About
We help families find a calmer, more patient way forward when teaching a child to ride has become harder than it should be.
Pirate Skool exists for the family behind the rider. The person who calls is often a mother who has tried the driveway, searched for answers, and is still looking for a way to make riding possible. Sometimes it is both parents, a father, or a grandmother. The common thread is care and persistence. They want their child to have more independence and the same ordinary freedom as other kids — a friend’s house, keeping up with a sibling, joining the ride.
You do not have to be the teacher. We can take the next bike step together.
Some children need more time, a quieter place, or a different way in. Their parents want a patient instructor who pays attention to the child in front of him, not a one-size-fits-all lesson. The lesson should fit your child.
If you are wondering whether this is a fit, give us a call so we can learn more about your child.
For some children, the fear has become bigger than the bike. A fall, a bad first try, or being pushed too fast can make getting on feel impossible. The parent may be tired of being the coach, the cheerleader, and the person holding the bike.
Fear is a place to start, not a character flaw. No forcing. No audience. No pretending the first step is easy. If getting on feels impossible, start with a call. We’ll listen and help plan the first step.
Other children are willing but need a teacher who is not their parent. You do not have to be the coach. Sometimes a child just needs a different person to show them the way. Bring the child. We will bring the bikes and a clear plan.
If fear is not the main issue and your child is ready to try, book the lesson and get one more thing off your list.
Pete Conway has been teaching people to ride for more than thirty years. Pirate Skool is the current form of that work: private lessons in quiet lots around Topsfield, Massachusetts.
He is a cyclist, a teacher, and a parent. He started the bike school because riding a bike is one of the few skills that gives a child more independence and a way to join in. Families kept arriving after a fall, a bad first try, or a few too many hard afternoons in the driveway. The method got more precise. Each rider brought a different starting point. The offer got simpler: one instructor, one rider, the right bike.
We’ve taught hundreds of kids to start, stop, pedal, and steer in a quiet lot, then build from there.
The recipe is simple: a quiet lot, a right-size bike, and an instructor who can stay with the student. For kids with special needs or high fear, give us a call.
If your child just needs a nudge, book a lesson.
Hear Pete tell the origin story on the New England Endurance podcast.
We teach kids 5 and up. We don’t work with children under 5.
The crew
Head Instructor & Founder
Pete founded Pirate Skool after decades of teaching people to ride. Parents call him calm, patient, and oddly fast at getting a stuck kid rolling. He works 1:1 in quiet lots, starts on the right-size bike, and treats fear and extra needs as part of the work — not a special exception.
“Be awesome.”
Owner & Operations
Lucy brings a healthcare background, a lifelong habit of moving outdoors, and the practical care that lets families show up and focus on the lesson.
“I ain't here on business, baby, I'm only here for fun.”
Director of Operations
Nefer handles everything that is not happening in the parking lot or on the medical side — the site, the systems, and the work that lets our instructors stay with the student.
“West side till I DIE!”
First Mate & Chief of Snacks
Buddy does not teach lessons. He is the welcome committee, the parking-lot supervisor, and the reason the parrot stays on someone’s shoulder instead of in a tree. His official duties are looking unimpressed, accepting tribute, and reminding nervous riders that at least they are not wearing an eyepatch to work.
“The treasure was snacks. We knew that.”
Talk first
Tell us the child’s age and anything that helps the first lesson go well. You do not need to share a diagnosis here.
