Herrington Harbour Sailing Association

05/19/2026

Our teams are gearing up for the Annapolis2Bermuda race which starts on June 5! This year we have 4 member boats racing!
Allegiant Sailing (Albert Bossar and Maryline Bossar)
Adeline (Miguel Serrano)
Huzzah (Jason Woodson)
Widow Maker (Russ Matijevich)
And countless members crewing on these and other boats (post in the comments to call out who you are and which boat you're on!). Watch too for our friends on Bay Retriever.

Want to come support the racers and see the start? Check out the start week programming at: https://www.bermudaoceanrace.com/annapolis-events

For a special treat, the Schooner Woodwind: Annapolis Sailing Cruises will be bringing people out to watch the start. Isn't Chesapeake Bay sailing awesome?

12:00 – 14:00 Race Start live streamed and Watch Party at EYC Aft Deck12:30 – 15:00 “A2B Start Watch Cruise”: Get front row to the start of the race from the Woodwind schooner! Register here

05/14/2026

Join our 2026 Women's Regatta prep call tonight at 730!

Info and registration: https://hhsa.org/content.aspx?page_id=4091&club_id=8237&item_id=2906777

05/11/2026

Women sailors, don't forget to register for this Thursday's prep seminar for the 2026 HHSA Women's Regatta! Past skippers and crew will tell you how much fun it is - and new skippers and crew this is a great chance to connect and form team!
Thursday May 14 at 730pm on Zoom. Register at https://hhsa.org/content.aspx?page_id=4091&club_id=8237&item_id=2906777
Women's Regatta is July 11. See you there! HHSA.org

04/29/2026

It's on again!! All women, all day, all sailing. The 2026 HHSA Women's Regatta will be held on July 11, 2026. The regatta page is live and we are starting our prep seminars. The first one will be on May 14 at 730pm. Come and meet past and hopeful skippers and crew and learn about this great event. Seminar registration is at: https://hhsa.org/content.aspx?page_id=4091&club_id=8237&item_id=2906777. We can't wait to see you!

04/27/2026

Join us for the HHSA Shakedown Cruise, May 2–3! This is the perfect chance to get back on the water, test your systems, build confidence, and enjoy an easygoing weekend with great company. Whether you’re shaking off winter cobwebs or just here for the fun, it’s all about getting out there together. See you on the Bay!
Info and registration at: https://hhsa.org/content.aspx?page_id=4091&club_id=8237&item_id=2906775

04/26/2026

Some of the awesome women at our Women Underway Boat Show Social today! Check out our upcoming programming to get involved: HHSA.org

04/26/2026

Women sailors! Hope to see you for our Women Underway Boat Show Social today! See you at 1030 at Annapolis Marketplace. All welcome.

04/24/2026

It's spring boat show weekend!! Come out and see us (members, sign up to volunteer and get your entry discount). Women sailors (you don't need to be an HHSA member) register for our Women Underway Social at: https://hhsa.org/content.aspx?page_id=4091&club_id=8237&item_id=2906638

04/05/2026

Spring is here, and there’s no better way to start the season than together! Join us for a members breakfast as we reconnect with familiar faces, welcome new ones, and look ahead to the season on the water. Whether you’ve been part of our community for years or are just getting involved, this is your invitation to pull up a chair. Good conversation, shared stories, and a chance to build the kind of connections that make this group special. ⛵🫶

✅Please remember to RSVP so we can plan accordingly. We’d love to see you there!

03/24/2026

Past Commodore Matt Smith and his girlfriend Lee Tangonan will be navigating the Great Loop this year aboard the new version of "Snacktime"…a 53’ powerboat! If you’re interested in following along, check them out at www.sailingsnacktime.com and subscribe to their YouTube channel for weekly videos. Safe travels Matt and Lee!!