| 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 |
| 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 |
| End Day | Figure Drawing at Cecil County Arts Council (Multi-Day Event) | 135 East Main 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. |
| 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 |
| End 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 |
| End 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 |
| End 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 |
| 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 |
| All Day | Dickens of a Christmas (Multi-Day Event) | High and Cross Streets |
| All Day | Door to Bethlehem Tour at Seton Shrine (Multi-Day Event) | 339 S. Seton Ave |
| All 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 |
| All Day | The Nutcracker - Eastern Shore Ballet Theatre (Multi-Day Event) | 201 Long Ave |
| Start Day | A Stitch to Wear: Wearable Art Competition & Exhibition (Multi-Day Event) | 9 N. Centre Street |
| ACLT's Annual Wreath and Greens Sale | 2650 Scientists Cliff Road |
| Bethesda's Winter Wonderland | Corner of Norfolk and Woodmont Avenues |
| 12:00 AM - Midnight | BSO Presents Handel Messiah | 1212 Cathedral Street |
| Cambridge-Dorchester County Parade | High Street |
| 12:00 AM - Midnight | Candlelight House Tour - Historic Frederick | William R. Talley Recreation Center |
| 12:00 AM - Midnight | Candlelight House Tour - Historic Frederick | William R. Talley Recreation Center |
| Cecil County Christmas Parade | Main Street |
| Celtic Christmas Concert featuring Charlie Zahm & Friends | 201 Mt. Royal Ave |
| 12:00 AM - Midnight | Charles County Holiday Trail | Various museums and Historic sites |
| Charm City Craft Mafia - Holiday Heap | 2640 St Paul Street |
| Christmas Craft Show - Harford Vineyard & Winery | 1311 W. Jarrettsville Rd. |
| Christmas in Crisfield | 1012 West Main Street |
| Christmas on the (North) Beach Holiday Parade, Holiday Market and Santa | 9023 Bay Avenue |
| Colonial Christmas | 47414 Old State House Road |
| Colonial Christmas at Historic St. Mary's City | Rt 5 and Rosecroft Rd |
| Columbia Orchestra: American Stories | 5460 Trumpeter Rd |
| Start Day | December Saturdays in Downtown Frederick (Multi-Day Event) | Downtown Frederick |
| Start Day | December Saturdays in Downtown Frederick (Multi-Day Event) | Downtown Frederick |
| Family Fun Series: Holidays Around the World | 5445 Landover Rd |
| Family Fun Series: Holidays Around the World | 5445 Landover Rd |
| Start Day | Family Workshop: Create Buttermold Ornaments (Multi-Day Event) | 135 W. Washington St. |
| Start Day | Festival of Trains with Queen Anne's Railroad Society (Multi-Day Event) | 61 Piney Narrows Road |
| Fused Glass Square Bowl Sampling Workshop - December 7 | 6100 Foreland Garth |
| 12:00 AM - Midnight | German American Weekend at Christmas Village in Baltimore | 501 Light Street |
| Handel's Messiah - Bach in Baltimore Goes to Ellicott City | 3604 Chatham Road |
| Holiday Film Series: The Star | 339 South Seton Avenue |
| Holiday Horse Open House | 25410 Rosedale Manor Lane |
| Holiday Parade and Christmas on the Beach | Bay Avenue |
| Holiday Purse Bingo | 25 Church Street |
| Holidays on the Farm | 1611 N. Market St. |
| Holidays on the Farm | 1611 N. Market St. |
| Start Day | Metropolitan Ballet Theatre's Annual Production of The Nutcracker (Multi-Day Event) | 51 Mannakee Street |
| Natural Holiday Sale - Howard County Conservancy | 10520 Old Frederick Rd |
| Navy Men's Basketball vs. Marist | 675 Decatur Rd |
| Ocean City Christmas Parade | 12000 Coastal Hwy |
| Poplar Hall Christmas Market in Chesapeake City | Pell Gardens |
| Salisbury Symphony Orchestra Presents Horn for the Holidays | 1101 Camden Avenue |
| 12:00 AM - Midnight | Santa's Farm Fest | 10102 Fingerboard Road |
| Start Day | Santa's Magic Workshop (Multi-Day Event) | 137 Deep Shore Rd |
| Short Film Slam: Round V Championships presented by The Madlab Post | 120 North Avenue |
| Solomons Christmas Walk | Throughout Solomons |
| Super Secret Elf Workshop | 40 S Carroll St |
| The Oak Ridge Boys Christmas Celebration | 4001 Coastal Highway |
| The Oak Ridge Boys Christmas Celebration in Ocean City | 4001 Coastal Highway |
| Start Day | The Wiz (Multi-Day Event) | 2600 N. Howard Street |
| 9:00 AM - 3:00 PM | Charles County - Last Chance Enrollment Event (Waldorf) | |
| 9:00 AM - 7:00 PM | East Coast Indoor Nationals Car, Truck and Bike Show - Timonium | |
| 9:00 AM - 1:00 PM | Montgomery County | |
| 9:00 AM - 3:00 PM | Montgomery County - Last Chance Enrollment Event (Germantown) | |
| 9:30 AM - 2:30 PM | Calvert County - Last Chance Enrollment Event (Solomons) | |
| 9:30 AM - 12:30 PM | Talbot County - Last Chance Enrollment Event (Easton) | |
| 10:00 AM - 2:00 PM | Prince George's County - Last Chance Enrollment Event (Landover) | |
| 10:30 AM - 4:00 PM | Harford County - Last Chance Enrollment Event (Bel Air) | |