Discovering Leonardtown Square

Discovering Leonardtown Square

Welcome to Leonardtown Square, the lively center of historic downtown Leonardtown! It's one of the few old town squares left from Maryland's past, and today it's bustling with activity. At the Upper Square, also called the War Memorials Garden, there's a special memorial for those who lost their lives in World War I. It honors 27 people from St. Mary's County.

Around the Upper Square, you'll find unique shops and nice places to eat. It's a great place to walk around. The Square is also where we have fun events like outdoor concerts, the Beach Party on the Square, and Christmas celebrations. These events bring lots of people to our town every year. Let's explore all the interesting things happening at Leonardtown Square!

Shopping in Leonardtown Square

Shopping in Leonardtown Square offers a diverse range of stores, including modern boutiques, artisan shops, and vintage stores, catering to various tastes. Each store has its unique character, ensuring there's something for everyone, from trendy clothing to handmade crafts.

Crazy for Ewe Yarns

At Crazy for Ewe Yarns, you'll see lots of colorful yarns and textures, making it a cozy place for knitters of all levels. They offer lessons for individuals and groups, perfect for beginners and pros alike. You can also find things like bags and scarves there. And don't forget to join their fun knitting events and classes to learn more and have a great time!

Shepherd's Old Field Market

Shepherd's Old Field Market is your destination for an abundance of treasures waiting to be discovered! With over 90 shops to explore, there's something for everyone. Check out some of the shops:

  • 10-4 Check Creation: Handcrafted beanies in various patterns, perfect for all ages! They even have styles for ponytail and "poof" lovers.
  • AddieJ Boutique: Sassy fashions and accessories for your little ones because they deserve to look stylish too!
  • Apple Mill: Add a special touch to your gatherings with etched glassware, serving boards, and other kitchen and decorative items.
  • Barclay Soap Company: Treat yourself to natural soaps, body butters, and other body care products with refreshing aromas, all expertly handcrafted right here in Southern Maryland!
  • Coastal Farms Boutique: Find the perfect gift or treat yourself with a variety of items like graphic mugs, jewelry, and fashion bags.
  • Colors of Quiche: Discover handcrafted bags and shoes from the Quiche region of Guatemala, supporting artisans and bringing wearable pieces of art to your wardrobe.

Come and explore Shepherd's Old Field Market for a day filled with shopping delights! For more shop options click here.

Fenwick Street Used Books

Fenwick Street Used Books provides a wide range of options for book enthusiasts and collectors. With offerings of both used and new books across various genres, customers can explore diverse literary interests. The store also features tarot cards, vintage vinyl records, and a selection of new and used puzzles and games for entertainment. Supporting local talent, Fenwick Street Used Books showcases works by artists and authors from the community. For those seeking the perfect gift, the store offers convenient gift certificates. Visitors to Fenwick Street Used Books are sure to find something captivating to enjoy.

Dine in Style

Eating in Leonardtown Square is more than just having a meal – it's a fun experience. The restaurants here offer food from different places and also support local farmers and fishermen. Whether you want fancy dining or a casual meal, there's something for everyone here. Come and enjoy the delicious food and great atmosphere at Leonardtown Square!

The Front Porch

At The Front Porch, you can enjoy tasty cocktails and craft beer in a cozy, old-fashioned house with seats on the porch. It's a small restaurant in historic downtown Leonardtown that serves creative Southern Coastal Cuisine. You'll dine in the Sterling House, which has a warm and comfortable atmosphere, and the staff is friendly and welcoming. We're a place where everyone in the community can come together to enjoy delicious food made with fresh, quality ingredients, all at a reasonable price.

Ye Olde Towne Cafe

Ye Olde Towne Cafe is a beloved family-friendly restaurant, known as a local favorite for breakfast and lunch. Offering American comfort food at affordable prices, it provides a cozy dining experience with options for seating at booths, tables, or the lunch counter. With a welcoming atmosphere, it's the perfect place to enjoy a meal with family and friends.

Sweetbay Restaurant & Bar

Sweetbay Restaurant & Bar is a sought-after spot for brunch, lunch, and dinner, featuring a diverse menu with coastal-inspired flavors. Guests can enjoy a range of delicious dishes from the brunch, lunch, and dinner menus, along with tempting desserts. The restaurant offers nightly specials to add variety to the dining experience. While dining, patrons can delight in live music and sample award-winning wine and slushies that perfectly complement the flavorful cuisine. Sweetbay Restaurant & Bar invites visitors to experience a culinary journey in a relaxed and inviting setting.

Antoinette's Garden

Antoinette's Garden, a charming café known for its gourmet coffee and wine offerings, provides a warm and inclusive environment for all visitors. The establishment boasts a diverse range of entertainment options, such as jazz bands, comedy shows, karaoke nights, trivia games, and board games, catering to guests of all interests. It prides itself on being a judgment-free space where negativity is left behind, encouraging patrons to come together for an enjoyable experience with family and friends. Step into Antoinette's Garden and embark on a journey of relaxation and fun.

Do Dah Deli 

Do Dah Deli is a cozy sandwich shop known for its custom creations and welcoming atmosphere. Offering a familial vibe, the deli serves up a variety of salads, soups, and sandwiches.

