CBMM will offer a variety of opportunities to sail aboard Rosie Parks this fall. (Photo by Sharon Thorpe)

Aug. 27, 2026 | #MyChesapeakeStory

This fall, the Chesapeake Bay Maritime Museum is excited to get 1955 skipjack Rosie Parks out on the water for sails on the Miles River and beyond.

We’re offering three distinct experiences with weekly Evening Sails, Skipjack Sail Training in conjunction with annual skipjack races around the Bay, and Fall Festival Sails.

After going on the rails in our working Shipyard for its annual maintenance under the care of our shipwrights, shipwright apprentices, and volunteers, Rosie Parks is looking great and ready for a busy few months ahead.

Each experience is limited to six guests—Don’t wait to reserve your spot!

Join our skipjack racing crew!

Are you ready to race? Join our crew of Shipyard staff and volunteers in September aboard Rosie Parks as part of the annual races in Deal Island, Annapolis, and Cambridge.

We have opportunities to join us on Rosie Parks for race day as well as sails to and from the race locations. Along the way, you’ll learn helmsmanship, sail handling, rules of the road, basic navigation using physical and digital charts, sail evolutions and theory, engine operations, vessel anatomy and terminology, skipjack historical developments, and history of the vessel and its builder.

The cost is $120 for CBMM members and $150 for non-members. (Please note that transit sails start and end at CBMM and include a van ride to/from the race location.)

Don’t miss your chance to be part of this unique Bay tradition aboard a piece of Chesapeake history!

Deal Island (67th Annual Deal Island Skipjack Race & Festival)

• St. Michaels to Deal Island, Friday, Sept. 4
• Deal Island Race Day, Monday, Sept. 7
• Deal Island to St. Michaels, Tuesday, Sept. 8

Annapolis (Skipjack Heritage Days)

• St. Michaels to Annapolis, Friday, Sept. 11
• Annapolis Race Day, Sunday, Sept. 13
• Annapolis to St. Michaels, Monday, Sept. 14

Cambridge (Choptank Heritage Skipjack Race)

• St. Michaels to Cambridge, Thursday, Sept. 24
• Cambridge to St. Michaels, Monday, Sept. 28

The perfect evening starts on the water!

In September and October, we’re thrilled to offer Evening Skipjack Sails aboard Rosie Parks every Wednesday from 5-7pm.

You’ll cruise past waterfront homes, working shorelines, and marshes along the Miles River that once supported a thriving oyster industry, and even glimpse the weekly sailing races in St. Michaels. Along the way, the crew is happy to share how skipjacks like Rosie Parks harvest Chesapeake oysters and became the nation’s last commercial sailing fleet.

Join us Sept. 2, Sept. 9, Sept. 16, Sept. 23, Sept. 30, Oct. 7, Oct. 14, Oct. 21, and Oct. 28.

The cost is $64 per passenger for CBMM members and $80 for non-members.

Level up your festival fun!

We’re excited to add to the fall festival fun ahead with Rosie Parks sails at OysterFest and the Holiday Edition of the Eastern Shore Sea Glass & Coastal Arts Festival. These 90-minute sails include your festival admission. The cost is $35 for CBMM members and $45 for non-members.

OysterFest Skipjack Sails: What better way to celebrate the Bay’s favorite bivalve than a skipjack sail? Join us Saturday, Nov. 7, for oysters prepared a variety of ways and more fun for the whole family, plus a memorable on-the-water experience.  We have limited spots available on the noon sail after selling out the 10am option.

Holiday Sea Glass Festival Skipjack Sails: While you’re getting a jump on your holiday shopping with dozens of unique vendors during a festive celebration, you’re invited to get out on the water aboard Rosie Parks. We still have tickets available for sails at 10am and noon.

Looking for more on-the-water experiences? Click here learn more about Patriot Cruises, Historic Workboat Experience cruises, Old Point Miles River Cruises, Crabbing the Miles River, and guided paddles available this fall.