39 Airports, 1 Grand Adventure

Seventy-four-day Cirrus journey focuses on growing real-world pilot skills.

Monday, April 13, 2026 at 08:00 AM ET

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Pilot Blake Freedland (right) and co-captain Dylan Tamaroff flew across the U.S. and Canada in a Cirrus SR22. [Credit: Blake Freedland]

Key Takeaways:

Two pilots undertook a 74-day, 13,000 sm cross-country flight in a Cirrus SR22 across the U.S. and Canada, visiting 39 diverse airports to gain experience and explore.
The journey exposed them to unique and challenging airports, leading to key lessons about flexible planning (favoring regional bases over fixed itineraries).
Crucially, continuous support from aviation experts and navigating varied terrain, weather, and airspace significantly enhanced their piloting proficiency, confidence, and safety skills.

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Like most pilots, I’ve always dreamed of a grand trip. A shared passion for challenge, adventure, and flying eventually drives all of us avgeeks to leave our comfort zones and explore.

So, to celebrate our graduation from Tufts University and Berklee College of Music in Massachusetts, I decided to fly across the U.S. and parts of Canada in my Cirrus SR22 with one of my best friends and copilot, Dylan Tamaroff. Our goal was to see new places, meet people, discover hidden gems, and most importantly, learn. I wanted to push myself, sharpen my skills, and become a better aviator.