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Who We Are

The Annapolis Watersports Festival was created by a partnership between Capital SUP and the Annapolis Sailing School. The mission of the event is to bring together the local paddling and sailing communities & businesses for a fun day of maritime activities in support of the Live Water Foundation. A day filled with paddling and sailing, races & activities, outdoor wellness, live music, local vendor area, best of Annapolis food & beverages, beach games, and more! The Annapolis Watersports Festival is a family-friendly event that will have something fun for everyone!

Event Date Change

The Annapolis Watersports Festival is “Springing to Fall”. The response has been so positive for our event that we want to take the summer to plan expanded offerings and capacity. The new date is:

 Saturday, September 15th.

BUT for those anxious to get on & in the water, the Annapolis Sailing School will be offering the perfect experience:

Sail Into Summer

Saturday, May 26

Join the Annapolis Sailing School for sailing, stand up paddleboarding and kayaking, as well as food, music, nautical lectures, and games such as beach volleyball shoreside. There is something for everyone- adults, children, novices, and experts alike on the beaches and docks at 7001 Bembe Beach location.  To get more details on this Memorial Day weekend activity go to the event Facebook page Sail Into Summer and stay up to date by following Annapolis Sailing School on Facebook or their website.

About the Live Water Foundation

Established in 2016, The Live Water Foundation was formed to support the signature give-back initiatives of the team at Capital SUP and to lead the advocacy of water sports activities that will improve the well-being of our communities. The Mission of the Live Water Foundation is to inspire and empower the people and organizations we work with and facilitate programs to improve the health, wellness, and environment of our communities.  The Live Water Foundation currently supports three initiatives within the Veteran community, underprivileged and disabled youth, and promoting clean waterways. Our programs include: the Wai Koa Program, an adaptive paddling program for physically and mentally disabled Veterans; the Watermen’s Club, which inspires underprivileged and disabled youth to become future leaders through a watersports mentorship program; and the Oyster Recovery Program, which oversees and maintains 50 oyster cages off the docks of the South Annapolis Yacht Centre. In addition to programmatic support, the Live Water team aspires to create “Positive Vibes” within the Veteran community, inspire underprivileged and disabled youth to become future leaders, to be champions in the enhancement of the waterways in which we paddle, and to inspire a lifestyle of health and wellness through watersports activities.

Festival Activities

  • Paddlesports Demo Area. Local vendors include Evolve SUP, Solace SUP, East of Maui, Annapolis Dragon Boat Club, and more! Included in the event registration.
  • Sailing experiences. The Annapolis Sailing School has opened their fleet of sailing vessels for you to demo! Included in the event registration.
  • By Land & By Water Yoga Class sponsored by Lululemon. Led by Annapolis’s favorite Yogi’s, take the class on the floating docks or on stand up paddleboards. Included in event registration.
  • Waterman’s Race sponsored by Koons Toyota. A fun and competitive multi-craft race designed for people who love being on the water.
  • Live Music. Pressing Strings and Proverbs Roots Rock Reggae Band will be jamming on stage.
  • Tiki Bar sponsored by Red Stripe Beer Co.
  • Beach games & leisure area.
  • Local vendors. Showcasing the best of what Annapolis has to offer! Includes RASA Juice Shop, Cumberstone Ice Pops, The Painted Mermaid, Windjammer Workshop, River Sea Chocolates, and more!


Event registration goes live Monday, April 2. We are using a local ticket registration platform called What’s Up Tix. The same team that produces What’s Up Magazine publications.


  • Adult: $50
  • Teens (13-17): $25
  • Kids (12 & Under): Free
  • Included in the registration is:
    • Swag bag, access to paddlesports demo area, sailing experiences, yoga class, lunch, and drink tickets (adult only)

Sponsors & Vendors

We are actively taking on Sponsors & Vendors to be apart of the 1st Annual Annapolis Watersports Festival. The event is geared towards those living an active and outdoor lifestyle but will be a family-friendly event with things to do for all ages. The core of the event attendees will come from the Eastport and Annapolis area. Our reach will extend all over Anne Arundel County as well as into the cities of Baltimore and Washington DC.

For sponsorship and vendor inquiries, please email [email protected]

Looking forward to seeing you in both Spring and Fall!

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