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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
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.
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.
Come aboard to a popular DSC location for a smooth daysail on the Bay followed by lunch and a swim while anchored in Bodkin Creek. Expect about a 28 nautical mile round trip for a full day on the water.
Prepare to start the day early so we can take advantage of more time to swim!
Learning Objectives: navigate a typically narrow chesapeake bay channel through shoaling to a popular recreational swim area, anchor, coordinate a meal aboard with other crew, potentially use a propane or charcoal grill at anchor.
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 10:00pm on the day before the event.
Event Start Time0700
Event End Time 1700
Shared Costs
$5 recommended fuel fund contribution. Shared cook-out costs are possible and will be discussed among skipper(s) and crew before departure.
Waivers Required
If you have any questions, please contact the DSC office at info@downtownsailing.org. Weather cancellations will be announced by 10 PM on the day before the event.
Join us for a casual evening sail to catch the full moon out on the water.
The plan is to head out around sunset, sail through dusk, and be on the water as the moon rises. Depending on conditions, we’ll keep things flexible—maybe a relaxed cruise, maybe a bit more hands-on sailing if people are interested. Everyone is welcome to participate as much or as little as they’d like, whether that’s helping out with the boat or just settling in and taking it all in.
Learning Objectives: practice night navigation, using your own nav lights and recognizing other vessels lights and using lighted markers, docking at night.
Weather cancellations will be announced by 11 AM on the day of the event.
1730
2130
No slip or dockage fees expected. Please consider a $5 contribution to the fuel fund!
If any availability remains a week prior to the event, dayfleet skippers and crew are able and encouraged to register and check out all the Cruising program has to offer at the DSC!
If you have any questions, please contact the DSC office at 410.727.0722 or info@downtownsailing.org. Weather cancellations will be announced by 11 AM on the day of the event.
Join us for an evening sail as we meander to the Canton Waterfront park to take-in WTMD’s First Thursday concert! We may or may not dock in Canton, so plan to bring a snack to hold you over on this evening sail.
Learning objectives: participate in coordinating an evening cruise with an experienced skipper, handling lines while docking in a busy marina, or anchoring near a large public event.
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.
0900
1500 (+1)
Slip fees: Not anticipated - overnight at anchorage
Boat fuel fund: Suggested contribution $10/person
Dinner paid for individually at Cantler’s Riverside Inn
Learning Objectives: practice night navigation, recognizing other vessels lights and using lighted markers, docking at night.
Event Start Time 0700
Sail to Bodkin Creek to enjoy the best of the waning days of summer with friends on the water! Anchor, raft up and swim. On the return trip, stop at Mike’s Crabhouse North in Pasadena to dock and dine for a delicious seafood dinner by the water (non-seafood menu items are available too.) Bring snacks and drinks to share on the boat.
Learning Objectives: Anchoring, rafting up with another boat using appropriate offsets and use of lines, navigating a narrow channel into a popular swim area.
8:00
17:00
11.3 nm from the DSC to Bodkin Creek
2.5 hours sailing time to Bodkin Creek (arrive around 11 a.m.)
3.2 nm from Bodkin Creek to Mike’s North Restaurant
40 minute sailing time from Bodkin Creek to Mike’s Crabhouse in White Rocks Marina (leave Bodkin at approximately 1:00 pm; arrive at Mike’s approximately 1:40 pm)
Lunch at the restaurant (1:45 - 3:15 pm)
8.7 nm from Mike’s to the Downtown Sailing Center
1 hour 45 minutes sailing time (leave at approximately 3:15 pm; arrive at approximately 5 p.m.)
4.5 gallons of fuel (round trip)
BOAT FUEL FUND: Suggested contribution $5 per person
Individual Costs
Meal items at Mike’s Crabhouse North
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.
0730
Slip fees: ~$125/night/boat -> $31/person for the trip; Anchorages available
The plan is to head out around sunset (please check circle for a message from the skippers about a specific time to meet!), sail through dusk, and be on the water as the moon rises. Depending on conditions, we’ll keep things flexible—maybe a relaxed cruise, maybe a bit more hands-on sailing if people are interested. Everyone is welcome to participate as much or as little as they’d like, whether that’s helping out with the boat or just settling in and taking it all in.
1730-1900
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.
Slip fees: ~$140/boat -> ~$35/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
1730-1800
The Downtown Sailing Center
1425 Key Highway, Suite 110, Baltimore, MD 21230(410) 727-0722 • info@downtownsailing.org
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