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Picnic Paddle to Cacaway Island Near Rock Hall - Advance Rentals Available





















This is a perfect way to finish the Pirates and Wenches Weekend at Rock Hall.  Our group did this paddle last August and had a terrific time discovering Cacaway Island.  We made a return visit on Memorial Day weekend, and found an even better beach for landing.  It's going to be an awesome day kayaking on Langford Creek, just a few miles from Rock Hall.

We love Chestertown and the Kent County area because it's a welcoming place with cool festivals, attractive restaurants, and many recreational opportunities.  Yet it's just one hour across the Bay Bridge from Annapolis.  The Chester River and its tributaries are generally friendly and safe, with varied scenery featuring beautiful homes, woodlands, and abundant birdlife along its shores.

Capt. John Smith never made it up the Chester River to Cacaway Island, but our group of intrepid explorers will make up for his oversight of this lovely area located just off the Chesapeake Bay.

The Paddle Up Langford Creek

We'll meet up at the new public boat ramp that's located at the end of Shipyard Lane, a side road off MD Rt. 20 about one mile before you reach Rock Hall.  There is plenty of free parking, porta-potties, and an excellent wide concrete ramp with docking area.  You can bring your own kayak and gear, or you can rent top quality equipment from Chesapeake Kayak Adventures.  Chuck will be there at the ramp with rental kayaks for those who've made an advance reservation.

Full information on Shipyard Landing can be found on the Chester River Water Trail site:

Our kayaking route from Shipyard Landing will go at a relaxed pace that takes us a little over three miles straight up Langford Creek toward the Chester River.  The destination will be Cacaway Island, a small uninhabited island in the middle of Langford Creek that's popular as an anchorage for sailboats.  Total roundtrip distance for this paddle will be 7-8 miles.

Anyone with basic kayak paddling skills should do fine on the protected waters of Langford Creek, but you should be prepared for the possibility of choppy water around Cacaway Island where it nears the larger Chester River.  Our group of recreational kayakers look out for each other, but we're not certified experts at rescuing novices.

All participants are responsible for their own personal safety!

Our paddle events have been very successful so far because we stick together as a group in case anyone needs assistance.  Let's keep it that way...

Be sure to bring a wide-brim hat, sunglasses, sunscreen, and plenty of cold water to stay hydrated.

The Picnic at Cacaway Island

Cacaway Island is a small privately-owned island that serves as an undisturbed habitat for birds and other wildlife.  People are not allowed to enter the island.  However, the island has nice beaches where folks from the sailboats often play in the surf area.  Our plan is to find a nice beach area where we can land the kayaks and have a picnic by the water without treading on Cacaway Island.  We will NOT go onto the island itself, so plan accordingly.































Bring something good to eat and drink in your kayak for our picnic. We never tell people what to bring, but they always exceed expectations to make each picnic a special and memorable experience. There's plenty to share, and nobody goes home hungry (or thirsty).

Great al fresco dining is one excellent benefit of having a creative and fun group of members in Second Half Rally.  ;-)

Following our picnic at Cacaway Island, we'll paddle back on the other side of Langford Creek to our starting point at Shipyard Landing.  We should be back at our cars by 4:00 pm or so.

Renting a Kayak From Chesapeake Kayak Adventures

If you don't have a kayak, you can easily rent one from Chuck McMillin at Chesapeake Kayak Adventures.  He rents high-quality Liquid Logic kayaks with a life vest and paddle at $50 for the whole day.  Some of Chuck's colorful kayaks are pictured below.

Chuck has many years of experience kayaking, teaching, and working with customers at L.L. Bean to make sure people enjoy their paddling experience. He now runs Chesapeake Kayak Adventures, a mobile kayak rental service and Meetup group.

Chuck provides boats and gear right at the ramp where you need them, as well as offering personal attention to get you launched safely.  He has ably handled kayak rentals for Second Half Rally members at several of our previous events.

The easiest way to arrange for a rental kayak is to email Chuck at [masked] so he will have your email address for contacting you.  Chuck will send PayPal invoices via email to those requesting rentals so they can conveniently pay online using their credit or debit card.

The charges are 100% refundable if the group cancels the event due to weather or if the participant cancels with more than 24 hours notice prior to the event.  If you have questions you can call Chuck at[masked]-3434.


