About Us:
Clear Skies, Disciplined Training
At Driftless Aero, our mission is simple: provide high quality flight instruction that is tailored to each individual’s learning style, goals, and schedule. We understand that every student comes to aviation with different experiences, commitments, and aspirations, which is why we take a personalized approach to training. We believe earning a pilot certificate should be both attainable and affordable without ever compromising safety, professionalism, or the quality of instruction. In an industry often crowded with one size fits all solutions, Driftless Aero is committed to offering a flight training experience that simply makes sense. We are flexible, practical, customer-focused, and designed to help students succeed efficiently while building the skills and confidence needed to become safe, competent pilots.
Meet the Staff
Dakota Carden
Owner/CFI
Britney Boxrucker
Chief Flight Instructor
CFI/CFII
Originally from Barneveld WI, Dakota began Driftless Aero in the first part of 2024 when he saw a need for affordable flight training in the southwest Wisconsin area. He has been an instructor for over nine years and has accumulated thousands of hours of dual given. He is an ATP rated pilot and remains active in the training environment for the love of watching those "light bulb going off" moments with clients. His role outside of running the business surrounds specialty requests as well as mowing the grass around the hangar; his favorite job.
Jeremiah Pinch
Flight Instructor
CFI/CFII
Originally from Cassville WI, Britney joined Driftless Aero in 2024 and played a key role in the flight school's success. She set the tone for what quality and personalized flight training meant. She is a commercial pilot and soon to be ATP rated as she competes that final certificate later in summer 2026. Outside of flying, Britney has experience in airport management having ran airports as well as provide consulting services for local airport managers. Currently she oversees all of the daily operations as well as handles all of our Discovery Flight Lessons!
Originally from Madison WI, Jeremiah began working with Driftless Aero early in 2026. He has a background in customer service and aircraft handling making him the perfect candidate to help you with all of your aviation training needs! With a commercial pilot certificate and countless hours in Cessna and Piper aircraft, Jeremiah knows all of the tips and tricks to help you achieve your pilots ratings in a fast and effective manor. Hard work and a dedication to the client has proven to elevate him above the rest when it comes to flight instructors in our area. Jeremiah handles all of our daily flight instruction and can't wait to see you soon!
Testimonials
If you’re considering flight training, Driftless Aero is definitely worth your time. I spent a couple of months floundering with another instructor before switching, and once I started here, things really took off.
I was able to earn my Private Pilot License while working a full-time job, and I did it for far less than I ever expected. Driftless Aero makes learning to fly affordable and achievable for anyone with the slightest desire to do so. I believe that really comes down to the quality of instruction and how well they run their operation.
Britney is an excellent instructor who adapts her teaching to you, building real confidence and understanding with every aspect of flight. I am 47 years old, and I can honestly say they proved you’re never too late to learn something new. The strength and adaptability of their instructors is clearly a cornerstone of their commitment to students.
Their scheduling flexibility makes it easy to stay consistent, even if you have a demanding life schedule, and the aircraft is always well-maintained and ready to go. They also have a great system in place for seeing when the aircraft is available, which makes scheduling a breeze.
Most importantly, safety is front and center in every lesson. From pre-flight discipline to in-flight decision-making, they consistently reinforce the habits and mindset needed to be a responsible pilot.
If you’ve been thinking about learning to fly, reach out to Driftless Aero and get on the schedule. It’s more achievable than you think, and you’ll be in great hands.
-Brodie D
I have just completed my Biennial Flight Review with Britney B. at Driftless Aero at Iowa County (WI).
She is an awesome flight instructor! She is fun to work with and never intimidating. She is very knowledgeable, efficient and thorough. She clearly assesses your needs and then addresses them with sound recommendations. I have had many different instructors for BFRs over the years. Britney rises above them all - a genuine nice person! In addition, Iowa County Airport is ideal for instruction.
-Dennis S
I can't say enough good things about Driftless Aero! Britney and Dakota are such easygoing, fun people who make flying feel approachable and enjoyable right from the start. They're passionate about what they do, and it shows in every lesson.
I've been learning to fly with them in their Cessna 150 at a pace that actually fits my budget and schedule, which has been a game-changer. They’ve also created such an inviting environment for the ground training. Their lounge and classroom right in the hangar make even the “not-so-fun” parts feel comfortable and welcoming.
They also offer sightseeing flights for anyone who just wants an awesome experience in the air without committing to full flight training. My wife and son both did one and absolutely loved it!
If you're thinking about learning to fly or just want a memorable flight, this is the place to go. Highly recommend!
-Jordan C
I was looking for a creative anniversary gift and heard about Driftless Aero and I'm so glad I went with it as a surprise. It was a fun, unique experience for my hubby... and the best part- he actually got to fly the plane for most of the flight.
It was something totally different, memorable, and fun! If you're looking for a gift that is out of the box and full of an adventure, I would highly recommend!
-Dawn M