Learn to fly Tailwheel open up Maine's backcountry
From your first wheel landing to threading it into a grass strip in the Western Mountains, Tailfin builds confident and proficient tailwheel pilots for real-world experiences — not just a logbook entry.
Tailwheel time that's actually useful
A lot of endorsements end the day you get the logbook entry. Ours is built to be the start of something bigger — a real, staged path off the pavement and onto the kind of grass strips most pilots only hear about.
Built as a progression
The endorsement and grass strip proficiency are staged deliberately — the first builds the stick-and-rudder foundation, and the second takes it off the pavement and onto the kind of Maine strips that drew you to tailwheel flying in the first place.
Instruction from someone who's been in the woods
Michael Gaines is a CFII rated in both SEL and SES, with EMT training and real field time in conservation and Fish & Wildlife work. You're learning to fly off the pavement from an experienced professional who has actually done the work.
Real grass, close to home
Stage two works local grass strips around Auburn-Lewiston — soft- and rough-field technique, strip surveys, and go/no-go decisions, practiced on actual Maine turf instead of simulated on pavement.
Two stages, one runway to the next
Start wherever fits your logbook. Rates are $190/hr wet for the Cessna 140 plus $80/hr instruction; the prices below reflect a typical student.
Basic Tailwheel Endorsement
Your 61.31(i) endorsement, taught properly: wheel and three-point landings, crosswind technique, ground handling, and go-around discipline in a real taildragger — not a quick pattern-and-sign-off.
- Ground school on tailwheel aerodynamics and technique
- Three-point & wheel landings to proficiency
- Crosswind and gusty-condition handling
- Logbook endorsement on completion
Grass Strip Proficiency
For tailwheel pilots — Tailfin-trained or not — ready to take the endorsement off the pavement. We work local Maine grass strips on soft- and rough-field technique and the density-altitude judgment that pavement flying never teaches.
- Soft- and rough-field takeoff & landing technique
- Density altitude & performance planning
- Strip surveys and go/no-go decision-making
- Local grass strip circuit, Auburn-Lewiston area
Already tailwheel-rated elsewhere? Start here.
A Taildragger Built for Maine's Backcountry
Every stage is flown in the same Cessna 140 — a light, responsive taildragger that rewards precise footwork and sound judgment, the same skills that matter most once you're working a grass strip in the Western Mountains.
You'll fly this aircraft from your first three-point landing at Auburn-Lewiston through your most demanding grass-strip approach. One airplane, one standard of proficiency, and no surprises as the terrain gets tougher.
A few things people ask
Do I need to do both stages?
No. Most pilots start with the Basic Tailwheel Endorsement, but if you're already tailwheel-rated you can start straight into Grass Strip Proficiency. We'll talk through where you actually belong on the phone.
How is pricing actually billed?
$190/hr wet for the Cessna 140 plus $80/hr instruction. Package prices are estimates based on a typical student's hours, not a flat fee.
Do you fly year-round?
Scheduling depends on Maine weather and field conditions, especially for the grass strips. Call and we'll find the right window for your stage.
Ready to fly tailwheel?
The fastest way to get moving is a phone call — tell us where you are in your logbook and we'll tell you which stage to start on.
(207) 838-8927