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The Sailing Club, Inc.

Tilghman Island Day

October is a fantastic time of year to sail the Chesapeake. This four day trip takes advantage of the opportunity before the sailing season ends for 2017. The trip revolves around Saturday's events on Tilghman Island, Maryland - eponymously called Tilghman Island Day. This is a local seafood fest that celebrates the crab and oyster industry heritage of the area. Bring your camera and your party attitude!

We will be chartering from Haven Charters out of Rock Hall, MD and will be working with Haven Charters so that Skippers and First Mates should be able to do boat checkouts on Thursday afternoon. After boats are checked out, crew may load provisions and personal items on board. All provisions should be on board Thursday night as there will not be time to pick up last minute items on Friday morning. After the boats are ship-shape, crews will meet at a local restaurant for grub and grog.

Friday is a day of sailing! Embrace the day! We want to get an 8:00 a.m. start to allow time for the 32 mile sail to Knapps Narrows Marina at Tilghman Island. The skippers meeting will be Thursday evening to facilitate this. Crews may choose to eat breakfast while underway or have a quick breakfast before casting off. Lunch will definitely be while underway. Later in the day, skippers and crews will expertly navigate the narrow channel that brings us to Knapps Narrows Marina. If you arrive early, be sure to stay near your boat to observe the other boats pulling in and to be ready to lend a hand with docking. The current in this channel can be strong and present a challenge. Not to worry, we have local knowledge of the area's currents and shoals. We will be at the slips for Friday night through Sunday morning, giving plenty of time to pick up any provisions that might have been forgotten on Thursday evening. We will plan on eating at a local restaurant on Friday night.

Saturday is the day to enjoy the land after Friday's seafaring adventure. The Tilghman Island Day festivities officially begin at 10:00 a.m. and end at 4:30 p.m. giving plenty of time to discover the culture of the crabbing and oystering families of years past. The events start off with a rowboat race, one of the few opportunities for visitors to show off their skills. This is followed by a "jigger toss." A jigger is a special anchor that was tossed off the side of the sail-driven skipjacks to maneuver about the oyster beds. One can quickly realize that long tosses of the jigger provided a commercial advantage in how quickly a boat and crew could harvest the oysters in an area. This helps explain the intense competition between the locals in this event. Later, the local fishing boats partake in docking contests and workboat races. Now would be a good time to think about the powerful appetite that's been building and find one of the churches and firehouses selling food as part of this firehouse fundraising event. The menus are varied but the theme is seafood so you will find crab cakes, soft-shell crab, oysters, fried clams and more traditional luncheon fare such as BBQ chicken, hotdogs, burgers and fries. Don't forget to try the oyster shooters and wash this down with some beers to prepare for the music at Kronsberg Park where the music is made to dance to. Then back to serious business. The crab-picking and oyster shucking contests capture the full attention of the crowd. Each boat is on their own for dinner on Saturday evening, and there will be lots of time for socializing at the marina.

After a leisurely breakfast on Sunday, we set sail back north for a yet to be determined secluded cove. Weather conditions will determine our choice of western or eastern shore location for our raft up. Bring your hors d'oeuvres to share with the other boats for an evening of socializing and appetizers.

Monday morning we'll head back to Rock Hall, enjoying the sail and lunch along the way. We will want to arrive by late afternoon to return the boats, unload and, hopefully, meet on shore to say goodbye and car pool.

The cost of the trip is $475.00 per person (Skippers and Trip Leader- $254.00). The trip price includes charter fees, and two nights' slip fees in Knapps Narrows. Provisioning, 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 Joel Mack at the address below. Reservations will be processed beginning April 8, 2017 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 $375.00 will be due September 5, 2017. The Club's standard thirty-day cancellation policy applies for this event.

A pre-trip meeting will be held approximately two 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

Joel Mack                      
150 Kings Hwy
Middletown, NJ 07748                      
Steve Krakauer                      
11 Clark Court
Basking Ridge, NJ 07920



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Current Trips

Schedule of our trips

OWT Trip

Rock Hall, MD
May 20-21

June Trip

June 24-26

July Trip

Day Sail
Barnegat Bay
July 9

Sept. Trip

Baltimore Inner Harbor
Sept. 15-18

Jan/Feb 2018

Winter Get-Away
Jan 27-Feb 6 2018