Holiday Fun in St. Mary's

Catch the glow! St. Mary's is filled with warmth and holiday cheer this holiday season!

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Festive Leonardtown

Historic Leonardtown, in the heart of St. Mary's, greets the holiday season with great shopping, dining, and cool events

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History Buff Holidays

St. Mary's County has some great things to do during the holiday season for history enthusiasts. 

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Shop Local, Shop Leonardtown

Centrally located, Leonardtown serves as a convenient hub. Celebrate the season and shop the neighborhood!

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Award Winning Wines

Sample some really fine wine at our wineries. But it’s not only the wines that are full of character! Located on the Patuxent Wine Trail, our wineries are sure to please.

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So. Maryland, So Good Holiday Guide

Check out this list of farms and other farm-related businesses in Southern Maryland that feature events and products throughout the late fall, winter and holiday season. 

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Watch a video introduction to St. Mary's County and view other videos.

Don't Miss…

Upcoming Events

Open Barn at Greenwell State Park

Every Saturday morning, meet with Greenwell's horses, watch riding lessons, and learn about the Greenwell Foundation's equestrian programs. FREE.

Vintage Source Weekend

The Vintage Source resides in an old general store and is only open on the third… more

Holiday Horse Photo Op

Join the Greenwell Foundation for some holiday fun. Pony rides, take photos with the horses and… more

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Santa & Mrs. Claus on the Square

Bring your camera and wish list for a special visit with Santa and Mrs. Claus in historic Downtown Leonardtown.

Vintage Source Weekend

The Vintage Source resides in an old general store and is only open on the third… more

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Show at Opal Fine Art Gallery

Enjoy great themed gallery shows each month from the wonderful artists at Opal Fine Art Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

Open Barn at Greenwell State Park

Every Saturday morning, meet with Greenwell's horses, watch riding lessons, and learn about the Greenwell Foundation's equestrian programs. FREE.

Gallery Shows at North End Gallery

Enjoy great themed gallery shows each month from the incredible artists at North End Gallery in Leonardtown.

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