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St. Michael's Log Canoe Racing Weekend Sail

  • Friday, July 24, 2026
  • 7:00 AM
  • Sunday, July 26, 2026
  • 5:00 PM
  • 1425 Key Highway, Baltimore, MD 21230
  • 6

Registration


Register

St. Michael's Log Canoe Racing Weekend Sail

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

Join us for a weekend cruise to the historic waterfront town of St. Michaels to experience one of the Chesapeake Bay's most distinctive sailing traditions: Chesapeake Bay log canoe racing. These remarkable wooden boats trace their origins to 19th-century oystering workboats and are now raced by crews who balance towering sail plans by climbing onto long springboards extending over the water. Today, many of the competing boats are over a century old and continue to race throughout the summer regatta season.

We'll sail across the Bay to St. Michaels and spend the weekend enjoying the town's maritime character, waterfront restaurants, and local attractions before positioning ourselves on the Miles River to watch the racing fleet in action.

Learning Objectives: Navigation (electronic and/or paper charts) through Kent Narrows and/or Bloody Point, checking tides and appropriately timing passage through shallow areas, anchoring in a crowded zone, docking and departing a busy marina, rafting up with appropriate offset and use of lines.

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

1700 (+2 days)

Estimated Shared Costs

Slip fees: ~$125/night/boat -> $65/person for the trip; Anchorages available

Boat fuel fund: Suggested contribution $30/person

Shared cost for cookout meals on board: roughly $120/boat = about $30/person

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.