The Best Wedding Venues in Leonardtown, MD

Located in the rolling hills of Maryland between Frederick, MD and Washington, D.C., Milton Ridge boasts exquisite setting and exceptional services. The beautifully restored Milton Ridge Historic Chapel and Reception Hall have been created exclusively for beautiful weddings and occasions with special attention given to every detail. Having your wedding ceremony and reception all in one location will make your wedding planning much easier. It gives you more control over timing and flow, as well as make things easier for your guests. At Milton Ridge, our event coordinator will assist in the planning of every detail of your wedding or special event. We have the ability to customize every detail to meet the specific needs for your special event. With our unique all-inclusive pricing, there are no surprises. You know the true costs up-front, which makes budgeting easier. It also allows us to offer beautifully personalized events at a tremendous value.

Flora Corner Farm, a working farm in southern Maryland, offers a tranquil setting for weddings and parties. Just 1.5 hours from Washington D.C., Annapolis, and Virginia, the farm features fields of soybeans, corn, and sunflowers, providing a beautiful backdrop for both barn weddings and intimate garden ceremonies. Perfect for smaller events, FCF can also accommodate up to 130 guests on its lawn. Recent bride Jessi K raves about the farm and its owners, praising their dedication and attention to detail in creating a perfect wedding experience.

Welcome to Swan Point Yacht & Country Club, the ideal venue for your dream wedding. Nestled on the serene shores of the Potomac River, our charming venue provides a stunning backdrop for your special day. Our experienced team is dedicated to bringing your unique vision to life. Exchange vows in our picturesque outdoor ceremony site, with panoramic views of the Potomac River and lush green surroundings. Transition to our elegant reception venue for a stylish celebration with your guests. At Swan Point Yacht & Country Club, we ensure a stress-free and memorable wedding day. Our attentive staff will guide you through every detail, allowing you to relax and cherish the moment. Whether it’s a grand celebration or an intimate gathering, we offer the perfect setting for your dream wedding. Contact us today to explore customizable wedding packages and start planning your perfect day.

Serenity Farm is a place where history, nature, and celebration come together in a way that feels both timeless and deeply personal. Set along the quiet, scenic shores of the Patuxent River, the farm offers couples a wedding experience rooted in authenticity—rustic charm, historic character, and sweeping waterfront views that make every moment feel unforgettable. For couples seeking a venue that is beautiful without being pretentious, elegant without being artificial, and naturally romantic without needing heavy décor, Serenity Farm stands out as one of Southern Maryland’s most captivating wedding locations.

Originally named St.Mary's Rectory this property was inducted into the National Register of Historic Places in 1987 and remains true to it's original mid-19th-Century appearance.Nestled in the quiet corners of Aquasco,MD. Roselynn Manor is the perfect destination for your dream event. Boasting 5 acres the property is rich in legacy dating back to 1849 making it a cherished landmark into ur community.

Host your next unforgettable event at Marcellus Farms™, where elegance meets nature. Whether you envision a grand gathering in Manor En Noire, a rustic yet refined celebration in our Luxe Barns, or an open-air experience with our Outdoor Rentals, we offer versatile spaces tailored to your needs. From intimate gatherings to large-scale events, our estate provides the perfect setting for weddings, corporate retreats, and special occasions. Book your venue today and bring your vision to life!

For over 30 years, Herrington on the Bay has transformed waterfront dreams into unforgettable wedding realities. We know you'll be captivated by our panoramic Chesapeake Bay views and our delectable, locally-sourced menus. But what truly sets us apart is the unparalleled service we deliver. When you choose Herrington's full-service wedding package, we take care of everything: the venue, planning and coordination, exquisite food and beverage service, attentive staff, and stunning on-site amenities. We'll also collaborate with you to craft a customized menu featuring sustainable ingredients from our trusted partner farms. Let Herrington on the Bay orchestrate your luxurious waterfront wedding, a celebration as exquisite and unforgettable as your love story.

Farm 1750 has reimagined our historic farmhouse into the perfect Virginia Countryside Wedding Venue. Established in 1750 this working farm has endured through generations and awaits you and yours. Start your legacy today at Farm 1750 Novacelli means New Barn in Porteguese - our amazing barn has retractable walls and ceiling so you can create the perfect venue location for your special day. Historic Farmhouse Charm Prepare for your wedding day in an authentic farmhouse built in 1750. All the character retained, but no modern comfort spared.

We are a place where you can express your unique vision and bring your wedding dreams to life. There are a few different ways to celebrate your wedding weekend here at Wylder. Depending on headcount and date availability. From intimate waterfront escapes to extravagant weekend-long festivities, we have the perfect package for you! We have over 9 acres of lush grounds, 50 hotel rooms, 1100 feet of private waterfront & over 4,000 sq. feet of indoor & outdoor waterfront flexible event space for you to plan the custom wedding of your dreams! * Hotel rooms are booked by your guests *

Family-owned, boutique, Virginia farm winery, serving delicious, award-winning Virginia wines. Both our Stables and Dairy Barn tasting rooms are fully handicap accessible. No reservations are needed or required for our tastings. We have ample seating provided! We are a family & pet-friendly winery! Yes! Your fur baby is welcome inside our tasting rooms, as long as they are well-behaved and on a leash. Look for fun food trucks, pop-up sips and shops, amazing bands, and some of the most fantastic, authentic Spanish Sangria you have ever tasted in your life. Plus, delicious wine slushies too!

