidi Newfield formerly of Trick Pony | 33 West St. |
| Instagram Ready Art: Mini Sculpey Figurines - December | 6100 Foreland Garth |
| Mayor's Christmas Parade | 832 W. 36 St |
| Metropolitan Ballet Theatre's The Nutcracker Suite, Sensory-friendly performance | 51 Mannakee Street |
| Mid-Atlantic Symphony "Holiday Joy: A Salute to the Music of the Big Band Orchestras" | 4001 Coastal Hwy Ocean City |
| Old Tyme Holiday Gathering | 305 Queen Anne Street |
| Olde Tyme Holiday Gathering in La Plata | 305 Queen Anne Street |
| Public Reception - David Brosch: Recent Work by a Printmaker | 9652 Muirkirk Rd |
| SQRRL! Family Holiday Show | 33 West St |
| The Sweetback Sisters | 11810 Grand Park Avenue |
| Winter Handbell Concert | 1601 Washington Road |
| WINTER WONDERYESAND: Improv Comedy Show | 1727 N Charles St |
| 9:00 AM - 4:00 PM | East Coast Indoor Nationals Car, Truck and Bike Show - Timonium | |