Leonardtown: A Most Convenient Place

Centrally located, Leonardtown serves as a convenient hub for shopping, dining & more.

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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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Maryland Distillers Showcase

Join the Maryland Distillers Guild at the Patuxent River Naval Air Museum & Visitors Center on February 11 for an afternoon of Southern Maryland heritage and tasting of great Maryland-made spirits.

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Greenwell State Park

The Cool Outdoors

For those outdoor types who love the cold weather, we've got lots for them to do.

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Terrific Trails

Whether its deep-into-Nature hiking trails or “Howdy, neighbor,” walking trails, St. Mary's has the pathway for your particular style.

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Island Weekend

Beautiful St. George Island is the perfect location for a weekend island getaway!

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

Don't Miss…

Upcoming Events

Vintage Source Weekend

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

Music at the Winery

Chill with the live tunes of local artists at the winery each Saturday while sipping on award winning wines.

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.

Appraiser’s Fair 2017

Determine the value of your prized possessions! Appraisers for jewelry, furniture, glassware, pottery, artwork, music boxes… 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 Show at Opal Fine Art Gallery

Enjoy great themed gallery and group 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 Show at Opal Fine Art Gallery

Enjoy great themed gallery and group 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 Show at Opal Fine Art Gallery

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

Leonardtown First Fridays

The First Friday of each month, historic Leonardtown retailers open their doors to showcase live music,… more

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.

Gallery Show at Opal Fine Art Gallery

Enjoy great themed gallery and group 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.

Gallery Show at Opal Fine Art Gallery

Enjoy great themed gallery and group 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 Show at Opal Fine Art Gallery

Enjoy great themed gallery and group 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 Show at Opal Fine Art Gallery

Enjoy great themed gallery and group shows each month from the wonderful artists at Opal Fine Art 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.

Gallery Show at Opal Fine Art Gallery

Enjoy great themed gallery and group 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.

Gallery Show at Opal Fine Art Gallery

Enjoy great themed gallery and group 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 Show at Opal Fine Art Gallery

Enjoy great themed gallery and group 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 Show at Opal Fine Art Gallery

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

Vintage Source Weekend

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

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.

Gallery Show at Opal Fine Art Gallery

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

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