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 relaxing late-summer cruise to the picturesque waterfront town of St. Michaels, one of the Chesapeake Bay's most beloved cruising destinations. This weekend offers a wonderful blend of scenic sailing, local food and drink, maritime history, and classic Chesapeake traditions. Whether you're looking to build cruising experience, spend time with fellow club members, or simply enjoy a weekend on the water, this trip has something for everyone.
After sailing across the Bay from Baltimore on Friday, we'll settle into the marina and enjoy an evening exploring St. Michaels. Participants will have the opportunity to visit St. Michaels Winery or Eastern Shore Brewing, both popular local favorites, before gathering for dinner at Foxy's Harbor Grille, a lively waterfront restaurant known for its fresh seafood, tropical atmosphere, and harbor views.
On Saturday, we'll enjoy one of the Chesapeake's most unique events—the Log Canoe Races, featuring historic racing sailboats and skilled crews. Participants will also have the option to visit the renowned Chesapeake Bay Maritime Museum, with its historic vessels and exhibits celebrating the Bay's maritime heritage, or spend the day exploring St. Michaels' charming shops, galleries, waterfront parks, and cafés.
Later that afternoon, we'll depart St. Michaels and cruise to a nearby protected river anchorage for a peaceful evening on the water. We'll gather for a casual potluck-style cookout under the stars before settling in for a relaxing night at anchor. On Sunday morning, we'll enjoy a leisurely breakfast aboard before weighing anchor and sailing back to Baltimore.
Tentative Itinerary
Friday: Sail to St. Michaels, visit St. Michaels Winery or Eastern Shore Brewing, and enjoy dinner at Foxy's Harbor Grille.
Saturday: Watch the Log Canoe Races with the option to visit the Chesapeake Bay Maritime Museum or explore the town before cruising to an anchorage destination for a cookout under the stars.
Sunday: Return sail to Baltimore.
Trip details, marina reservations, dinner reservations, and the final anchorage location will be shared closer to the departure date based on weather, river conditions, and slip availability.
Event Start Time
0730
Event End Time
1700 (+2 days)
Estimated Shared Costs
Slip fees: ~$125/night/boat -> $31/person for the trip; Anchorages available
Boat fuel fund: Suggested contribution $30/person
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.
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.
