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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; the Tilghman Island Day festival, featuring the bounty of the bay: crabs, oysters, and barbecued chicken; as well as skipjacks, the work boats of the watermen of the past; and gorgeous harbor views. We will be in slips at Knapp’s Narrows Marina this year, making getting to and from the festival an easy walk over the bridge to Tilghman Island at your own pace. Or take advantage of the festival provided school buses that depart from the marina's parking lot.

On Thursday, October 14th, we will make our way to Haven Sailing Charters, Rock Hall, MD. Two 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. For friends and family of the club that don’t want to be on a sailboat but would like to attend the festival and enjoy the festival with us, check out rooms at: Knapp's Narrows Marina & Inn

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 two 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 is the main event, “the” Eastern Shore event - Tilghman Island Day. The schedule of events from 2019 is below. When the 2021 schedule is posted it will be very similar and although many of us focus on the food, the celebration is to honor the people, the heritage, natural beauty and the “old way of life before it disappears.” Bring your camera and your party attitude! Participation by visitors is encouraged and you may want to try your hand at the jigger toss (a small anchor) or rowboat race!

It's a short walk between the popular docking contest and the jigger toss. Both contests are crowd favorites, providing lots of excitement, splashing and encouraging shouts. Right about this point in time your stomach reminds you it's lunch time, and your brain clicks in with the knowledge that there’s a whole lot of freshly prepared food waiting! Some favor the crab soup at the local church, others head back to the firehouse for steamed crabs, crab cakes, raw and steamed oysters, oyster stew and fried clams. There are also hot dogs, burgers, fries, barbequed chicken, cookies, cakes and ice cream! Don't forget to try the oyster shooters and a cold beverage of your choice to prepare for the band starting up at Kronsberg Park where the music is made for dancing!

Then it’s back to some serious business. The crab-picking and oyster shucking contests capture the full attention of the crowd at Kronesberg Park starting about 3:30 pm. And this hint from past attendees - if you get a spot up front and ask nicely, the oyster shuckers and the crab pickers will hand you the result of their labors! Each boat’s crew is on their own for dinner on Saturday evening, and there will be lots of time for socializing at the marina or perhaps an evening bike ride before sunset.

Tilghman Island Day Schedule

10:00 AM to 5 PM

All exhibits open at 10:00 AM

  • Rowboat Races

  • Anchor Toss

  • Boat Docking Contest

  • Workboat Races

  • Crab-picking contest

  • Oyster shucking contest

  • Seafood - oysters (raw and steamed), oyster fritters, oyster stew

  • Steamed crabs, crab cakes, soft-shell crabs

  • Crab soup, hamburgers, hot dogs, barbeque chicken, fries, and more

  • Live Music


There will be plenty of ice-cold beer, wine, sodas and water; and nautical artisans and craft vendors. Admission is a donation of $5 per person to the Tilghman Island Fire Department..


On Sunday, we’ll depart north to Rock Hall.  Since we will be retaining the boats for a second cruise, there should be plenty of time to enjoy the Chesapeake on the way.


We’ve reserved two Catalina 425s from Haven Charters – Cathy Sea and Dilly Dilly. 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, 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