Chesapeake Sport Pilot

10/11/2026

Congratulations to William Borreson Coward for completing his first solo yesterday in the Tecnam P92.

He is studying under Lance Tuscany and Chris Criswell

10/09/2026

Please join Chesapeake Sport Pilot in congratulating Eraldo Cardoso we’re earning his pilot certificate today. Eraldo studied under Gary Capkovic and has the following words of wisdom to share the student pilots everywhere:

To all student pilots:

You chose one of the hardest paths in the world. The path that demands everything from you, your focus, your patience, your discipline, your mind.

But that’s what makes it worth it, because not everyone can handle this. Not everyone can spend nights studying while everyone else sleeps, not everyone can take failure, rejection and fear.

And still walk in the cockpit the next day ready to win. But you can, that’s what separates you from the rest, every flight, every late night, every time you pick yourself up after a bad day.

It’s building something inside you that no one can teach resilience, unshakable belief, the mind set of a pilot. So when it gets hard remember this, you are not just learning to fly planes. You are learning to master yourself.

Eraldo (Junior) Cardoso

10/08/2026

We’re starting to gear up for our Holly Run to Tangier Island at the beginning of December, and looking at these pictures reminds us just how much this trip means to us.

It’s about seeing familiar faces, taking time to sit and visit, lending a helping hand, and sharing a little Christmas joy. The moments that might seem small like a smile, a conversation, a warm welcome are the ones that stay with us long after we fly home.

As we get ready for this year’s visit, we’d love for you to be part of it. Please visit our website to learn more about the Holly Run and find out how to donate:

https://hollyrun.my.canva.site/home

Whether you’re able to donate or simply share this post, thank you for helping us keep this special connection with Tangier Island going. This trip takes a lot of helping hands and caring hearts, and we’re grateful for every one of you.

We’re looking forward to seeing you, Tangier! 🎄❤️

10/05/2026

It’s time for our annual Lost and Found purge at Chesapeake Sport Pilot. If any of these items belong to you, please plan to pick them up this coming week or this coming weekend or they will be given to charity.

09/30/2026

09/23/2026

Join us in congratulating Mitchell Breeden for completing his Sport Pilots License this past weekend.

He studied under Lance Tuscany. Congratulations to you both!

09/19/2026

Chesapeake Sport Pilot would like to thank everyone who volunteered for or came out to our Fall open house. Our volunteers flew 54 neighborhood kids today and had a blast with your families. We look forward to seeing you again this time next year. 

09/19/2026

Congratulations to Nicholas Russell on getting his Instrument Rating yesterday. This time, he studied under Vince Massimini. We can't wait to see what he does next!

09/17/2026

🚨 FREE KIDS’ FLIGHT REGISTRATION IS NOW CLOSED! 🚨

WOW! We have an amazing number of young aviators registered for our FREE flights at Open House!

A QUICK BUT IMPORTANT NOTE FOR REGISTERED FAMILIES:
We ask that you plan to arrive anytime between 9:00 AM and 12:00 PM and check in when you arrive. Please be prepared for a wait, as flights will be handled in the order of check-in.

NOT REGISTERED? PLEASE DO NOT COME EXPECTING A FLIGHT. Registration is officially CLOSED, and we cannot accommodate walk-ins.

Thank you for your patience and understanding as we work to get as many young aviators in the air as possible!

We’ll see you at the Open House!

09/13/2026

Congratulations to Leo Brianas on passing his Private Pilot checkride!

Leo has worked hard to earn his wings, studying under Chris Criswell. We are so proud of you and can't wait to see where you fly to next.