The Anchorage, with origins back to 1800, is a venue set on 12 private acres with waterfront views situated on the beautiful Choptank River. We offer a relaxed, peaceful and romantic experience on the shores of the river, which is part of the Chesapeake Bay waterway. The venue includes an open air, covered pavilion with spectacular waterfront views for up to 100 people.

The Osprey's at Belmont Bay is a charming waterfront venue filled with natural beauty and a laid back luxury. With the picturesque Occoquan River providing a naturally breathtaking backdrop, the venue features a beautifully adorned ballroom and spacious accommodations for up to 146 guests. Our outdoor ceremonies are truly enchanting with a flagstone aisle leading to a pergola framed by a beautiful waterfront view.

Welcome to Harbour View — where we make your dreams a reality. Every year we host hundreds of weddings and special events located right on the Occoquan River. With its contemporary, neutral décor and breathtaking river views, Harbour View blends a rich luxurious feel with the natural beauty of a waterfront setting. If you’re looking to put on an elegant affair with a guest count of 10 to 300 guests, you’ve come to the right place.

A gorgeous wedding venue just minutes from Annapolis. The Golf Club at South River is a unique golf club and wedding venue located in Edgewater, Maryland. Located just minutes from Annapolis, The Golf Club at South River offers a perfect blend of rustic and modern elements set against a lush and scenic backdrop. From the spectacular views to the lavish furnishings, The Golf Club at South River could be the perfect place to celebrate your dream wedding day. Our catering team, offers custom menu selections for plated, buffet and culinary station style events. Enjoy a signature cocktail, hors d’oeuvres, creative culinary stations, a rustic-style buffet, or an elegant plated affair at your reception. We look forward to guiding you through the process of planning your once in a lifetime occasion!

An elegant yet comfortable venue to host all of your wedding festivities. Your bridal party is welcome to begin preparations early by relaxing and getting ready in our luxurious bridal suite and the men in the groom's cabin. You can have your ceremony in front of our majestic barn, on the first floor of the refurbished interior, or the top floor overlooking the gorgeous rolling hills. Events flow beautifully into a patio cocktail hour space beside our rustic chic bar area and courtyard. The party moves toward the barn for the celebration continues with dinner and dancing the night away.

Swan Point is a boutique waterfront venue designed for intimate weddings with 50 or fewer guests. Set along the Occoquan River, our gazebo and natural surroundings create a peaceful, romantic backdrop. We specialize in small celebrations that feel personal and elegant—never crowded or rushed. Our space is ideal for couples who value simplicity, aesthetics, and a relaxed experience. Please note: we do not accommodate events above 50 guests.

Hemlock Farm is the perfect rustic venue for a beautiful summer wedding. Known for its stunning weddings and annual Christmas tree selection, this charming farm offers a warm and welcoming atmosphere. Weddings take place in front of the picturesque red barn, surrounded by family and close friends. Hemlock Farm also offers the freshest fir Christmas trees and greenery, making it a family-friendly destination year-round. Celebrate your special day in a setting that combines rustic charm with heartfelt hospitality at Hemlock Farm.

Our goal is to provide a million dollar outside wedding site at an affordable price AND treat every bride like she is our own daughter. In the 1950’s thru the mid 1970’s the site was known as Motts Run Landing, which provided access to the Rappahannock River for families, boaters and fishermen by day and a local lovers lane by night. In 1979 Gene & Linda Clore purchased this 2 ½ acre slice of heaven and dedicated their lives to the fun and pleasure of those who wished to enjoy the Rappahannock and Rapidan rivers by canoe. Because of it’s natural beauty a friend of the family, in 1993, requested to have their wedding overlooking the river. Thus was the inception of Riverside Weddings. After a few years of one or two weddings per year with family and friends (and friends telling friends about our enchanting spot to get married) it was obvious that we had become “Riverside Weddings by Clore”

Imagine exchanging vows with the Chesapeake Bay as your backdrop, surrounded by lush landscapes and the charm of a living shoreline. The Annapolis Maritime Museum offers a unique and picturesque setting in America’s Sailing Capital, where you can host your special day right on the water. Enjoy stunning views, an affordable venue, and a true taste of Annapolis. The Annapolis Maritime Museum & Park boasts 2 uniquely charming waterfront wedding venues. The Maritime Museum: located in the Eastport neighborhood of Annapolis, the former McNasby’s Oyster Company building offers outdoor ceremony and indoor reception space with a uniquely Chesapeake Bay vibe. The Park Pavilion: located within our 12-acre park campus along the scenic shores of Back Creek, offers a rustic stone amphitheater ceremony space with an open-air Pavilion reception, that includes a working stone fireplace. The Annapolis Maritime Museum is the coastal venue of your dreams- where history meets the harbor.

