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Discover All There is to Love About Leonardtown Valentine's Day Features:

10 things

10 Things We Just Love in Leonardtown This Valentine's Day Weekend 

Friday, February 12th - Sunday, February 14th


Whether you’re looking for that perfect gift for that someone special or trying to find something romantic, family-friendly or a little out of the ordinary to do this Valentine's Day Weekend, Leonardtown, Maryland has everything you need to celebrate those special people in your lives with a delicious array of specialty gifts and treats to choose from and an exciting variety of activities and events taking place both virtually or throughout Town all weekend. How about wining and dining and creating a little art with that special someone, gathering a group of friends for a creative evening at a group workshop, or taking in a virtual concert in the comfort of your own home. No matter how you want to celebrate this special holiday weekend, you're sure to find the perfect way here in Leonardtown. Here is a look at 10 Things We Just Love in Leonardtown this Valentine’s Day Weekend (Friday, February 12th - Sunday, February 14th).  


  1. Port of Leonardtown Winery & Noli’s Ultimate
    Valentine’s Day Package

    The Port of Leonardtown Winery is teaming up with Noli’s Sweet Tooth to help you pamper your significant other with the ultimate Valentine’s Day package – a romantic gift that includes two pastries of your choice and a delicious bottle of wine presented in an elegant gift box. Choose from Noli’s limited-edition éclair filled with velvety pastry cream adorned with a rich chocolate glaze and Valentine’s Day garnish or the limited-edition chocolate covered strawberry-themed cannoli filled with fresh strawberry cream topped with freeze dried strawberries. For the finishing touch, Nolis’ dips the end of the shell in chocolate and tops the creation with powdered sugar. AVAILABLE THROUGH PRE-ORDER ONLY! – (click on Pre-Orders).

  2. Enjoy a Virtual Valentine’s Day Celebration 
    Join us on Saturday, February 13th (Valentine’s Day Weekend!) for the premiere of Leonardtown Arts & Entertainment, a new online show that features exciting performances and spotlights on local artists and performers. The show kicks off with a Virtual Pre-Valentine’s Day Concert with Southern Maryland Recording Artist, Phillip Michael Parsons! The concert, filmed at the Olde Town Pub in Leonardtown, features Phillip performing popular Country and Rock favorites along with some of his original hit songs. Order a special Valentine’s Day Dinner from Olde Town Pub or Quality Street Kitchen & Catering and make it a date night at home or a fun evening with friends (Galentine Celebration anyone!?!)! Tune in at or the Town of Leonardtown Facebook page at 8 PM for a Valentine’s Day Celebration you’re sure to love.

  3. Social Coffeehouse Helps You Sip and Savor
    with the Ones You Love 

    Social Coffeehouse invites you to Celebrate being single, taken, or happily committed to your daily cup of caffeine with a delectable choice of three sweet treats that they’ve whipped up for you. Choose from their Iced Chai with Raspberry Cold Foam, Raspberry Truffle Latte (raspberry + dark chocolate), or Strawberries and Cream Smoothie with White Chocolate. Treat yourself and someone you love to one of these tasty treats. Make it a special outing by cozying around one of their outdoor fire pits.

  4. Wine & Design Couples Date Night, Galentine & Mommy and Me Workshops 
    Live & Virtual Celebrations:
    Sip a little wine and create a little art with that special someone or just the gals on Valentine's Day Weekend and/or bring the little ones in your life for a Mommy & Me (or Daddy & Me) outing. Choose from a variety of lovely works of art from the adorably sweet to the touchingly romantic – there’s something for everyone. Pick up dinner from a local restaurant to enjoy while you sip & paint to your hearts content. Kits are also available to create your works of art from the comfort of your home. For more information or to make a reservation, visit:

  5. Botanic Deli & Café Breakfast Boxes for Two 
    Botanic Deli & Café has the perfect way to treat the one you love to breakfast in bed. The special someone in your life is sure to enjoy waking up to a delicious breakfast box from the café. Each box contains a Large coffee or Tea, 2 Turkey & Cheese Croissants, 2 chocolate chip muffins, 2, 12 oz Organic Orange Juice., and Strawberries (garnish). There are gluten free and vegetarian Boxes available as well. Order by February 11th and pick up February 14th -

  6. Free Gift Wrapping at the St. Mary's County
    Arts Council

    The St. Mary's Arts Council will be offers free gift wrapping with any purchase that fits into their totes! Come shop from the work of over 40 local artists including pottery, jewelry, paintings, prints, and much more. Stop by and find that perfect gift for that special someone.

