Things To Do
Main Street Gettysburg
Downtown Gettysburg is a charming small-town hub packed with dining, drinks, and fun activities that go beyond the battlefield. The town’s streets are lined with boutique restaurants, craft breweries, and cozy taverns, making it easy to spend an afternoon sampling local flavors or enjoying a lively evening out. Favorites include The Pub & Restaurant for hearty fare and drinks, Blue & Gray Bar & Grill for casual bites, and local breweries like Gettysburg Brewing Company for craft beer enthusiasts. Cunningham Falls and nearby cycling or walking trails offer a way to enjoy the beautiful Pennsylvania landscape, or you can take a guided Segway or trolley tour for a more relaxed way to explore the area. At night, the downtown bars and taverns come alive with live music and a friendly, welcoming vibe that makes it easy to mingle with locals and visitors alike.
Downtown Frederick
Downtown Frederick has historic streets are lined with boutique shops, art galleries, and local eateries, perfect for leisurely strolls or picking up a unique gift to remember your visit. Enjoy a relaxed evening by Carroll Creek at restaurants like The Wine Kitchen on the Creek, or enjoy more fine dining at restaurants such as The Tasting Room or Dutches Daughter. For a more casual night out, check out Frederick Social, a fun self-pour taphouse featuring local craft beers and cocktails, or Rak Brewery for more lively vibes. Catch a live performance at the Weinberg Center for the Arts or explore local artwork at the Delaplaine Arts Center. If your visit falls on a First Saturday, downtown comes alive with late-night shopping, gallery exhibits, and food tastings — a perfect way to experience the city’s energy. You can also enjoy the scenic Carroll Creek Linear Park or stroll through the beautiful and calm Baker Park.
Inner Harbor
Baltimore’s Inner Harbor is a bustling waterfront destination that perfectly blends dining, nightlife, and family-friendly attractions. The harbor is lined with restaurants, bars, and patios where you can sip cocktails, enjoy local craft beers, or feast on fresh seafood with stunning views of the water. Popular spots include Phillips Seafood, The Rusty Scupper (water taxi accessible), and McCormick & Schmick’s, while trendy bars and breweries like Cross Street Market and Power Plant Live! offer lively nightlife. Hop on a harbor cruise, try paddleboarding, or take a sightseeing tour by water taxi. A must-see is the National Aquarium, where visitors can explore immersive exhibits featuring sharks, tropical fish, and playful penguins. Shopping enthusiasts will enjoy Harborplace & The Gallery, with a mix of boutiques, specialty stores, and souvenir shops, making it easy to pick up something unique while taking in the waterfront views.
Downtown Annapolis
Downtown Annapolis is a waterfront location for those who love good food, drinks, and fun on the water. Start with City Dock, where you can grab a cocktail or local craft beer at one of the harbor-front bars while watching sailboats drift by. The dining scene is a standout — fresh seafood is a must, with favorites like Choptank, Boatyard Bar & Grill, or casual bites at Chick & Ruth’s Delly. For more upscale experiences, many waterfront restaurants serve perfectly paired wine and local Chesapeake flavors. Main Street and the surrounding streets offer a mix of lively bars, pubs, and live music venues where the evening buzz is just as rich as the food. If your group loves water adventures, try kayaking, paddleboarding, or a sailing tour right from the harbor. Whether it’s cocktails at sunset, seafood feasts, a harbor cruise, or shopping, downtown Annapolis balances the charm of a historic city with all the excitement of dining, bars, and water fun.