The 5 best wedding venues in Leonardtown, ranked and compared

The Fenwick Inn is a boutique wedding and event venue in the Arts & Entertainment District of downtown Leonardtown, Maryland, housed in a 1933 home that the O'Connor family purchased in 1999 and reimagined into a personalized event space. The property combines a historic main floor, an upstairs bridal suite with two bathrooms, the newly enclosed Booker Pavilion with greenery-draped chandeliers, a dedicated bar, and outdoor grounds with an evergreen-lined path and shaded courtyard. The venue accommodates up to 100 seated or 120 standing guests, and a 4-hour wedding rental is $5,000. Founder and lead planner Donna O'Connor leads a family team (Danny, Noelle, Bobby Jo, Paige and Sarah) that provides wedding planning, day-of coordination, and personalized beverage service, while allowing outside catering and vendors.

Port of Leonardtown Winery is a working winery and tasting room in Leonardtown, Maryland (St. Mary's County) open seven days a week with live music on weekends. The property hosts small weddings and receptions, bridal/baby showers, birthday celebrations and corporate dinners in its tasting room, covered heated patio, outdoor patio and enclosed gazebo. With all spaces combined the venue can host 120-150 guests (about 80 in winter), and the gazebo seats up to 18 for private gatherings. Due to licensing, outside alcoholic beverages are not allowed but outside food (potluck or professional catering) is permitted, and the on-site event coordinator Sharon is repeatedly praised in reviews. Gazebo rentals are $35/hour or $150/day; tasting-room rentals are priced on inquiry.

Jubilee Farm & Vineyard is a historic waterfront wedding venue in Leonardtown, Maryland, set on a private peninsula with formal gardens, a working vineyard and a bluff overlooking Blake Creek and the Potomac River. Ceremonies are held on the waterside bluff (also called the west lawn) and receptions take place inside the Amish-built Winery Barn, with cocktail hour in the vineyard courtyard. Couples get separate getting-ready spaces: the Guest Cottage for the bridal party and the Garaj Mahal loft (Groom's Quarters) adjacent to the pond. In-house bar service is provided via sister farm Woodlawn at $24/adult for wine and beer or $30/adult for top-shelf open bar for four hours. White padded resin chairs are set up for the ceremony, the venue maintains a preferred-vendor list, allows outside caterers, and requires $1,000,000 wedding liability insurance.

Olde Breton Inn is a historic waterfront mansion atop Society Hill in Leonardtown, St. Mary's County, Maryland, family-owned by the Bailey family for over 30 years (40 in 2027). Originally built as early as 1670 and operated as a private home, restaurant and country club, the Inn now hosts weddings, corporate events and special occasions overlooking Breton Bay, St. Clements Bay and the Potomac River. The venue seats up to 140 guests indoors with the option to add an outdoor tent for larger gatherings, and features a signature gazebo for ceremonies, a panoramic dining room with sliding glass walls, a 2,000 sq ft wraparound waterfront deck (wheelchair accessible, with heaters), a bridal suite and ample free parking. Catering is offered exclusively by Bailey's Catering, a St. Mary's County staple for 50+ years.

The Front Porch is a Southern Coastal restaurant inside the historic Sterling House in downtown Leonardtown, Maryland, that also hosts weddings, rehearsal dinners and private receptions. Spread across two floors with original hardwood floors, period molding, fireplaces and a gracious wrap-around porch, the venue offers five private dining rooms, including the Balcony (18), Big Room (60), Vault (12), Wine Room (25), plus the outdoor Deck and Porch, and can accommodate up to 200 guests overall. Catering is provided in-house with set brunch, lunch and supper menus that can be personalized, with party pricing roughly $950–$2,000 for 50-guest events; non-alcoholic beverages are included. The restaurant serves Southern fare, craft beer and clever cocktails, has full ADA accessibility and on-site free parking.