Explore Annapolis’s historic streets, charming local shops, and lively food and bar scene while you’re in town. The Annapolis Sailboat Show will be downtown from October 15–18 and is a fun event to check out—please note that traffic and crowds will be heavier during this time. Restaurant reservations are highly recommended. Some of the bride’s favorite spots include Boatyard Bar & Grill, Choptank, Davis’ Pub, Forward Brewing, Fox’s Den, Preserve, The Admiral's Cup, and The Parley Room.
Cozy Italian in Stevensville—ideal for a pasta-and-wine night
Waterfront dining with Chesapeake classics and weekend live music
Cozy waterfront winery with tastings and sweeping Bay views
A relaxed craft brewery featuring local flavors and seasonal brews
Known for fresh Maryland seafood, steamed crabs, and stunning views of the Kent Narrows in a relaxed, coastal setting
Farm-to-table dining with local seafood, craft cocktails, and rustic lodge vibes inside The Inn at Chesapeake Bay Beach Club
Dockside dining with panoramic Bay views, fresh seafood, and a creative drink menu
Waterfront dock bar serving up crab classics, cold cocktails, and live music
A cozy café and market at The Inn offering breakfast, lunch, smoothies, coffee, and easy grab-and-go bites
Sandy beach, fishing pier, hiking trails, and dog‑friendly areas—just a few minutes from the venue
Perfect for biking, walking, or spotting wildlife along the scenic rail‑trail