North End Gallery 36th Annual Holiday Show

November 22 -
December 31, 2022
11 a.m. - 5 p.m. daily

North End Gallery Members have been busy this entire year prepping for this exciting annual holiday show. Stop by and browse and shop the creations of local member artists. The gallery is open daily from 11 a.m. - 5 p.m. from November 22nd - December 31st.  For more information visit: northendgallery.com.

Fur Babies with the Grinch

Saturday, December 10, 2022
10 a.m. - 1 p.m.

Bring your Fur Babies out to Town Market, located under the covered area next to the old Bell Motor Company Building on Washington Street, on Saturday, December 10th between 10 a.m. - 1 p.m. to get their Christmas picture with the Grinch!! Vendor opportunities are currently available for this event. For more information to apply or regarding the event go to: (15) Fur Babies Picture with the Grinch | Facebook

Earthwise Pet in Leonardtown Holiday Party

Saturday, December 17, 2022
10 a.m. - 4 p.m.

Join Earthwise in celebrating the most wonderful time of the year! Fur friends can enjoy specialty treats from Furtastic Barkery! There will be giftable items on sale, and pictures with the Grinch! for more information visit: https://www.facebook.com/earthwisepetleonardtown

"Light Up Leonardtown" December First Friday

Friday, December 2, 2022
5 p.m. - 8 p.m.

Join us on First Friday for a wonderful day of exploring Leonardtown: Shop, Dine, Explore and more! See Leonardtown decked out in its holiday finest for the season. For more information and to view the First Friday Itinerary visit: Leonardtown First Friday

Private Meet-and-Greets with Santa

Tuesday, December 13, 2022 / Saturday, December 17, 2022
BOTH EVENTS ARE FULL/
WAIT LIST ONLY

Private Meet-and-Greets with Santa are held for families with loved ones with disabilities & for families celebrating a baby's 1st Christmas. These private meetings are a magical experience for families who usually are unable to bring their loved ones to meet Santa in settings with long lines and crowds.
REGISTRATION IS NOW FULL:

If you would like to be placed on the waiting list in the event of an opening, please email:
 brandy.blackstone@leonardtownmd.gov.

Photos with the Grinch

Saturday, December 17, 2022
5 p.m.
 

Come out and see the Grinch along with Max and Cindy Lou. Get your picture taken with the entire gang. Free raffle for Children's Basket that has some great stuff. Vendors are here to help you finish your Christmas shopping as well. Vendor spots are currently still available. For details on how to apply or for more information about the event visit: (15) Come Out and See the Grinch!! | Facebook

Pjammin with Santa

Saturday, December 3, 2022
1 p.m. - 4 p.m.
 

Wear your favorite holiday pajamas for family photos with Santa at Above Par Golf & Entertainment! Sto by anytime during 1:00-4:00pm on Saturday, December 3rd. Above Par will also have a Putting and Closest to the Pin contests as well! Donations during this event will support the Amercian Childhood Cancer Organization.

Thrift Store Santa

Friday, December 16, 2022
6:30 p.m. - 8 p.m.
 

Wear your ugliest holiday sweater and save a Santa from the landfill! Join us in the studio for a night of painting fun using our collection of all sorts of Santas. You get to make a painting and take a Santa home with you! For more information visit: (16) Thrift Store Santa Party | Facebook

SOF Christmas Open House

Sunday, December 18, 2022
11 a.m. - 5 p.m.
Shop from over 90 small businesses, enjoy refreshments, a gift-wrapping station and entertainment. Shepherd's Old Field Market.

Mr. Grinch Cookie Class 

Thursday, December 8, 2022
5 p.m. - 7:30 p.m.
 

In this sweet workshop you will learn techniques and skills to decorating Sugar cookies!! Come learn how to level up your cookie decorating skills with insider secrets to professional cookie decorating from Hi Sugar Bakery. With this hands-on demonstration class, you will get to learn, decorate, and EAT your very own cookie art creations! This event takes places at the beautiful Fenwick Inn on Fenwick Street.

For more information visit: (14) Mr. Grinch Cookie Class with Hi Sugar | Facebook.

Santa & Mrs. Claus on the Square

Saturday, December 17, 2022
11 a.m. - 1 p.m.
 

Bring your wish lists and your cameras for a visit with Santa and Mrs. Claus! This event is FREE and open to the public (no reservations are needed).
 

This event will be held rain or shine inside Ye Olde Towne Cafe (located at: 22685 Washington St, Leonardtown, MD 20650).  The restaurant will also be open for anyone who wishes to dine before or after their photos with the jolly old elf and his lovely wife.
 

For more information contact: brandy.blackstone@leonardtownmd.gov or 301-475-9791.

Christmas Cookies for Santa

Thursday, December 20, 2022
5:30 p.m. - 7:30 p.m.
In this sweet workshop you will learn techniques and skills to decorating Sugar cookies!! Come learn how to level up your cookie decorating skills with insider secrets to professional cookie decorating from Hi Sugar Bakery. With this hands-on demonstration class, you will get to learn, decorate, and EAT your very own cookie art creations!
For more information and to register visit: (14) Christmas Cookies for Santa Class | Facebook