Southern Maryland Sailing Association

Welcome to Southern Maryland Sailing Association (SMSA) on the web.

SMSA was founded in 1972 as a member-run social club by a group of like-minded sailors interested in racing, cruising, and just spending time with fellow sailors.

Since then, SMSA has grown to more than 175 memberships and has continued to offer a large variety of activities for its members and the community.

SMSA offers comprehensive racing, cruising, junior & adult sail training, education, and social activities both on-shore and on the water that allow members to enjoy the sport of sailing through a variety of venues throughout the year.

Our goal is to continue to be the premiere sailing venue in the Southern Maryland and mid-Chesapeake Bay region.

We are ideally located in Solomons, MD, near some of the finest cruising waters of the Chesapeake Bay.

We look forward to your first or frequent return visits with us.

Candidate Slate for 2026 Officers and Directors

Click below for Bios and pictures of your volunteers.
All nominations and self nominations must be received and acknowledged by 5pm on October 3rd, 2025.

Click Here for more details.

Annual Crab Feast

Saturday, October 4th, 5:30pm
Tickets: $30 ($15 kids 12 and under; Ages 5 and under FREE)
Includes sides and dessert.
Non-seafood entrees also available.
Purchase tickets by 28 Sept. Limited tickets available after 28 Sept.

Event Page

Smallboat Fall Invitational Regatta

Are you ready to sail? Get ready for the SMSA Fall Invitational Regatta to be held October 4th and 5th, 2025.

Chili Cookoff

Sunday, October 19th, 5pm
Bring your best chili recipe to compete for bragging rights or bring a side dish to share. Categories include Best Chili, Most Unique Chili, and Best Side Dish.

Bucctoberfest Regatta

Saturday, October 25th
Regatta is $40 and includes 2 diner tickets. Invite your friends! Register now!

Extra Dinner Tickets (target 5:30pm): $15
Includes Bratwurst, Soft Pretzels, Red Cabbage, Potato Salad, Spaetzel, Various mustards and sauerkraut, Apple dessert
Request extra meal tickets be purchased by 23 October.

Event Page

High School/Middle School Sailing Team

Season begins Aug 26th and runs through October. Join anytime!

Sit on Top Kayaks and Stand up Paddle boards

SMSA has new boats available for member checkout.

Find out More

Prospective Member? Want to Join?

Please check out our Membership page for additional details.