News Release, Leonardtown Business Association

Leonardtown, MD- Are you looking for 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 variety of exciting activities and events taking place throughout Town all weekend. How about wining and dining and doing a little Salsa dancing with that special someone, gathering a group of friends for a creative evening at a group art workshop, or taking a trishaw ride around Town.

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 Fun Things to Do in Leonardtown this Valentine’s Day Weekend – Friday, February 14th – Sunday, February 16th.  

Free Romantic Trishaw Rides Through Historic Leonardtown
Cycling Without Age, St. Mary’s County is offering free, 30-minute romantic rides for two passengers at a time through Historic Downtown Leonardtown.Stops around Town include treats, wine and many Valentine’s Day surprises courtesy of participating businesses – David’s Flowers, North End Gallery, Arts Council, Crazy for Ewe, The Good Earth Natural Foods Company and Fenwick Street Used Books! Registration required. To reserve your spot, email Christina Allen at:

Wine & Design Couples Date Night & Mommy and Me Owls Workshop
Sip a little wine and create a little art with that special someone on Valentine’s Day, Friday, February 14th from 6:30 p.m. – 8:30 p.m. and/or bring the little ones in your life for a Mommy and Me Owls afternoon workshop on Sunday, February 16th from 2:00 p.m. – 4:00 p.m. Artists guide guests step-by-step in creating their own masterpieces to take home. One ticket secures both seats. For more information or to make a reservation, visit:

Vivian VanDam Book Signing at Fenwick Street Used Books
The lovely Vivian VanDam is a local author and will be signing her books at the shop on Valentine’s Day, February 14th, from 4:00 p.m. – 7:00 p.m. Books will be available for purchase or you may bring your own. Come chat it up with this up and coming author and see what she has in store for new books this year! Follow her adventures on her Facebook page 

10% off Valentine’s Day Smoothies at the Good Earth
The Good Earth Natural Foods Company will offer a special Valentine’s Day Smoothie at 10% off. They will also be giving away a box of “Divine White Chocolate with Strawberry Hearts” to each couple that stops by via Christina Allen’s Cycling Without Age Trishaw Ride up to 10 (one per arrival, couples and single riders are both welcome)

Free Gift with Purchase at the St. Mary’s Arts Council
The St. Mary’s Arts Council will be offering a free gift with any purchase from their Gallery & Gift Shop on Valentine’s Day, 11:00 a.m. – 4:00 p.m. Stop by and find that perfect gift for that special someone.

Special on Drinks and Cigars at Leonardtown Cigars
Leonardtown Cigars is offering a Valentine’s Day special of two drinks and a cigar for $20. Or two drinks and two cigars for $25 on Friday, February 14th from 4:00 pm to close.

Four-Course Valentine’s Day Dinner at the Front Porch
Enjoy a four-course Valentine’s Day Dinner at the Front Porch (Appetizers, Soup & Salad, Main Course and Dessert). This is the perfect recipe for a romantic evening for two or a celebration with family and friends.

Open Hearts: Couples Yoga at root, SUP & Fitness
Continue your weekend celebration with Valentine’s Day Yoga for Couples with your loved one on Saturday, February 15th at 5:30 pm. $25 per couple.

Sip & Salsa at Port of Leonardtown Winery
Dance the night away at Port of Leonardtown Winery on Saturday, February 15th from 6:30 p.m. – 10:30 p.m. Your ticket includes a dance lesson in the tank room, live salsa DJ, a glass of sangria or wine, and 3 hours of open dancing on our heated patio. Couples and singles are welcome (no partners are needed). This would make a fun romantic outing for two or a great evening with friends.

Bottomless Mimosas at Social Coffeehouse
For a delicious ending to your Valentine’s Day Weekend, visit Social Coffeehouse for Bagel Sammies from Brooklyn Bagel Company and Bottomless Mimosas on Sunday, February 16th from 11:00 a.m. – 4:00 p.m.  Website:

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 Leonardtown Square this Valentine’s Day Weekend! For more information on what to See & Do in Leonardtown, Maryland, visit

David M. Higgins II is an award-winning journalist passionate about uncovering the truth and telling compelling stories. Born in Baltimore and raised in Southern Maryland, he has lived in several East...