| Start Date and Time | Event Details | Location |
|
| All Day | Art For the Holidays Artists' Gallery All Member Show (Multi-Day Event) | 8197 Main Street |
| 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 - 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 | Christmas at the Roundhouse (Multi-Day Event) | 300 S. Burhans Blvd |
| 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 | 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 | Spencer Finch - Moon Dust (Multi-Day Event) | 10 Art Museum Dr |
| 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 | 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 |
| End 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 | 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 | 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 | 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 |
| End 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 | 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 | A Christmas Carol at Chesapeake Shakespeare Company (Multi-Day Event) | 7 South Calvert Street |
| End Day | Holiday Candlelight Stroll - Annapolis (Multi-Day Event) | 1 Dock Street |
| End Day | Holiday Candlelight Stroll - Annapolis (Multi-Day Event) | 1 Dock Street |
| All Day | A Stitch to Wear: Wearable Art Competition & Exhibition (Multi-Day Event) | 9 N. Centre Street |
| End Day | December Saturdays in Downtown Frederick (Multi-Day Event) | Downtown Frederick |
| End 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 | The Wiz (Multi-Day Event) | 2600 N. Howard Street |
| All Day | Holiday Tours at Montpelier (Multi-Day Event) | 9650 Muirkirk Rd |
| All Day | Adorned: African Women and the Art of Identity (Multi-Day Event) | 10 Art Museum Dr |
| All Day | Adorned: African Women and the Art of Identity for the Year of the Woman (Multi-Day Event) | 10 Art Museum Dr |
| All Day | Adorned: African Women and the Art of Identity for the Year of the Woman (Multi-Day Event) | 10 Art Museum Dr |
| All Day | Free Form: 20th-century Studio Craft (Multi-Day Event) | 10 Art Museum Drive |
| All Day | Free Form: 20th-Century Studio Craft (Multi-Day Event) | 10 Art Museum Drive |
| All Day | A Christmas Carol (Multi-Day Event) | 20 W. Patrick St. |
| Danny Burns w/ special guest Aine O'Doherty | 33 West St. |
| Engineering 101 - Gliders | 1985 Corporal Frank Scott Dr |
| Family Holiday Concert at the Jim Rouse Theatre | 5460 Trumpeter Road |
| Ho, Ho, Ho... Santa Claus Comes to the Art to Soul Galleria Part Two | 2101 Belair Road |
| Holiday Film Series: Classic Christmas Specials | 339 South Seton Avenue |
| Holidays in Black & White - The American Pops Orchestra | 311 Kent Square Road |
| 12:00 AM - Midnight | Home for the Holidays Concert | 21-27 S Potomac St |
| Perry Hall Folk Music Night, featuring Evan Alexander Moore | 9515 Belair Rd. |
| Santa & Mrs. Claus on the Square in Leonardtown | 22670 Washington Street |
| Slim Man CD Release Party | 33 West St |
| Soul Crackers Annual Holiday Show | 11810 Grand Park Avenue |
| Sugar Plum Tea Party with Metropolitan Ballet Theatre | 220 Perry Parkway, Suite 8 |
| Winter Holiday Market at the Ocean Pines Farmers & Artisans Market | 239 Ocean Parkway |
| 1:00 PM - 4:00 PM | Montgomery County | |
