It’s see you later, not goodbye!
As one of our favorite CFIs, Caleb, has transitioned into an exciting new opportunity in aviation, we want to take a moment to highlight his aviation journey, how much we have enjoyed having him at Monadnock Choppers and the impact he’s had on our community! Caleb’s passion for tailwheel and precision flying stood out from the start. He helped countless students not only gain their tailwheel endorsements, but also build true confidence and proficiency in the aircraft. He also guided three students—John, David, and Caedan—through the full journey to becoming private pilots and supported many others in earning their high-performance endorsements. What truly set Caleb apart as an instructor was his commitment to growth—constantly working to improve himself both as a pilot and an instructor for his students. Outside of instruction, Caleb brought a strong spirit of community—whether it was heading off on aviation adventures like Sun ’n Fun, volunteering his time at Young Eagles, sunset Champin’ flights with Amy, or zipping around the hangar on the one wheel with Willie and Daisy. We’re incredibly grateful for his time here and wish him the very best in this next chapter. We hope you enjoy learning a bit more about him in this post!
Building from the ground up: From construction to the cockpit.
Caleb’s journey into aviation was not conventional. After years of service in the Vermont Army National Guard, he first considered transitioning into the world of aviation. His background in leadership and operations grounded him in the discipline, interpersonal skills, and attention to detail that define his flying style and growth in the industry.
Caleb worked in various roles in construction for 10 years. One of his supervisors owned a helicopter and could frequently be seen flying in and out of job sites. It turned out, his supervisor was the uncle of Monadnock Choppers Owner, Kevin, which ultimately led Caleb to pursue aviation more seriously. Because of his background in construction, Caleb took to hands on flying extremely quickly. Professionals in construction often excel in aviation due to their strong hand-eye coordination, problem-solving skills, attention to detail, and ability to work under pressure—qualities essential for both fields.
Caleb obtained the majority of his ratings “home grown” at Monadnock Choppers while working full-time. He was able to utilize the ArmyIgnitED program for support with his initial license, and he highly encourages military personnel to take advantage of this program. Caleb mainly used his pilot’s license to visit his family all over New England and for adventures with his friends before deciding to move into aviation as a full-time career. He understands the challenge of balancing work, flight training, and life, and passes this on to his students. Now you will find him guiding others on their aviation journey, usually with one or both of his his trusty pups, Willie and Daisy, as his co-pilot!
Passion for Teaching, Tailwheel Mastery, and Student Growth
As a Certified Flight Instructor (CFI) at Monadnock Choppers LLC, Caleb teaches all ratings and levels of students but especially enjoys teaching advanced training. He has has found his calling in teaching tailwheel instruction. Tailwheel flying is a foundational skill that refines a pilot’s ability to feel and control an aircraft. It demands finesse, precision, and a deep understanding of aircraft behavior—qualities that make a well-rounded and skilled aviator. Caleb focuses on helping students develop these essential skills, ensuring they leave his lessons as more competent and confident pilots.
Teaching Philosophy: Building Confidence and Skill
Caleb believes that every student learns at their own pace, and his teaching philosophy is centered on patience, structured skill development and maximizing the student’s investment. He emphasizes hands-on learning, ensuring that students develop muscle memory and intuitive control over their aircraft. His goal is to create skilled, confident pilots who are not only proficient but also have exemplary risk management and decision-making skills. Most importantly, Caleb wants his students to always maintain a passion for aviation and encourages them to constantly expand their skillset and experiences whether it is tailwheel flying, high performance/complex endorsements, or seaplane ratings.
Sharing the Joy of Flight Through Volunteering
Beyond the cockpit, Caleb uses aviation to give back to the community. He volunteers with the Young Eagles program, inspiring the next generation of pilots by offering them their first taste of flight. He also dedicates time to Angel Flight, providing free air transportation for patients and their families in need of medical care. He is also the first person to sign-up to participate in outreach events such as Family Day at Allyson’s Orchard and share his passion for aviation.
Life Beyond Aviation: Nature, Dogs, and Tiny House Living
When he’s not in the sky, it’s hard to keep Caleb indoors! An avid hiker, he loves exploring rugged trails, always accompanied by his dogs and Amy. He’s a lifelong snowboarder and has helped maintain the ski trails for various mountains. He took great pride in building a tiny house and traveled all over New England for enjoyment and flight training.
What’s Next?
Whether he's teaching students to finesse their tailwheel landings, mentoring young aviation enthusiasts, or embarking on a new hiking adventure, Caleb embodies the spirit of adventure and generosity. Caleb has made his next steps in aviation which are to instruct as a CFI at Goodspeed Seaplanes and continue building his skillset and flight time to qualify for more advanced flying jobs. He’ll always be part of the Monadnock Choppers crew, and will continue to provide support and advice to our Monadnock Choppers family. We look forward to our students having a place to go for a seaplane rating and watching Caleb grow and excel in his career! Congratulations Caleb!
