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One of my favorite places to go for delicious food and drinks is Leonardtown. In the historic Leonardtown Square, there are several great restaurants/food establishments. There are also some fabulous places just off the Square.

These businesses are following guidelines to ensure the safety of their patrons during the Coronavirus. They are finding ways to make it work! Please give them your business, this will keep them open during these difficult times.

On the Leonardtown Square are:

Sweetbay

  • 22680 Washington Street
  • Leonardtown, MD
  • 240-309-4148

The newest restaurant on the Square is Sweetbay, and it is a welcome addition. This new restaurant (open since January) serves elevated and eclectic cuisine. The interesting menu along with the flavors of the food bring fine dining to Southern Maryland. I wrote about this restaurant on August 11, 2020 (see link below).

Sweetbay hours:

  • Monday – 4:00pm to 9:00pm
  • Tuesday-Wednesday – 11:30 am to 9:00 pm
  • Thursday-Saturday – 11:30 am to 9:30 pm
  • Sunday – Closed

The lunch menu is served from 11:30am to 3:30pm.

Facebook page – https://www.facebook.com/SweetbayMD

Website – http://sweetbayrestaurant.com/

Link to article- SweetBay

The Rex

  • 22695 Washington Street
  • Leonardtown, MD
  • 301-475-1512

Located in a former movie theater, The Rex, offers appetizers, soups & salads, burgers, sandwiches, and pizzas, using fresh ingredients. According to their website, “Their goal is to provide patrons with an excellent dining experience.” They have daily specials, Sunday brunch, weekly events, and live music. Some of the weekly specials include, ½ price appetizers and Pint Night on Mondays, Trivia and Taco Tuesday, and Wingin It Wednesday. They also have bottomless Mimosas at Sunday Brunch.

The have inside dining, outside dining (depending on the weather), and carryout.

I have not dined at The Rex yet, but plan to go in the future.

The Rex hours:

  • Monday-Friday – 4:00pm to 8:00pm
  • Saturday – 11:00am to 1:00am
  • Sunday – 11:00am to 3:00pm

Facebook page – https://www.facebook.com/therexleonardtown

Website – https://therexmd.net/

Ye Old Towne Café

Classic diner-style food, serving breakfast all day. Another restaurant on my list to visit because I love breakfast.

Ye Olde Towne Café hours:

  • Monday-Friday – 7:00am to 2:00pm
  • Saturday and Sunday – 8:00am to 2:00pm

Ye Old Towne Café Facebook page – https://www.facebook.com/YeOldeTowneCafe/

Heritage Chocolates

  • 22699 Washington Street
  • Leonardtown, MD
  • 240-587-3123

What is behind the nondescript brick building on the Square in Downtown Leonardtown? Only the sweetest place around! Heritage Chocolates is a shop full of goodness. Open since September 2016, owners Terra and Chris serve up delicious homemade chocolates, candies, and Gelato. I was told their most popular chocolate is the Sea Salt Caramel. Yep, I agree! I get a box every time I go…so good! I also love the Peanut Butter Meltaways, the Caramel Applies, and (seasonally) Chocolate Covered Strawberries. They also have an enrober. This is a machine that coats the fillings with chocolate. It is the machine made famous by Lucille Ball and the candy shop episode on I Love Lucy. It is fascinating to watch! The homemade Gelato is delicious too! I love the pistachio flavor; it is my favorite.

Heritage Chocolates hours:

  • Monday-Thursday – 10:00am to 7:00pm
  • Friday and Saturday – 10:00am to 8:00pm
  • Sunday – 12:00pm to 5:00pm

Facebook page – https://www.facebook.com/HeritageChocolates/

Website – https://www.heritagechocolateshop.com/

Some great restaurants are located just off the Leonardtown Square. They include the following:

Jessie’s Kitchen

  • 22845 Washington Street, Unit C
  • Leonardtown, MD
  • 301-997-0888

One of my favorite Leonardtown eateries is Jessie’s Kitchen. Located just down the street from the Square, Jessie’s Kitchen is Asian Fusion and so much more. Jessie has everything from small plates (designed to be shared) to noodle soups, burgers, and amazing entrees. Last time I went, we shared several small plates, and they were delightful. The bulgogi is delicious too!

Jessie’s Kitchen hours:

  • Monday-Thursday – 12:00pm to 8:00pm
  • Friday and Saturday – 12:00pm to 8:30pm
  • Sunday – Closed

Facebook page – https://www.facebook.com/Jessieskitchen.LT

Link to article – https://southernmarylandchronicle.com/2019/09/09/sip-and-bite-encounters-with-lynne-omeara-jessies-kitchen/

Link to article – https://southernmarylandchronicle.com/2020/05/12/sip-and-bite-encounters-with-lynne-omeara-restaurant-revisits-dat-jerk-and-jessies-kitchen/

The Slice House

  • 41565 Park Avenue
  • Leonardtown, MD
  • 301-997-6577

Owners Ken and Maegyne Held (with help from their son, John) have found the secret to making great pizza!