Exploring Activities in Leonardtown Square

Leonardtown Square isn't just about shopping and dining. It's a vibrant hub with plenty of things to do for everyone. From relaxing walks in the parks to exploring local history at museums, there's something for all ages. You can also enjoy cultural events like art festivals and live music performances. Plus, don't forget about the farmers' market and summer music series for even more fun. There's always something happening at Leonardtown Square to keep you entertained.

The Rex Theatre

The Rex Theatre is the perfect place to enjoy an evening out, whether with friends or on a date. This venue showcases spectacular award-winning national and regional acts from across the country, offering a diverse range of performances such as comedy shows and dueling pianos. Additionally, The Rex Theatre provides space for rentals for weddings and private events. Seating options cater to everyone, from full-service VIP tables to balcony seating and standing room. Before or after the show, be sure to indulge in the restaurant's local fare and craft beverages.

The Old Jail Museum

Explore the Old Jail Museum, a historic gem built in 1876 and the oldest sheriff's office in the nation. Discover original cells, jail keeper's quarters, and a fascinating collection of artifacts. Also, find visitor information, a museum store, and connections to local history like Civil War Trails and the Underground Railroad Network to Freedom.

Breton Bay Golf & Country Club

Breton Bay Golf & Country Club is a delightful destination for leisure and relaxation, offering a variety of amenities in a picturesque environment. Visitors can enjoy a beautiful golf course, spacious swimming pools, and lighted tennis courts for evening play. The Club House, open to the public, features the inviting Ironwood Grill, serving delicious breakfast, lunch, and early evening meals. Additionally, guests can unwind at the full-service bar offering beer, wine, and mixed drinks. Whether they're members or guests, visitors to Breton Bay Golf & Country Club are sure to have an enjoyable experience filled with fun and relaxation.

Sunset Cruise

Step aboard a Sunset Cruise with Captain Phil and Fish the Bay Charters for an unforgettable evening on the water. Departing from either Leonardtown Wharf or Point Lookout Marina, guests can choose their preferred route for a scenic adventure. Sail along Breton Bay, the Potomac River, and St. Clement's Island from Leonardtown Wharf, or opt to explore the tranquil waters of the St. Mary's River from Point Lookout Marina. Whichever route you select, you'll be treated to breathtaking views and the soothing ambiance of the setting sun. As you cruise, Captain Phil will share fascinating insights about the area's history and natural beauty, making your journey both relaxing and educational. So sit back, unwind, and let the gentle waves and golden hues of the sunset provide the perfect backdrop for an evening of tranquility and connection with the water.

Services Available at Leonardtown Square

Leonardtown Square is home to numerous neighborhood businesses and essential services in addition to stores and eateries. It offers a lot, from community facilities to auto repair. Everything you require, including bakers, florists, and hardware stores, may be found here. By patronizing these companies, you can foster neighborhood growth. One famous location is the Leonardtown Collision Center, which has a stellar reputation for auto repair. For your needs, there are also banks, medical facilities, and other things. Everybody can enjoy the events and activities offered by local establishments like the Leonardtown Library - St. Mary's County Library and the Leonard Hall Recreation Center. The main goal is to improve and ease everyone's lives in Leonardtown Square. Check here for more Local and Community Businesses

Events and Festivities at Leonardtown Square

In Leonardtown Square, there are many fun events and parties all year round that bring everyone together. From special celebrations to cultural festivals, there's always something exciting happening. People can join in and have a great time being part of the community. The events make Leonardtown Square even livelier and happier. Check this Leonardtown Events Calendar for more updates.

Leonardtown Summer Music Festival

The Leonardtown Summer Music Festival is a fantastic event held in Historic Leonardtown, Maryland. It features free concerts, where people can enjoy live music and dance the night away. There's also delicious food to indulge in, along with raffles, prizes, and other fun activities for everyone to enjoy. It's a wonderful way to spend a summer evening with family and friends, creating lasting memories in the heart of Leonardtown.

Christmas on the Square & the Annual Tree Lighting Ceremony

Christmas on the Square in the Town of Leonardtown is a magical event that marks the start of the holiday season. It kicks off with the annual Christmas Tree Lighting ceremony, where Santa makes a special appearance. The Town Square comes alive with holiday music, entertainment, and a variety of festive activities for everyone to enjoy. From horse and carriage rides to sleigh rides, train rides, and hayrides, there's something for everyone. Visitors can also experience a live nativity scene, petting zoo, face painting, and children's crafts. And don't forget to indulge in hot drinks and fresh kettle corn while strolling around the beautifully decorated downtown area, where many restaurants and shops will be open for holiday shopping and dining. It's a joyous celebration that brings the community together in the spirit of the season.

At the heart of Southern Maryland, Leonardtown is known for its cozy charm and strong sense of community. Whether you're enjoying a peaceful sunset cruise, joining in on the excitement of summer festivals, or embracing the joy of holiday traditions, Leonardtown Square is where it all happens. The Southside Group is here to help you make the most of life in this vibrant area. From helping you find your dream home to connecting you with local culture, our team is dedicated to ensuring you have the best experience in Southern Maryland.

Connect with us today and start your journey toward making lifelong memories in Leonardtown. Let us guide you home to the charm, the festivities, and the vibrant community that is waiting to welcome you.

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