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Whitehall Bay and Cantler's Overnight

  • Saturday, August 15, 2026
  • 8:00 AM
  • Sunday, August 16, 2026
  • 5:00 PM
  • 1425 Key Highway, Baltimore, MD 21230
  • 7

Registration

Register

Whitehall Bay and Cantler's Overnight

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

Nestled between the Bay Bridge and Annapolis, Whitehall Bay is one of the Chesapeake Bay's favorite protected anchorages. Join us for a relaxing overnight cruise amidst wooded shorelines and quiet coves. We will practice anchoring, enjoy a sunset on the water, and share a dinner together at Cantler’s Riverside Inn on Mill Creek.

Learning Objectives: Navigate a particularly winding and shallow channel, anchoring, potentially rafting up with appropriate offset and use of lines, using either dinghy or dock and dine options at Cantler's pier.  

Event Start Time

0900

Event End Time

1500 (+1)

Estimated Shared Costs

Slip fees: Not anticipated - overnight at anchorage

Boat fuel fund: Suggested contribution $10/person

Dinner paid for individually at Cantler’s Riverside Inn

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 10:00 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.