The pizza is sold only by the slice. Their dough is made fresh, in-house, every day. They make their own sauce too, using the best ingredients. The cheese is from Wisconsin and has no additives or caking agents. They hand-toss the pizza and it goes on 18-inch pans. The crust is perfectly thin, which is the way I prefer it. The balance of crust and toppings is perfect! It is the perfect place for lunch…pizza and a beer from the bar!

They only sell pizza by the slice and they have all their offerings on display for you to choose from. The pizzas are cooked in the brick oven partially, then finished off in the oven after you order. Every day they have the standards…cheese, pepperoni, sausage/pepperoni, veggie, supreme, and chicken cilantro. They rotate specialty flavors. For whole pizza pies, go around the corner to The Slice House II Go.

The Slice House hours:

  • Tuesday-Saturday – 11:00 to 2:00pm
  • Sunday and Monday – Closed

Facebook page – https://www.facebook.com/TheSliceHouseLeonardtown

Website – https://www.theslicehouse.com/

Link to article: https://southernmarylandchronicle.com/2019/06/10/somd-taste-and-sip-encounters-with-lynne-omeara-slice-house/

Link to article – https://southernmarylandchronicle.com/2020/01/14/somd-taste-and-sip-encounters-with-lynne-omeara-slice-house-part-2/

Link to article – https://southernmarylandchronicle.com/2020/04/21/sip-and-bite-encounters-with-lynne-omeara-restaurant-revisit-ruccis-and-the-slice-house/

The Slice House II Go

  • 22745 Washington Street
  • Leonardtown, MD
  • 301-997-6577

Because their pizza and bagels sell out almost every day, owners Ken and Maegyne Held decided to add a second location, where they now have the capability to bake twice as much deliciousness. The Slice House II Go is in the former Big Larry’s Eatery space on Washington Street in Leonardtown.

The Slice House II Go offers amazing fresh-made whole pizzas and NY-style bagels. All the ingredients are the best quality, and the pizza dough and sauce are made inhouse.

Not only do they often sell out of pizza, but they also sell out of bagels! Most bagel mornings, they sell out of bagels by 9:00am. The bagels are started the night before, then boiled and baked (in the brick oven) in the wee hours of the morning. Every week they have typical bagel flavors (such as plain, poppy seed, sesame seed, salt, everything, garlic) plus a special one.

The Slice House II Go hours:

  • Tuesday and Wednesday – 3:00pm to 7:00pm
  • Thursday-Saturday – 11:00am to 8:00pm
  • Sunday and Monday – Closed

Bagel hours:

Thursday-Sunday – 6:30am to 10:00am (or sold out)

Facebook page – https://www.facebook.com/TheSliceHouseLeonardtown

Website – https://www.theslicehouse.com/

Link to article: https://southernmarylandchronicle.com/2020/07/28/sip-and-bite-encounters-with-lynne-omeara-the-slice-house-ii-go/

The Front Porch

  • 22770 Washington Street
  • Leonardtown, MD
  • 301-997-1009

The Front Porch is a cozy restaurant featuring creative Southern fare, interesting cocktails, and craft beer.  Set within the historic Sterling House, they offer casual dining and serve as a place to enjoy fresh, quality ingredients at an affordable price.

The menu includes a broad selection of starters, soups, sandwiches, salads, and entrées. They have daily specials, feature seasonal ingredients, local produce, and a great dessert menu.

The food is fabulous! I have been several times but have not written an article yet. Be on the lookout for a review soon.

The Front Porch hours:

  • Monday-Thursday – 11:00am to 9:00pm
  • Friday and Saturday – 11:00am to 10:00pm
  • Sunday – 10:00am to 3:00pm

Facebook page – https://www.facebook.com/The-Front-Porch-in-Leonardtown-135774109816109/

Social Coffeehouse and Cocktail Bar

  • 41658 Fenwick Street
  • Leonardtown, MD
  • 301-475-2400

On Fenwick Street, one block from the Leonardtown Square is a neighborhood coffeehouse and cocktail bar. According to their website, “Social is built on the Buy Local philosophy, and artfully combines local ingredients into mouth-watering espresso, cocktails, light fare, and gourmet tapas. The coffeehouse serves organic, fair trade, and environmentally responsibly sourced coffee, espresso, and teas from the Chesapeake Bay Roasting Company (CBRC). The coffee and espresso are imported green and fully roasted at CBRC’s roasting facility in Crofton, Maryland. The cocktail bar offers gourmet light fare and premium artisan cocktails, embracing current trends in cocktail crafting and presentation.”

