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Cruising Calendar

Upcoming events

    • Sunday, September 27, 2026
    • 7:00 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 0
    Join waitlist

    Cruising Full Corn 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 (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.

    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

    1730-1900

    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.


    • Saturday, October 10, 2026
    • 7:00 AM
    • Sunday, October 11, 2026
    • 3:00 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 2
    Register

    Rock Hall Fall Fest 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

    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.

    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

    1500 (+1)

    Estimated Shared Costs

    Slip fees: ~$140/boat -> ~$35/person

    Boat fuel fund: Suggested contribution $10/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

    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.


    • Monday, October 26, 2026
    • 6:00 PM - 9:30 PM
    • 1425 Key Highway, Baltimore, MD 21230
    • 2
    Register

    Cruising Full Hunter's 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 (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.

    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

    1730-1800

    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.