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The Sailing Club, Inc.




October is a fantastic time of year to sail the Chesapeake. This trip takes advantage of the best the Eastern Shore has to offer all packed into three days! There will be great sailing to Knapps Narrows and Tilghman Island. We will be in slips at Knapp’s Narrows Marina this year, making getting to and from the island an easy walk over the bridge.

On Thursday, October 14th, we will make our way to Haven Sailing Charters, Rock Hall, MD. Three sleek and graceful sailboats will be awaiting us. Trip Leaders will coordinate with Haven to try to have boat checks on Thursday afternoon. Once boats are checked out and your skipper has given the okay, crews may load personal items and provisions on board. Skippers will coordinate for a group dinner at a Rock Hall restaurant for dinner about 6:00 p.m. and we can get to know one another and catch up with old friends. The skippers will meet either Thursday evening or 8:00 a.m. Friday.

Friday, October 15th, we are planning a reasonably early departure at 9:00 a.m. to allow time for the 24 NM sail. We have three slips reserved at Knapp’s Narrows Marina. It has modern docks and facilities: showers, rest rooms, laundry, picnic benches and barbeque grills and yes, WiFi. Kayaks and paddle boards are available for rental at the marina office. Perhaps a sunset paddle?

Saturday, October 16th - Although the festival has been cancelled, there are many other interesting activities in the area: Quite possibly, one or more boats will be going out for a day sail on the Bay or the Choptank River, returning to the marina in the late afternoon. Other area activities may be found by visiting and

Regardless of your daytime activities, a group dinner has been planned at Marker 5 Restaurant, just a short walk over the bridge Please not that the group dinner is not included in the trip price).

We’ve reserved three Catalina 425s from Haven Charters – Cathy Sea, Dilly Dilly and Akula. Each has three cabins and two heads.

The cost of this trip is $380.00 per person (Skippers and Trip Leader- $207.00). The price includes charter fees and two nights' slip fees at Knapps Narrows Marina.. Provisioning, fuel, pump-out, dinner at Markers, and other incidentals are additional and will be handled by each boat's crew. A $100.00 deposit and Release of Liability and Zero Tolerance Form must accompany your Reservation Form.

Please make your check payable to The Sailing Club, Inc. and mail it, along with your completed reservation and release forms, to Gary Brubaker at the address below. Reservations will be processed beginning April 3, 2021 with a random draw of those received by that date. All reservations received after that date are on a first-come, first served basis. The balance of $280.00 will be due August 31, 2021. The Club's standard thirty-day cancellation policy applies for this event.

BONUS: Should you sign up for this trip and the Chesapeake II trip immediately following, you will receive a $50 discount on each trip, a total savings of $100.00 (skippers and trip leaders excluded).

A pre-trip meeting will be held approximately two weeks before the trip, at a time and place to be announced. All crewmembers should make every effort to attend in order to meet your crewmates, plan your meals, and make travel plans.

Please note that sailing conditions are dynamic, that your safety, and that of your crewmates, depends on your good physical health and agility.


Trip Leader     

Assistant Trip Leader

Gary Brubaker                    
554 Marietta Ave.
Swarthmore, PA19081                      
Mary Ann Gordon
2714 Packer Court
Bridgewater, NJ 08807



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Current Trips

Schedule of our trips


Rock Hall, MD
June 26-27, 2021

Mallorca, Spain

The Balaeric Islands
September 11-18, 2021

Chesapeake II

Rock Hall, MD
Herrington Harbor
October 18-21, 2021

Winter Getaway

Someplace Special