The Downtown Sailing Center upcoming events

Georgetown and Fairlee Creek Weekend Sail (Friday, June 19, 2026)

Fri, 19 Jun 2026 11:00:00 GMT

Georgetown and Fairlee Creek 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.

Sail up to Georgetown, MD on the Sassafras River the first day to the Georgetown Yacht Harbor. Stay overnight on mooring buoys in the Marina. Go out to dinner at local restaurant on Friday evening. On Saturday morning we will do breakfast at local restaurant and then sail back down the Sassafras river and south down the bay to Fairlee Creek. Anchor upon arriving and swim that afternoon and also visit Oak Landing and Jellyfish Joel’s beach bar. Grill dinner aboard and watch sunset and relax. On Sunday morning have breakfast aboard and then sail back to DSC arriving mid to late afternoon.

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

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

*Skipper note: The channel in/out of Fairlee Creek is shallow and has a strong current. Recommend shallowest draft boats for this trip, and read up on the approach ahead of time.

Event Start Time

0700

Event End Time

1500 (+2 days)

Shared Costs

Friday’s sail to Georgetown is 40.9 nm, approx 8 hours sailing time, from DSC. Saturday’s sail from Georgetown to Fairlee Creek is 21 nm, approx 4 hours sailing time. Sunday’s sail from Fairlee Creek to DSC is 23.1 nm, approx 4.5 hours.

Slip Fee ($0.85/feet/night) for Georgetown Yacht Harbor

BOAT FUEL FUND: Suggested contribution $30/person

Shared cost for Saturday dinner on board: roughly $100/boat = about $25/person

Cruise Plan

Option1:

Sail from DSC to Georgetown Yacht Harbor (40.9 nm, 8 hours)
Moor in the harbor
Dinner and Breakfast in town
Sail from Georgetown Yacht Harbor to Fairlee Creek (21 nm, 4 hours)
Spend evening anchored, swim and BBQ dinner, Sunday breakfast BYO
Sail from Fairlee Creek to DSC (23.1 nm, 4 hours)

Option 2

Return: Sail back to DSC from Fairlee Creek anchorage. Arrive back at the DSC around 3 pm, depending upon departure time and wind.

Provisions

In the interest of everyone’s time to prep for this cruise, Albert will purchase the food (Sweet Dreams) for the cockpit cookout dinner. Then crew will split the cost of this meal and any add'l common supplies (via Cash, Cash App, Venmo, Zelle)

BYO:

(1) dinner ashore. Bring (3) lunches, (2) breakfasts, preferred beverage(s). Snacks: (with some to share) fruit , vegs , cheese , crackers , chips , pretzels , cookies , baked goods , etc.

Coffee☕️ prepared by the Ship’s Barista (JamesBr. or Alt. Vol.)

Ice & Water: Block ice, cube ice, and drinking water will be provided. Bring refillable insulated water bottle.

Suggested Gear(recommended):

Pack light - for the weather. Bring PFD, foulies, mid-layer, hat(s), sunscreen, insect repellant, swimsuit, towel, float toys, toiletries, medications(AN), change of clothes, change of deck shoes, light sleeping covers (pillow opt.), personal flashlight or headlamp, cell phone, USBa cord or battery pack, personal fan (battery-powered, USBa, or 12v auto plugs available).

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 10 PM on the day before the event.

Sail 250 Blue Angels Airshow and Grill Picnic Daysail (Sunday, June 28, 2026)

Sun, 28 Jun 2026 14:00:00 GMT

Sail 250 Blue Angels Airshow and Grill Picnic Daysail

Sail through the Baltimore Harbor to see the spectacular SAIL 250 ships from the water. Anchor at the Canton Waterfront to watch the Blue Angels Airshow from a unique vantage point on board. Enjoy a grilled picnic dinner and social time with your crewmates. Potluck: bring drinks and a side dish or dessert to share.

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

*Skipper Note: Stay up to date on Sail 250 restrictions and guidance and adjust plans as necessary.

