Outdoor eating in Leonardtown, Maryland

Olde Town Pub is a cozy and inviting bar, food, and restaurant located at 22785 Washington Street in Leonardtown, Maryland. This charming establishment offers a laid-back atmosphere where patrons can enjoy delicious food, refreshing drinks, and good company. Whether you're looking to grab a bite to eat, have a few drinks with friends, or catch a game on TV, Olde Town Pub has something for everyone. With its friendly staff and welcoming ambiance, it's the perfect spot to unwind and relax in the heart of Leonardtown.

Patuxent Adventure Center Paddle Sports is a store located at 23190 Newtowne Neck Road, Leonardtown, Maryland, United States. They offer SUP, single kayak, and tandem kayak rentals for customers to explore the marinas, wildlife, and beautiful Solomons Island from the water. At their State Hwy 326 location in Leonardtown, customers can enjoy calm open water paddling and spot plenty of wildlife. The historic downtown Leonardtown location offers a chance to paddle and grab a meal afterwards. For a more scenic paddle experience, customers can rent single and tandem kayaks at the McIntosh Run location, where they can paddle through the trees and navigate through shallow spots. It is recommended to check the tidal chart and paddle at higher tide times to avoid leaving the boat. Customers are advised to bring water, a hat, sunscreen, and water shoes for their paddle adventure, with personal floatation devices and paddles provided by the center. Visit Patuxent Adventure Center Paddle Sports for a memorable paddling experience in Maryland.

Checker's Well is a cozy and welcoming restaurant located at 3002 Leonardtown Road in Waldorf, Maryland. Known for its delicious comfort food and friendly atmosphere, Checker's Well is the perfect spot for a casual meal with friends or family. Whether you're craving a juicy burger, crispy fries, or a refreshing milkshake, Checker's Well has something for everyone. Stop by and enjoy a satisfying meal in a laid-back setting at this popular eatery in Waldorf.