Christmas on the Square & Annual Tree Lighting

Friday, November 24, 2023
 

The holiday season begins in Leonardtown when Santa arrives for the annual Christmas Tree Lighting in the Town Square. The festivities begin at 4:30 PM with holiday music, entertainment, sleigh rides, train rides, hayrides, live nativity, balloon art, face painting, children’s crafts, hot drinks, fresh kettle korn and other fun activities including Santa's arrival to light the Tree in Leonardtown Square! For more information visit: Christmas on the Square

"Pawliday Cheer" Spa at
Earthwise Pets

Friday, December 1, 2023 at 10 a.m. - Friday, December 15, 2023 at 9 a.m.
 

Spoil your furry Best Friend with a Spa Day at the Earthwise Pets in Leonardtown Wellness Spa where they will be offering a "Pawliday Cheer" Package!

This is a Specialty Package that will be running for a limited time. Book your appointment now before the package runs out, as this is first come, first serve!

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Gingerbread House Decorating Contest at Town Market

Saturday, December 9, 2023 at 10 a.m. - Saturday, December 16, 2023 at 3 p.m.

Enter in one of two categories: Adult or Children Age 12 7 Under. Gingerbread Houses will be on display at Town Market. Judging will take place on Saturday December 16th at 2pm. Prizes will be awarded to 1st, 2nd and 3rd place, Most Creative and Most Holiday Spirit. Learn More

Holiday Movie Night at Social Feat. Bad Moms Christmas

Monday, December 11, 2023
6:30 p.m. - 9 p.m.

Enjoy a holiday movie for three Mondays in December (the 4th, 11th & 18th) at Social Coffeehouse. On Monday, December 11th, the featured movie will be Bad Moms Christmas. Enjoy an extended Happy Hour from 2 p.m. - 7 p.m. and a fun holiday movie night!

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Ugly Sweater Party & Evil Genius Tap Takeover

Saturday, December 16, 2023
Throughout the day/music starts at 8 p.m.

Join Olde Town Pub for an Ugly Sweater Party and enjoy live music from Greg Barrick and a tap takeover with Evil Genius Tap on Saturday, December 16th. Music starts at 8 p.m.
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SOF Market Christmas Open House

Sunday, December 17, 2023
11 a.m. - 3 p.m.
 

Celebrate the holidays with SOF Market. Enjoy refreshments, photos with Santa, door prizes and the dazzlers will be back to bling your holiday tresses! 

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Small Business Saturday

Saturday, November 25, 2023

Shop local, Shop Small with a wonderful collection of specialty shops and stores. You're sure to find something special for everyone on your list. For more information please contact
Jen Stotler at leonardtownmaryland@gmail.com

"Light Up Leonardtown" December First Friday

Friday, December 1, 2023
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

Fur Babies with the Grinch at Town Market

Saturday, December 9, 2023
10 a.m. - 6 p.m.
 

Bring your Fur Babies out to get their Christmas picture with the Grinch at Town Market!! Pictures are from 10am to 2pm. Check out the vendors to finish up some of your Holiday Shopping.

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Private Meet-and-Greets with Santa

Tuesday, December 12, 2023/ Saturday, December 16, 2023

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.To Register, please contact:
aris.nazarova@leonardtownmd.gov.

Wreaths & Wine at Port of Leonardtown Winery

Saturday, December 16, 2023
10 a.m. - 12 p.m.

Join Port of Leonardtown Winery for a festive evening with family and friends! Learn how to make beautiful mixed green wreaths while sampling award-winning wine.
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Holiday Movie Night at Social Feat. Elf

Monday, December 18, 2023
6:30 p.m. - 9 p.m.

Enjoy a holiday movie night at Social Coffeehouse for three Mondays in December (the 4th, 11th & 18th). On Monday, December 18th, the featured movie at Social will be Elf. Enjoy an extended Happy Hour from 2 p.m. - 7 p.m. and a fun holiday movie night!

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Polar Express Holiday Movie Night at Town Market

Friday, December 1, 2023
6:30 p.m.

Enjoy a little holiday magic with your family at the screening of the animated classic movie, The Polar Express, at Town Market (part of the Leonardtown Movie Festival) on Friday, December 1st at 6:30 p.m.
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Holiday Movie Night at Social Feat. National Lampoon's Christmas Vacation

Monday, December 4, 2023
6:30 p.m. - 9 p.m.

Enjoy a holiday movie for three Mondays in December (the 4th, 11th & 18th) at Social Coffeehouse. On Monday, December 4th, the featured movie will be National Lampoon's Christmas Vacation. Enjoy an extended Happy Hour from 2 p.m. - 7 p.m. and a fun holiday movie night!

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OTP Holiday Food Drive & Music from 
Unfinished Business

Saturday, December 9, 2023
Throughout the day/music starts at 8 p.m.
 

Olde Town Pub is collecting canned food to help those in need this holiday season throughout the day on Saturday, December 9th. All cans will be donated to local food banks and food pantries in St. Mary's County. Also, enjoy live music from Unfinished Business from 8 p.m. - 11 p.m.

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The Inn at Leonardtown Wreath Workshop

Wednesday, December 13, 2023

Learn now to make a mixed green wreath at a fun holiday workshop at the Inn at Leonardtown on Wednesday, December 13th from 6 p.m. - 7:30  p.m.
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Santa & Mrs. Claus at the Rex

Sunday, December 17, 2023
12 p.m. - 3 p.m.
 

Santa & Mrs. Claus are stopping by on their way to the North Pole to take pictures with YOU!

Awesome vendors will also be on site to help you with your Christmas shopping. 

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Jingle & Mingle
with SPICE

Friday, December 1, 2023
4 p.m. - 7 p.m.
 

Join SPICE Studio for December First Friday from 4 p.m. - 7 p.m. for their Jingle and Mingle shopping event in the SPICE Studio lobby. Shop new SPICE swag, Hometown Heart Apparel, Anchored Roots Farm, -Dixon Family Farms, and Massage at SPICE. Mulled wine will be available to purchase from Xella so you can sip while you shop!

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Salty Paintz Night at POL Winery - Snowman Door Hang

Thursday, December 7, 2023
6 p.m.
 

Bring friends or enjoy an evening with other crafters at the Port of Leonardtown Winery. Learn how to make a festive 18" snowman door hanger for your home or to give as a gift. Each ticket includes all the supplies you will need and a glass of wine or seasonal warm drink. You'll stay toasty and warm on POL's heated enclosed patio while you enjoy an
evening of holiday crafting.
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Above Par Christmas Party

Sunday, December 10, 2023
10 a.m. - 2 p.m.
 

Professional pictures with Santa, mimosa bar, craft area for gift purchasing, cookie lady, custom golf Christmas gifts available. Simulator play will be free!

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Photos with the Grinch & Holiday 
Shopping

Saturday, December 16, 2023
9 a.m. - 6 p.m.

Come out to Town Market and see the Grinch along with Max and Cindy Lou. Get your picture taken with the entire gang. Vendors will be there to help you finish your Christmas shopping as well. Learn More

The Dazzlers Event at SOF Market

Sunday, December 17, 2023
10 a.m. - 4 p.m.
 

The Dazzlers are back to help bring some bling and sparkle to your holidays on December 17th from 10 a.m. - 4 p.m. at Shepherd's Old Field Market on Duke St. behind the Firehouse.

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