Yappy Hour
Bring your best furry friend and join Capital SUP for Yappy Hour, Annapolis’ favorite dog-friendly paddleboarding event! This fun and relaxed group paddle invites dogs and their humans to hit the …
Puppy Plunge
The SPCA of Anne Arundel County’s annual Puppy Plunge is officially returning on Sunday, August 23, 2026, and we can’t wait to spend another unforgettable day at the beach with our amazing community …
Blue Angels Paddle
Experience the excitement of the 2026 Blue Angels Flotilla Paddle with Capital SUP in Annapolis, Maryland, the ultimate way to watch the U.S. Navy’s Blue Angels Air Show from the water. This one-of-a-kind paddleboarding and kayaking event offers …
Full Moon Paddle
Experience the Chesapeake Bay in a whole new way with Capital SUP’s Full Moon Paddle in Annapolis, Maryland. Glide across calm, moonlit waters and take in the peaceful glow of …
Antique & Classic Boat Festival and Coastal Arts Fair
The 38th Antique & Classic Boat Festival and Coastal Arts Fair will be at the Chesapeake Bay Maritime Museum from June 19-21, inviting guests to take a step back in …
The Santa Maria Cup
The Santa Maria Cup is one of the premier women’s match racing regattas in the world. Hosted annually by Eastport Yacht Club in Annapolis, Maryland, the event brings together top …
Annapolis Powerboat Show
October brings the transformation of Ego Alley and Annapolis Harbor into a boater’s dream, as floating docks create a temporary marina showcasing new and premiering boats and the latest in …
Bay Bridge Boat Show
The Bay Bridge Boat Show at Safe Harbor Narrows Point offers an immediate connection to the Chesapeake Bay boating lifestyle. Non-boaters can climb aboard boats, walk the docks, and explore …
Annapolis Spring Sailboat Show
The Annapolis Spring Sailboat Show provides a local, fun, and accessible entry point to the sailing lifestyle. Located in the heart of America’s sailing capital, the event offers opportunities to …
Polar Bear Plunge with Rams Head
Join our team for the 30th annual Polar Bear Plunge. Since 2008, Rams Head has been a proud supporter of Special Olympics Maryland’s mission to raise funds and awareness for …