If you don't, you will not have a boat because Chuck won't bring a kayak and gear for you.

Final Meetup Details

We'll need good kayaking weather for this event. A little rain won't stop us and can add to the adventure, but we will not paddle when excessive heat, high winds, lightning, or dangerous storms threaten our safety.

I'll post a notice here by 9:00 am on Sunday morning if we need to change plans or cancel due to the weather. Call Jake at[masked] with any questions.

I hope to see you there!



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  • Cindy

    Thanks, Jake! Great paddle. This one is on my list of top 10 favorites. Great people, perfect weather. Had a blast.

    August 14, 2013

  • Bobbe

    Yes, a perfect way to finish Pirate & Wenches Weekend with such a fun group of picnicking paddlers! Jake & Chuck you need to get a patent on your combo event fun! Thank you for keeping us all smiling with such enjoyable adventures!

    2 · August 12, 2013

  • Gail T

    Fun, fun, fun! Thank you Jake for the planning and Chuck for the kayaks! I enjoyed spending time with good people.

    August 12, 2013

  • Peggy

    Another fabulous time with the Jake's SHR !
    A great paddle coupled with great camaraderie of
    my SHR friends and some new paddlers. A great blend of GOOD people.
    Chuck's CKA group was a wonderful addition to the FUN.
    A special thank you to Chuck , Gloria, Bobbe, Gail and Rick for helping me learn some paddling skills, keeping my spirits up and watching my back.
    Know you are appreciated.
    Jake, what can I say ?
    Without your dedication and planning we all would not have had such a marvelous experience.

    1 · August 12, 2013

  • Jake

    Perfect weather, calm water, cool island, good paddle, and wonderful people! Chuck did a fine job as usual getting people on the water. Terrific picnic too. I had a great time. It was nice to meet some new folks, hang out with the Chucklings, and enjoy my favorite SHR members. We'll do it again!

    3 · August 12, 2013

  • Cindy

    Thank you Jake for a great day on the water, loved the picnic on the island. Sun, swim, sand, surf, sensational! Thank you Chuck for all your help and bringing rentals. It was extra fun trying different kayaks and paddling with your group.

    August 12, 2013

  • Denise Parisi *.

    Thanks for a fun day, Jake. This topped off a playful weekend. Lots of laughs. Company and food was great.

    August 12, 2013

  • Gloria

    Fantastic day for a paddle! I love it when Chuck outfits the paddle cuz then we get to hang with the CKA crew! And the food was phenomenal! Jake... your Thai chicken lettuce wraps and Gail's peach cobbler [gasp] AMAZING! Thanks Jake and Chuck for making this a great day in and on the water!

    August 12, 2013

  • Chuck

    It was an excellent day Jake. Thanks

    August 11, 2013

  • Yoshiko

    Thank you for the fun time and good food, Jake, you are the best cook!

    August 11, 2013

  • Rick O.

    Excellent gathering. Wonderful group with conversation, tasty food to share and a beautiful environment.

    August 11, 2013

  • Kimmie

    Back killing me after weekend. Sorry!

    August 11, 2013

  • Donna M

    Sorry for this last minute notice but I can't make it tomorrow. I can't find Chuck's phone number. Will someone please tell him for me?

    August 10, 2013

  • Chuck

    Hey Everyone - Are you psyched about this weekends Pirates and Wenches Festival yet? I just wanted to confirm that I will be bringing rental boats for Peggy, Gail, Donna, Randi (x2), Sonja (x2) and Cindy. I will be bringing a total of 12 rentals so there is still time to reserve one of the 4 that are left. I'm leaving for rock hall shortly and will have limited Internet access so email me or post here if you still want a boat.

    August 9, 2013

    • Sonja

      I will need just one kayak.

      August 9, 2013

  • Del

    Hey Rick I am close, can carpool.

    August 7, 2013

  • A former member
    A former member

    Out of town company coming this weekend. See you soon!

    August 7, 2013

  • Rick O.

    Any interest in ride sharing? I can carry a second kayak. Any kayak renters need a ride? I'm leaving from Severna Park area.

    August 6, 2013

  • Rick O.

    Have kayak, will paddle!

    August 6, 2013

  • Becky

    bringing a guest

    August 4, 2013

  • Sonja

    Looking forward to a great paddle!

    July 8, 2013

  • Gloria


    June 21, 2013

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