Social Coffeehouse and Cocktail Bar hours:

  • Monday and Tuesday – Closed
  • Wednesday – 6:30am to 4:00pm
  • Thursday – 6:30am to 6:00pm
  • Friday – 6:30am to 11:45pm
  • Saturday – 7:00am to 11:45pm
  • Sunday – 7:00am to 4:00pm

Facebook page – https://www.facebook.com/socialonfenwick/

Website – https://socialonfenwick.com/

Old Town Pub

  • 22785 Washington Street
  • Leonardtown, MD
  • 301-475-8184

Just down the street from Leonardtown Square is the Olde Town Pub. They offer a fun, casual dining and drinking experience in. They have 14 beers on tap, as well as award winning chicken wings. They serve daily specials, including Wing Night Mondays, Pizza and Pitcher Tuesdays, Wine Down Wednesdays, Pint Night Thursdays, and $5.00 off buckets of beer on Sundays. I have been several times; the food was great, and the atmosphere comfortable.

Old Town Pub hours:

  • Monday-Wednesday – 3:00pm to 1:00am
  • Thursday – 3:00pm to 2:00am
  • Friday – 2:00pm to 2:00am
  • Saturday – 12:00pm to 2:00am
  • Sunday – 12:00pm to 12:00am

Facebook page – https://www.facebook.com/Oldetownpubmd/

Website – https://oldetownpub.com/

Do Dah Deli

  • 22845 Washington Street, Unit D
  • Leonardtown, MD
  • 240-309-4134

One of the newest food establishments on Washington Street is Do Dah Deli. They offer sandwiches, salads, subs, soups, desserts, and a kid menu. They serve house made items using fresh ingredients. I plan to visit Do Dah Deli soon.

Do Dah Deli hours:

  • Tuesday-Friday – 9:00am to 2:00pm
  • Saturday-Monday – Closed

Facebook page: https://www.facebook.com/DoYouDoDah/

Website: https://www.dodahdeli.com/

Oga’s Asian Cuisine

  • 22745 Washington Street
  • Leonardtown, MD
  • 201-475-0188

Oga’s Asian Cuisine, on Washington Street, serves Chinese and Japanese cuisine. The sushi is very popular. Oga’s has dining in, or carryout. This is another restaurant I want to check out.

Olga’s Asian hours:

  • Tuesday-Thursday – 11:00am to 8:30pm
  • Friday and Saturday – 11:00am to 9:30pm
  • Sunday – 11:00am to 8:30pm
  • Monday – Closed

Facebook page – https://www.facebook.com/pages/Oga’s/163625360315514/

Website: https://www.orderogasasiancuisine.com

Brudergarten Beer Garden and Botanics Deli-Cafe at Shepherd’s Old Field Market

  • 22725 Duke Street
  • Leonardtown, MD

Shepherd’s Old Field Market – This is a great, fun place to spend an afternoon. According to the market website, “Whether you are looking for that unique home décor item or special gift, or just feel like spending an afternoon browsing through nearly 60 shops and services in our mini-mall, Shepherd’s Old Field Market has something for everyone and there’s always something new! Stop in and enjoy a cold, frosty beverage at our Brudergarten Beer Garden, or a cup of coffee and breakfast or lunch at Botanic Coffee Shop & Deli! And when you’re ready to work it off, check out the classes at root SUP & Fitness!

Shepherd’s Old Field Market hours:

  • Wednesday-Friday – 10:00am to 7:00pm
  • Saturday – 9:00am to 7:00pm
  • Sunday – 9:00am to 5:00pm
  • Monday and Tuesday – Closed

Facebook – https://www.facebook.com/Shepherdsoldfield

Website – https://shepherdsoldfield.com/

Phone – 240-309-4067

Link to article – https://southernmarylandchronicle.com/2019/09/30/sip-and-bite-encounters-with-lynne-omeara-shepards-old-field-market/

Brudergarten Beer Garden – Offers locally-produced craft beers, popular bottled labels, spirits, wines, and specialty cocktails! They have 16 beers on tap and have flights available. On Sundays, they have bottomless Mimosas between 11:00am and 3:00pm. They have a bar menu available. I have been here many times and it is a lot of fun. They have games and it is family-friendly.

Brudergarten Beer Garden hours:

  • Monday – 8:00pm to 12:00am
  • Tuesday – Closed
  • Wednesday and Thursday – 4:00pm to 10:00pm
  • Friday – 4:00pm to 12:00am
  • Saturday – 11:00am to 12:00am
  • Sunday – 11:00am to 7:00pm

Facebook page – https://www.facebook.com/brudergarten

Website – https://www.brudergarten.com/

Phone – 240-753-3332

Botanic Deli-Café – Enjoy a selection of menu items including salads, sandwiches, beverages, soups, and desserts, including vegetarian and vegan options! I have been here many times, and the food is fantastic!

Botanic Deli-Café hours:

  • Wednesday-Friday – 10:00am to 4:00pm
  • Saturday and Sunday – 9:00am to 4:00pm
  • Monday and Tuesday – Closed

Facebook page – https://www.facebook.com/botanicdelicafe

Website – https://www.botanic.cafe/

Phone – 240-307-0855


Lynne O'Meara

Lynne recently retired after 30 years of federal service with the Office of Naval Intelligence. She is now a full-time Commercial Real Estate Agent with Shasho Consulting, Commercial Real Estate. She...

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