Event Start Time

10:00

Event End Time

17:00

1.5 nm to Canton Waterfront Basin

20 minutes of sailing time to destination

0.6 gallons of fuel (round trip)

Shared Costs

BOAT FUEL FUND: Suggested contribution $5 per person

Shared cost for Grilling and supplies on board: roughly $50 per boat = $10 - $12 per person

Cruise Plan

Option 1:

Sail from DSC through Baltimore Harbor, observe Sail 250 boats
Anchor in Canton Waterfront Basin
Grill to prepare cookout lunch/ Potluck: Bring side dish or dessert and drinks to share
Watch Blue Angels Airshow between Noon and 4 p.m. (exact time of show TBD)

Return: Sail back to DSC; arrive at approximately 4:30 pm

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 10 PM on the day before the event.

Cruising Full Strawberry Moon Sail (Monday, June 29, 2026)

Mon, 29 Jun 2026 21:30:00 GMT

Cruising Full Strawberry 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.

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.

Fourth of July Weekend Cruise (Friday, July 03, 2026)

Fri, 03 Jul 2026 12:00:00 GMT

Fourth of July weekend Cruise

Enjoy a weekend of Fourth of July celebration! We will depart early on Friday July 3 for a sail across the Bay to Rock Hall, Maryland for dinner at the Waterman’s Crab House and Rock Hall’s July 3rd Fireworks over the Harbor. Then we’ll sail back to the western shore to Middle River for a grill-out while anchored, followed by a night of Fireworks for the 4th. On Sunday, we’ll sail home to the DSC where we plan on arriving on the docks in the mid to late afternoon.

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 8:00pm on the day before the event.

*Skipper note: Skippers should expect significant holiday weekend activity on the water and fireworks each night of the trip!

Event Start Time

0800

Event End Time

1700 (+2 days)

Shared Costs

Boat Fuel Fund: Suggested $30.00 per person

Slip Fees: $4.50 per foot ($144 - $171/boat based on vessel size). Equalized to $39/person/night based on two boats with total of 8 people (Friday night only)

Grill Cookout Dinner at anchor: $25/person (Saturday night)

Cruise Plan

Friday, July 3rd, Sail from DSC to Rock Hall Harbor, roughly 23.7 NM, approx 5.0-5.5 hours

Dock on Rock Hall Harbor at Haven Harbor South Resort Marina (fireworks take place over Rock Hall Harbor)
Free Shuttle bus to Town of Rock Hall, harbor & restaurant
Free Shuttle bus back to the Haven Harbor South Marina where we can watch fireworks from their private beach w/ bar and firepits
Saturday morning, breakfast aboard

Saturday July 4th, Sail from Rock Hall to Middle River, roughly 20.3 NM, approx. 4.5 - 5.0 hours

Anchor / Raft Up near Strawberry or Galloway Creek off of Middle River. Relax and swim, then grill out for dinner on the water.
Watch the barge and waterfront community shows at 39 18’25”N 76 24’26”W
Sunday morning, breakfast aboard.

Sunday July 5th, Sail from Middle River to DSC, roughly 22.5 NM, approx. 5.0 - 5.5 hours

Return to DSC between 1500-1700 Sunday July 5th

Provisions

Ice & Drinking Water: communal supply provided by skippers. Cold storage is available aboard.
BYO: Refillable water bottle, two (2) breakfasts, three (3) lunches, beverages, snacks (sharing is caring )
Cooking: limited to 2-burner propane boat stove (Akimbo), single -burner butane camp stoves (other cruisers) with small pots/pans are aboard for hot water, instant hot cereals, etc.
Coffee: We welcome a volunteer for ‘Cruise Barista’, to bring coffee, cream, creamer, sweetener to share, and to prepare on board each morning. Tea kettle, small coffee pots, and French press is aboard, or bring you own camp coffee-making gadgets.

4th of July Grill Out Dinner: Skipper Albert will pre-purchase all food items needed for the grill out and costs will be shared. Usually hamburgers & hot dogs with fixings and salads, but menu suggestions are welcome. Your favorite appetizer or dessert contributions are also welcome, but reply here to let Albert and others know in advance what you are bringing so we don’t overbuy or duplicate too much. Please let Albert know in advance of any dietary restrictions.

Suggested Gear

PFD, personal flashlight, hat, sunglasses, sunscreen, foul weather gear, windbreaker, change of clothes & shoes, bathing suit, toiletries, bath towel, light sleeping bag or sheet/blanket, Cell Phone w/USB charging cord. Optional: Pillow, USB,12v auto-plug, or battery-powered devices, personal fans.

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.