Cruising skipper registration slots are open immediately and we encourage skippers to sign up as soon as they know they can commit to an event. Cruising crew slots open 6 weeks out from the event start date.

General Overview

Experience one of the Chesapeake Bay's favorite fall traditions with an overnight cruise to the charming waterfront town of Rock Hall for its annual Fall Fest. We'll sail across the Bay to Maryland's Eastern Shore, spend the night in one of Rock Hall's welcoming marinas, and enjoy a day exploring a festival that celebrates the town's rich watermen's heritage with fresh oysters, local seafood, live music, and artisan vendors.

For additional information about Fall Fest please refer to https://rockhallfallfest.org/program/ or https://www.facebook.com/rockhallfallfest/. Fall Fest is from 10am - 4pm, so with a four hour cruise to reach Rock Hall, please note we plan to leave the DSC docks early and promptly on Saturday morning.

Skipper(s) will contact participants via Circle to communicate the actual dock-call time and cruising logistics.

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

Weather cancellations will be announced by 10 PM on the day before the event.

Event Start Time

0700

Event End Time

1500 (+1)

Estimated Shared Costs

Slip fees: ~$140/boat -> ~$35/person

Boat fuel fund: Suggested contribution $10/person

Optional - individual paid dinners from food vendors at Fall Fest

Learning Objectives: Navigation (electronic and/or paper charts), checking tides and appropriately timing passage through shallow areas, docking and departing a busy marina

Crew sign-ups may be admitted from the waitlist if additional skippers register for the event and we’re able to add another boat.

Weather cancellations will be announced by 10 PM on the day before the event.

Waivers Required

If you're new to the DSC or haven’t signed the DSC liability waiver yet, please complete it online. Skippers must also sign the SKIPPER WAIVER.

Have Questions?

If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 8 PM on the day before the event.