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The Sailing Club, Inc.

The Winds Of October

The Winds of October October on the Chesapeake is a magical time of adventure and exploration. The combination of lingering warm weather and exciting autumn events make it a perfect time to plan a weekend getaway on the water.

This autumn trip combines some of the best Chesapeake Bay sailing conditions with a visit to historic Annapolis, Maryland and - best of all for some sailors - the Annapolis Sailboat Show. We're chartering some of our favorite boats from Haven Charters in Rock Hall, which allows time for some good sailing before reaching port, without the risk of running out of time.

Thursday, October 4
Arrive in Rock Hall and settle aboard the boats. Dinner at one of Rock Hall's seafood restaurants.

Friday, October 5
Depart Rock Hall and sail to Annapolis, which is only about an eighteen mile sail from Rock Hall, so we don't have to go directly there. If conditions are right, a sail on down the Bay to Thomas Point light or further may be in order. However, sailing directly to Annapolis will get us there in time to attend the Sailboat Show late Friday afternoon. We will have slips reserved at a marina within walking distance of town that is served by the Annapolis water taxi.

Saturday, October 6
Attend the United States Sailboat Show in Annapolis. Since not all of the crew might be interested in attending the Show, Annapolis offers many other activities such as touring the Naval Academy and historic Annapolis, and the Maryland State House. Quiet Waters Park and a number of historic churches are within walking distance of the marina. There are also many restaurants within walking distance.

If one of the skippers and a first mate are interested, one of the boats could go out for a sail for some or all of the day instead of attending the show.

Sunday, October 7
A leisurely return sail to Rock Hall is planned. Again, since it's not a long distance, we can enjoy some classic fall Chesapeake sailing. And since the next day, Monday, is Columbus Day, we may find lighter traffic for the drive home.

The cost of this trip is $420.00 per person (Skippers and Trip Leader - $227.00). The price includes charter fees and slip fees for two nights. Food, fuel, pump-out, 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 Mia McCroskey at the address below. Reservations will be processed beginning April 7, 2018 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 $320.00 will be due on August 21, 2018. The Club's standard thirty-day cancellation policy applies for this event.

A pre-trip meeting will be held a few weeks before the trip, at a time and place to be announced. All participants 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

Eleanor Popolizio                     
43 Mt. Pleasant Pkwy.
Livingston, NJ 07039
Mia McCroskey                      
19 Manor House Drive, K12
Dobbs Ferry, NY 10522



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Havre De Grace, MD
June 2-3


Magothy River
June 23-25

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Barnegat Bay
July 8

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August 5-12

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Camden, ME
September 9-14

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February 2019