7 Best Paint & Wine Spots in Maryland 2025!

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Wine & Design, Leonardtown, MD

Wine & Design did not start because of this fun national trend. Instead, local artists, wine lovers, and the community decided to come together to have a good time. Local artists are on hand, paint… Read More

The 9 Best Mexican Restaurants in Maryland!

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Salsa Mexican Café, Leonardtown, MD

A local hot spot, this Mexican restaurant is great for lunch, dinner or catering your next party. They have lunch specials daily that are cheaper than eating a combo meal at a fast food chain. You… Read More

6 Best Speakeasies in Maryland!

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Social Coffeehouse and Speakeasy, Leonardtown, MD

While Social Coffeehouse might appear like a regular coffeehouse at first, it is actually home to one of the best speakeasies in Leonardtown, Maryland. The speakeasy is open with reservations only… Read More

6 Best Bookstores in Maryland!

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Fenwick Street Used Books and Music, Leonardtown, MD

This cute little book store off a lovely brick sidewalk is the type of bookstore you would imagine in a painting. You’ll fall in love before ever walking in the door. Once inside, the 23,000… Read More

10 Best Thai Restaurants in Maryland

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Sawatdee Solomons, Solomons, MD

This kid-friendly Thai restaurant has earned impressive online ratings from locals. Some of the chef specials include Pineapple Prawn Curry, Shrimp in Curry Powder, and Coconut Shrimp with Red… Read More

Best Pizza in Maryland: Our 9 Favorites!

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Nicoletti’s Pizza, California, MD

When in SoMo head to Nicoletti’s. They opened as a family-run restaurant in 1981 and have been serving classic recipes ever since. Being that the family is Italian, people come here for the… Read More

8 Best Lunch Spots in Maryland!

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The Reluctant Navigator Restaurant at Tall Timbers Marina, Tall Timbers, MD

This is classic Maryland at its best—on the water dining in a local establishment with fresh and tasty food. Driving to St. Mary’s County can take time so this is a good weekend lunch… Read More

8 Best Breakfast Spots in Maryland!

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The Frying Pan, Lusby, MD

You know how small communities always have a local joint they go to but no one else can find it? Yep, that’s the Frying Pan in Lusby. This southern part of Calvert County is gorgeous and… Read More

The 10 Best Museums in Maryland!

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Patuxent River Naval Air Museum, Lexington Park, MD

For a collection of aircrafts that include new F-35s head to Pa River Naval Air Museum. They have reserved a rich collection of naval aviation research and artifacts. You can climb inside of planes,… Read More

The 14 Best Picnic Spots in Maryland!

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Annmarie Sculpture Garden and Arts Center, Dowell, MD

Expose your family to innovative art by exploring the gallery and then picnic among the sculptures outside. This is an excellent place to visit if you are an art-lover or if you simply want to… Read More

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Holiday Light Festival

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Be Kind & Rewind: Ultimate 90s Tribute

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Shamrock Tenors

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Events Around Leonardtown

Home Grown Farm Market

Saturday, Nov 29, 2025 from 9:00am to 1:00pm

Lexington Park, MD

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Home Grown Farm Market

Saturday, Dec 6, 2025 from 9:00am to 1:00pm

Lexington Park, MD

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Home Grown Farm Market

Saturday, Dec 13, 2025 from 9:00am to 1:00pm

Lexington Park, MD

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Home Grown Farm Market

Saturday, Dec 20, 2025 from 9:00am to 1:00pm

Lexington Park, MD

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Home Grown Farm Market

Saturday, Dec 27, 2025 from 9:00am to 1:00pm

Lexington Park, MD

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Meals on Wheels America News - Easy Ways to Support

There are so many ways to give!... And they're all Tax-Deductible Your generosity helps Meals on...

Meals on Wheels America News - Are You Up for a World Food Day Challenge?

Every year, nearly 13 million older adults face food insecurity - unsure where their next meal wi...

American Red Cross News - It's the Season to Stay Safe

Stay Safe & Healthy Throughout the Holiday Season!James, the holiday season is meant for cele...

Meals on Wheels America Newsletter: Malnutrition Awareness, Senior Safety and More

Join us in fighting senior hunger September shines a light on the crisis of senior malnutrition ...

American Red Cross News - September is National Preparedness Month - Disasters Happen. Be Prepared When Emergencies Arise

Shop now and receive 10% off all Supplies and Products. SHOP NOW Dear James, With more frequen...

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Leonardtown Elementary School Fall Festival

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Christmas on the Square and Tree Lighting Ceremony

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Taste of St.Mary's

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Port of Leonardtown Winery

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Annual Somd Italian Heritage Festival

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Leonardtown Town Facts

Leonardtown, Maryland. Population for Leonardtown from the last gathering is 1896. You can view Leonardtown venues that host many Leonardtown MD events every year.

You can find a ton of properties for sale if you search the Leonardtown page on Zillow. Interest rates for Leonardtown are at historic lows as well.

Leonardtown Maryland has a latitude of 38.300300598145 and a longitude of -76.643096923828. View the full profile

In and Around Leonardtown, MD

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