The Downtown Sailing Center upcoming events

Cruising First Thursday Sail (Thursday, July 09, 2026)

Thu, 09 Jul 2026 21:30:00 GMT

Cruising First Thursday Sail

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.

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

Event Start Time

1730

Event End Time

2130

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!

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 11 AM on the day of the event.

St. Michael's Log Canoe Racing Weekend Sail (Friday, July 24, 2026)

Fri, 24 Jul 2026 11:00:00 GMT

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.

Bodkin Creek Daysail and Swim (Sunday, July 26, 2026)

Sun, 26 Jul 2026 11:00:00 GMT

Bodkin Creek Daysail and Swim

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.

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 10:00pm 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'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 info@downtownsailing.org. Weather cancellations will be announced by 10 PM on the day before the event.

Cruising Full Buck Moon Sail (Wednesday, July 29, 2026)

Wed, 29 Jul 2026 21:30:00 GMT

Cruising Full Buck Moon Sail

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.

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 11 AM on the day of the event.

Event Start Time

1730

Event End Time

2130

Shared Costs

No slip or dockage fees expected. Please consider a $5 contribution to the fuel fund!

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

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!

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 11 AM on the day of the event.

Cruising First Thursday Sail (Thursday, August 06, 2026)

Thu, 06 Aug 2026 21:30:00 GMT

Cruising First Thursday 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.

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

Event Start Time

1730

Event End Time

2130

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!

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 11 AM on the day of the event.

Bodkin Creek Daysail and Swim (Sunday, August 09, 2026)

Sun, 09 Aug 2026 11:00:00 GMT

Bodkin Creek Daysail and Swim

Prepare to start the day early so we can take advantage of more time to swim!

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

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'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 info@downtownsailing.org. Weather cancellations will be announced by 10 PM on the day before the event.

Whitehall Bay and Cantler's Overnight (Saturday, August 15, 2026)

Sat, 15 Aug 2026 12:00:00 GMT

Whitehall Bay and Cantler's Overnight

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.

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.

Cruising Full Sturgeon Moon Sail (Friday, August 28, 2026)

Fri, 28 Aug 2026 21:30:00 GMT

Cruising Full Sturgeon Moon Sail

Join us for a casual evening sail to catch the full moon out on the water.

Learning Objectives: practice night navigation, recognizing other vessels lights and using lighted markers, docking at night.

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 11 AM on the day of the event.

Event Start Time

1730

Event End Time

2130

Shared Costs

No slip or dockage fees expected. Please consider a $5 contribution to the fuel fund!

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

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!

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 11 AM on the day of the event.

Bodkin Creek Daysail and Swim (Saturday, August 29, 2026)

Sat, 29 Aug 2026 11:00:00 GMT

Bodkin Creek Daysail and Swim

Prepare to start the day early so we can take advantage of more time to swim!

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

Event Start Time 0700

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'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 info@downtownsailing.org. Weather cancellations will be announced by 10 PM on the day before the event.

Cruising First Thursday Sail (Thursday, September 03, 2026)

Thu, 03 Sep 2026 21:30:00 GMT

Cruising First Thursday 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.

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

Event Start Time

1730

Event End Time

2130

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!

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 11 AM on the day of the event.

Labor Day Weekend Swim and Crab Feast Daysail (Sunday, September 06, 2026)

Sun, 06 Sep 2026 12:00:00 GMT

Labor Day Weekend Swim and Crab Feast Daysail

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.

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

8:00

Event End Time

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)

Shared Costs

BOAT FUEL FUND: Suggested contribution $5 per person

Individual Costs

Meal items at Mike’s Crabhouse North

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 info@downtownsailing.org. Weather cancellations will be announced by 10 PM on the day before the event.

September St. Michael's Log Canoe Racing Weekend Sail (Friday, September 11, 2026)

Fri, 11 Sep 2026 11:00:00 GMT

St. Michael's Log Canoe Racing Weekend Sail

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

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.