  7. Chocolate Covered Strawberries from Heritage Chocolates are Back! 
    Heritage Chocolates famous, decadent chocolate covered strawberries are back and are now available for pre-order online and in the shop! Choose from milk, dark and white chocolate options - pre-order now for pick-up dates of February 13th and 14th! There is also a variety of tempting, hand made treats available from a wide assortment of custom confections. Choose from one of their elegant pre-packaged gifts or select your favorites from their amazing Chocolate Bar! Of course, you can’t go wrong with their Chocolate Covered Strawberries – their most popular item this time of year. To order, visit:

  8. Dine in Elegance at the Front Porch
    Celebrate Valentine’s Day Early with an elegant, four-course dinner at The Front Porch on Saturday February 13th from 5-10pm. Enjoy a Prix fixe 4 course Porch Experience with that special someone! In-person dining only. Reservations are available through their Website or by Phone or (301) 997-1009. 

  9. Taste the Sweet Life at Sweetbay!
    Sweetbay Restaurant & Bar will celebrate Valentine’s Day all weekend long. Specials will include the spiced and seared jumbo butterflied shrimp, guacamole, and cucumber. They will also be running Surf and Turf, seabass specials as well and offering a special dessert from Morgan Salee’s Cheese-Cakery and more all weekend long! Make your reservations early! –

  10. Home Baked Goodness from Cakes by Amanda, LLC
    For locally, home baked goodness, visit Cakes by Amanda, LLC at Shepherd’s Old Field Market. Choose from a variety of delicious treats from delicious single and mini-cookie sets and fabulous cocoa bombs, to a selection of Candy Club candies, and other goodies! Cakes by Amanda is located down the center of the main floor of the Market! You’re sure to find the perfect sweet treat for your loved ones or yourself!


1. Ultimate Valentine's Day Package

2. Valentine's Day Virtual Concert Featuring
    Phillip Michael Parsons

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Social Latte.jpg

3. Social Coffeehouse VD Specials

4. Wine & Design Mommy & Me Classes

5. Botanic Deli & Cafe Breakfast Boxes
For Two

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6. Free Gift Wrap at St. Mary's County Arts Council

7. Chocolate Covered  Strawberries from Heritage Chocolates

8. Dine in Elegance at the Front Porch

9. Taste the Sweet Life at Sweetbay

This is just a small portion of the exciting things there are to do here in Leonardtown. There are countless options for fine dining and entertainment. No matter your interest, there’s an option for you. We hope to see you and your loved ones around the Leonardtown this Valentine’s Day Weekend! (Individual specials are subject to change, please contact businesses directly for updated info)


10. Home Baked Goodness from 
Cakes by Amanda, LLC


Sample Valentine's Day Itineraries

Grey Paint

Jess & Andrew

Discovering Leonardtown Host, Andrew Ponti, and his lovely wife, Jess chose Date Option No. 1: A Couple's Sip & Paint Night at Wine & Design followed by  enjoying a Raspberry Truffle Latte by the fire pit at
Social Coffeehouse.

Discovering Leonardtown_VD_Andrew and Je

"We really liked being able to do something different and creative..."



Phillip & Stephanie

Our First Couple, Phillip & Stephanie chose Date Option
No. 2
: Dinner at
Salsa's Mexican Cafe followed by a game of pool at Action Lounge & Billiards

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"We love any opportunity we get to try something new."



Derek & Destiny

Our Third Couple, Derek & Destiny chose Date Option
No. 3: A Wine Tasting and enjoying Live Music at the
ort of Leonardtown Winery

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"The staff was extremely welcoming and knowledgeableThis was a great 
afternoon out.




Emily & Nick

Our Fourth Couple, Emily & Nick chose Date Option No. 4: Dinner at The Front Porch a Challenge at the Escape Rooms Southern Maryland

Emily & Nick.png

"We really enjoyed our date in Leonardtown. - from the fantastic meal to reinforcing our bond by working together as a team. We had a great time!

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