At Top of the Town, your wedding is more than an event—it’s an experience your guests will remember long after the night ends. Perched above Arlington, our penthouse venue offers sweeping, unobstructed views of Washington, DC—from the Capitol and Washington Monument to the Lincoln Memorial and beyond. As the sun sets and the city lights begin to glow, the space transforms into something truly unforgettable. Designed for couples seeking a unique and elevated experience, Top of the Town features both indoor and outdoor spaces for your ceremony, cocktail hour, and reception to flow seamlessly from one moment to the next. We comfortably accommodate up to 180 guests cocktail-style and 150 seated. We provide the essentials—including tables, chairs, a spacious dance floor, and a private outdoor terrace—while giving you the flexibility to bring in the catering and personal touches that reflect your vision. We’d love to welcome you for a tour and show you the view in person.

Step foot in our luxury hotel in Washington D.C. and discover an urban resort located along the banks of the Potomac River. Here, you’ll uncover a hotel unlike anything in Washington D.C. — a place where modern design blends with an iconic landmark to redefine luxury. The Watergate Hotel's flowing avant-garde architecture was designed by Luigi Moretti to emulate the mighty Potomac, and its stunning new Ron Arad-designed interior lives up to the building's original elegance. Complementing the hotel's new, modern feel are the retro-chic staff uniforms, made by Mad Men costume designer Janie Bryant. The Watergate Hotel takes classic elegance and bold mid-century modern design and adds all of the extravagance and warmth of contemporary luxury. This one-of-a-kind hotel pays tribute to its own storied past, while paving the way for a new chapter to be written.

Please send all inquiries directly through our website. Stafford Stables is conveniently located an hour from DC and Richmond. This Virginia venue offers the perfect blend of modern facilities, rustic charm, and majestic horses. Featuring both indoor and outdoor spaces for intimate to grand events, it's a truly unique equestrian setting.

Welcome to Oasis in scenic Stafford County, your exclusive Virginia wedding and event get away Tucked away off the beaten path near Stafford, Virginia is a hidden gem, Oasis Weddings. While offering seclusion and privacy, we are conveniently located on the I-95 corridor, an hour from both Richmond, Virginia and Washington DC The Oasis sits atop a knoll with expansive views of open space, lush landscaping and mature trees that ring the beautiful setting. A standout among small wedding venues and outdoor wedding venues, we cater to the needs of an exclusive, demanding clientele and their guests.

Wildflower Estate is where luxury meets love. Offering both venue-only and all-inclusive packages, our Maryland Eastern Shore estate pairs chic design with lush landscapes. Whether you want a fully planned wedding or the freedom to craft your own, we provide the perfect backdrop for a celebration that’s effortlessly stylish and uniquely yours.

Nestled within over 100 acres, the heart of the campus is an early eighteenth century home surrounded by a collection of inviting living and entertaining spaces. A relaxed atmosphere with natural, organic elements and a modern edge, Seven Springs is the perfect backdrop for a wedding weekend getaway, farm to table dinner celebrations, and other collaborative community events.

There is a special sort of feeling that being here at the farm brings, a calm and peaceful energy about the property. Maybe it is the history, there is comfort in knowing the original farmhouse, which sits at the center of the property, has stood for over two centuries. Maybe its the rustic beauty of the big white barn, that was built by farmers as a dairy barn in 1920. This little slice of heaven has been a part of so many families who lived and worked this land over the past 250 years. Come and see for yourself.

Dawn On the Chesapeake is an exquisite outdoor venue designed for elegant events. Nestled along the waterfront, our location exudes intimate and romantic charm, perfectly complemented by a stunning Mediterranean-style mansion that serves as both a picturesque backdrop and the home for our spacious getting-ready suites.

At Arks Landing we can help you plan your event from start to finish. With over 30 years of experience planning and holding events here, we have established relationships with any and all the vendors you will need for your big day! From tent & furniture rental, to caterers, bartenders, deejay's, & photographers, we have the connections to make planning easy and your special day the event of a lifetime! Do you want to arrive by horse drawn carriage? We can do it! Do you want to arrive or depart by boat? We can do it! Whatever you imagine to make your event the most memorable, we can help make your dream possible!

Monroe Bay Vineyard is located on the water near Colonial Beach on the original birthplace Farm of our 5th President James Monroe. We have secluded and tranquil waterfront land to plan your perfect day. We have a large, unique barn made of natural, recycled materials of strawbales for insulation and recycled wine bottles for light and design. You no longer see the strawbales in the wall as they have been covered with a hydraulic lime the same material castles in France for hundreds of years have been made from. The inside is a museum quality white lime finish with unique curves with sun shining through the patterned wine bottle walls to give a unique backdrop.

Robin Hill Farm and Vineyards offers a rustic yet elegant setting for weddings, surrounded by lush vineyards and scenic countryside. The venue's charming farmhouse and expansive grounds provide a picturesque backdrop for both ceremonies and receptions. With personalized service and attention to detail, Robin Hill Farm ensures a memorable celebration. Ideal for couples seeking a tranquil and natural environment, this venue captures the essence of rustic charm and sophistication.