US Sailboat Show

The United States Sailboat Show takes over the Annapolis Harbor October 4th through the 8th, followed by the United States Powerboat Show

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Debuting in 1970, the Annapolis Boat Shows have wowed boating enthusiasts for over forty years. With close to 150,000 attendees from around the world flocking to Annapolis for the world's largest in-water boat shows, there's no better place to catch a glimpse of cutting-edge designs and sleek classics than right here in the Sailing Capital of America. Spend the day hopping from one vessel to another before stocking up on sailing essentials from the many vendors in attendance, offering everything from high-tech navigational equipment to outboard motors. Purchase your tickets today for the U.S. Sailboat and Powerboat Shows in Historic Annapolis.

Sailboat Show

The United States Sailboat Show offers attendees the chance to climb aboard some of the sea's most extraordinary wind-powered boats. Recognized worldwide as the premier sailing showcase, the United States Sailboat Show treats visitors to some of the world's finest vessels and state-of-the-art equipment. Hop on aboard any boat that catches your attention. Browse through the vendors' tents, stocking up on the latest sailing gear.

There's no better way to get your sailing fix than at the U.S. Sailboat Show, October 4th through the 8th, on the historic Annapolis waterfront. Learn more about the Sailboat Show.

Make a Weekend Out of It 

Experience the wonderful events, activities, restaurants, and more happening around the area to keep your weekend going!

Fun Events
Sin & Secrets at London Town: Pirates, murder, and scandal aplenty await you on this adults-only, after-hours tour of Historic London Town and Gardens. Walk the streets of the long dead seaport, discovering its more salacious stories. Oct. 5 – Oct. 8 at 8:00 p.m.

Maryland Renaissance Festival: Take a stroll through a 16th-century village, complete with King Henry VIII and his court. Enjoy more than 250 performers on ten stages, 130 craft shops, 42 food and beverage emporiums and a host of games and attractions. Open Saturday & Sunday, 10:00 am – 7:00 pm.

Fall Festivals: Celebrate the unique culture and cuisine of Annapolis and Anne Arundel County during a fall festival. The Greenstreet Gardens Fall Festival and Homestead Gardens’ Annual Fall Festival are in full swing each weekend throughout the month of October, offering families everything from fun activities like corn mazes and hayrides to pumpkin carving/painting and fresh, seasonal vegetables.       

Working the Water Exhibit: A publication documenting the Chesapeake Bay’s contribution to the seafood industry by local photographer, Jay Fleming. With over 300 photographs of nearly every fishery in Maryland and Virginia, Jay sheds light on the lives of those individuals whose livelihoods is dependent on the Bay.On display at Maryland Hall for the Creative Arts daily from 9:00 am – 5:00 pm.

Walking Tours: Open your eyes to history, cultural heritage, maritime life, and scenic beauty when you take one of the many tours offered in the historic district. 

Explore the Arts
From solo shows to musical performances and videos of art to artistic storytelling, Annapolis has something for everyone to enjoy. While you’re here, browse through the city’s 20-plus art galleries or experience a show at one of the area’s world-class theatre’s - like “The Comedy of Errors” presented by the Annapolis Shakespeare Company.

Where to Eat
From small plate lounges to local favorites and tasty hidden specialties, Annapolis has a long list of delicious restaurants to choose from. Experience the perfect brunch spots, enjoy some fresh oysters, or take a trip by car or boat to South County for a bite to eat. Visit Foodie Annapolis for some more great dining suggestions.

Evening Entertainment       
Annapolis is known for its live music scene. As you walk through the historic streets of Annapolis, you are likely to hear the sounds of local favorites wafting out of local pubs and restaurants. Or, hop over to LIVE! Casino & Hotel. Whether its gaming, dining, or live music – you’ll find it at LIVE!