What are the Annapolis Boat Shows?

Beginning with the first-ever in-water sailboat show in 1970, for over fifty years, the Annapolis Boat Shows have produced in-water sail and powerboat shows where boaters may board the latest boat models, research and purchase boating equipment, foul weather gear, electronics, nautical education, charters, and everything else a boater or boat owner needs. 

The United States Powerboat Show features everything from luxurious motor yachts to trawlers, high-performance boats, and offshore fishing vessels. There are also family cruisers, center consoles, and inflatable and trailerable powerboats. Vendors' tents line the waterways, selling everything powerboat enthusiasts could dream of and offering boating lessons, rentals, and more. 

Annapolis Powerboat Show

October 8-11, 2026

What To Expect

⛵ Premiering Boats: See the world premiere of the Knysna 550 and North American debuts from the Jeanneau Sun Odyssey 455 and Vaan R4, plus hundreds of sailboats from daysailers to bluewater cruisers.

🎓 Learn the Ropes: Take part in hands-on sailing workshops, free seminars, or Cruisers University, featuring more than 80 classes taught by leading instructors.

⚓ Faces You Follow: Meet the sailing personalities you follow online at Cruisers Creating Content and explore new exhibitors like the Endurance Weather Center and Backstay Offshore logbooks.

🦆 Fun for the Whole Crew: Hunt for Dockside Ducks, take part in the EWE Spirit scavenger hunt, enjoy the College Sailing Reunion happy hour, or grab a drink at the No Wake Zone.

Annapolis Sailboat Show

October 15-18, 2026

What to Expect

⛵ A Fresh New Layout: Explore expanded tents, reimagined spaces, and four new bars.

🚤 350+ Boats to Discover: See world premieres and exciting new-to-show models.

⚓ Sea Trials Available: Qualified buyers can test select boats on the water.

🎓 Learn from the Experts: Attend free seminars or hands-on boating courses.

🍻 Sip & Relax: Enjoy the No Wake Zone or explore downtown Annapolis dining.

🎨 Family-Friendly Fun: Crafts, games, boatbuilding, and prizes for kids.

Where to Dine & Drink

Chances are many of your fondest memories are of good times spent with family and friends over a great meal.

🍳 Chick & Ruth's Delly - A beloved Annapolis tradition for more than 50 years, Chick & Ruth's Delly serves up fresh, made-from-scratch comfort food, Maryland favorites, and legendary hospitality from breakfast through dinner.

🥞 Iron Rooster - Whether you're looking for breakfast all day, lunch, supper or drinks, at Iron Rooster you'll find a new twist on traditional comfort food, legendary hospitality, and a real sense of community.

🥐 Bread and Butter Kitchen - Bread and Butter Kitchen is a cafe in Eastport, Maryland serving breakfast and lunch daily.

🥓 Eastport Kitchen - A neighborhood spot in Eastport, Eastport Kitchen serves scratch-made breakfast and lunch favorites, from signature sandwiches and Maryland crab soup to crispy fries, all with a warm, community-focused atmosphere.

🥯 Bitty & Beau's Coffee - Bitty & Beau’s is a business dedicated to hiring people with intellectual or developmental disabilities. Serving coffee, tea, and bakery treats.

🦀 Dock Street Bar & Grill - Dock Street features Chesapeake Bay cuisine, superior night life and a full menu for everyone.

🌮 Armada Dockside Cantina - Armada is energizing the Annapolis waterfront dining scene with bold and vibrant flavors.

🦪 McGarvey's Saloon & Oyster Bar - An Annapolis staple for over 45 years, McGarvey's offers the fresh seafood, a friendly atmosphere, and a memorable experience in the heart of historic downtown Annapolis.

🍝 Osteria 177 - Utilizing the fresh organic ingredients, Osteria 177 specializes in Fresh Italian Seafood, Chops, Pasta, and Seasonal Game.

🍅 Marmo - An Italian-inspired chophouse serving bold flavors and timeless dishes.

🍨 The Red Bean - Offers a vibrant and daring experience with custom ice cream flavors, bold espresso creations, and whole leaf teas.

🍷 Vin 909 Winecafe - Housed in a charming Eastport cottage, VIN 909 Winecafé is a local spot for wood-fired pizzas, seasonal dishes, and thoughtfully curated wine and craft beer.

🍔 The Admiral's Cup - Classic bar favorites done right. From saucy or dry rubbed wings and shareable pizzas to crave-worthy handhelds and comfort-driven bar bites.

🦀 Boatyard Bar & Grill - The Boatyard’s “all killer, no filler” crab cakes are famous all the way to the White House and beyond.

🍽️ DRY 85 - A modern industrial take on a Prohibition-era speakeasy. The back alley garage where someone today would sneak a bourbon, beer or gourmet comfort food meal.

🥩 Lewnes' Steakhouse - The Lewnes family has been serving fine food at this location since 1921. Lewnes’ Steakhouse holds the distinction of being the first Annapolis restaurant to feature U.S. Prime Steaks. 

🦀 Carrol's Creek Cafe - Waterfront restaurant with a stunning view of the historic skyline and harbor. Features regional American dishes with an emphasis on seafood. Popular Sunday brunch spot and beautiful outside dining.

🌭 Pip's Dock Street Dogs - Offers classic Nathan's all beef hot dogs, cheese steaks, fries, and freshly made 1/4 lb. burgers.

🍕 Fox's Den - Hidden in plain sight, step into Fox’s Den, your go-to spot for good vibes, great food, and a laid-back atmosphere. Enjoy wood-fire pizzas, small plates, and craft beers.

🍽️ Davis' Pub - True to its founder, Davis’ Pub has stayed a local, neighborhood joint with good, affordable food.

🍦 Annapolis Ice Cream Company - The ONLY store-made ice cream in Historic Annapolis. 

🥥 Rumhouse - Offers luxe interpretations of Caribbean cuisine alongside an extensive rum collection in the Eastport neighborhood of Annapolis.

Where to Drop Anchor

Drop anchor near the heart of the festivities, whether you're drawn to historic charm, modern comfort, or a touch of luxury