If I Taught a Masterclass on Trails

My nine lessons on how a trail becomes the heart of a community

Tom imagines what his masterclass might look like along the trail

Winter in Ohio, especially this cold, icy, snowy one, has me doomscrolling more than I’d like to admit. The algorithm believes I need to take masterclasses, where experts share their secrets, and promise a no-fail formula for success. Apparently, you can master anything in less than an hour.

The algorithm also knows my surfing history, riddled with trails, cycling, the outdoors, and trail towns. I don’t consider myself enough of an expert to teach a masterclass. But on a cold, overcaffeinated day, I wondered what a Tom on the Trails version might look like.

A recent doomscroll led me to a video by Road Guy Rob about bike infrastructure on the Swamp Rabbit Trail, a trail I cycled in 2025. His words perfectly aligned with my thoughts. Inspired by his message, I added a dose of my own trail “wisdom” and built a lesson plan.

What does it look like when a city embraces its trails? It looks like better health, thriving small businesses, and a new sense of freedom in the outdoors. This masterclass dives into that transformation. Let’s take a look at the Tom on the Trails lesson plan.

Lesson 1: Start with transformation

Trails have a way of turning places into something more, destinations. An abandoned rail corridor becomes an evening walk with the dog. A vacant storefront suddenly has café tables overflowing with cyclists. A downtown that has seen better days turns into a trail’s town center where people linger.

This is a transformation, both subtle and dramatic. It’s not about budgets, land deals, and engineering that need to be figured out. Important, but the trail’s seed is planted with possibilities. When people can see what could be, they wake up. Tell that story well, and the rest will follow.

Lesson takeaway: Talk about transformations, the lives and communities changed, rather than the pavement and cost. That will come later.

Lesson 2: Build and share the vision

Every trail begins pretty much the same. Someone looks at an overgrown land ripe for reinvention. Beyond the weeds and rusted rails, they see it as something better, something valuable. It’s rarely only one person. A group grows, ideas bounce around, and a clearer picture emerges.

People don’t support projects. They support possibilities. A shared vision turns a trail project into a morning stroll, a safe commute, or a peaceful respite in nature. When the community imagines the experience, they fight for the result.

Building that vision takes patience, allowing people to look past their vision to make room for something bigger. The “We’ve always done it this way” or “We’ll never find the money” are normal, healthy concerns. Listen while working towards a shared vision to answer and overcome them.

Lesson takeaway: When people see themselves on the trail, it’s less abstract and more personal. And personal spreads.

Lesson 3: Partnerships make it real

A vision gets things started, but partnerships make them real. A trail serves many audiences. It’s an economic engine for the shop owner, a fitness center for the health advocate, and a destination for the tourism director.

To succeed, speak the language of the people drawn to the trail. These connections multiply. One partnership opens doors to a network of partners’ partners, turning an effort into a movement. With strong partnerships, there will be a crowd behind you by the time you reach the ribbon-cutting.

Lesson Takeaway: Every new partner is the key to many others.

Lesson 4: Expect and work through the barriers

Not everyone loves a trail. You’ll hear every objection: unsafe, too expensive, no one will use it, it’ll bring the wrong people. Barriers aren’t signs you’re failing. They’re just part of the conversation. Listen, especially to the loud voices you’d rather ignore.

Share the facts with empathy that invite people to help solve the problem. Sometimes you won’t win everyone over. That’s okay. People mostly want to feel heard. Funny enough, the things folks worry about most, safety, connection, and community pride, are exactly what trails end up improving.

Lesson Takeaway: When people feel valued, barriers are solved and not dead ends.

Lesson 5: Make it for everyone

Is it a bike trail, a shared-use path, or a multi-use trail? Language matters. When signs and publicity focus only on cyclists, the message gets muddled or worse, exclusionary. It suggests that walkers, birders, and neighbors using mobility devices are somehow less welcome than people on two wheels.

To turn the seemingly unmovable skeptic into a trail user by speaking their language. Show trail love by hosting events and highlighting stories that don’t always involve a bicycle. Keep everyone in mind when planning amenities and publicity. Once someone feels valued on the trail, the bike trail label disappears, and they become frequent visitors and supporters.

Lesson Takeaway: Use every means to say “You belong and are welcome here”.

Lesson 6: The Care Team

When you see a line out the door at the bike shop and a full trailhead, you know you’ve succeeded. But success requires maintenance, not just trail maintenance, but experience maintenance.

This is the role of the Care Team. It’s a mix of local business owners, the visitor center, service clubs, a friends-of-the-trail group, and residents who look after the small details. A shady bench, clear safety and wayfinding signs, and simple mileage markers tell travelers they’re welcome and safe. This hospitality transforms a trail into a community treasure.

Lesson Takeaway: Good trails are planned, but great trails care about the visitor.

Lesson 7: Build a network, not a trail

Most trails start small, connecting neighborhoods, towns, or suburbs. As time passes, the demand for connecting more grows. Eventually, a shift happens where the trail stops searching for connections, and the connections start searching for the trail.

Suddenly, developers, conservancies, and neighboring counties all want a seat at the table. Be open to seeing every conversation as an opportunity. Each new mile, trailhead, or gateway multiplies the audience and expands the impact. The doors to economic growth and tourism swing wide open.

Lesson Takeaway: Look beyond the next mile. Build a network.

Lesson 8: Tell the story

This might be the most important lesson of all. Trails don’t sell themselves. Stories do. The story of a small shop that went viral. A downtown featured in a national top-ten list. A cancer survivor’s charity walk was their second chance at life. Those are moments people remember. Those are the moments that make people want to be part of it.

Explain what the trail means to your town and community members. People connect the dots when it’s inviting and memorable. Stories move people in ways beyond a rack card or brochure they pick up. They resonate and invite.

Lesson Takeaway: Stories open the trail’s door. That’s what invites people in.

Lesson 9: Take the class home

In the end, this class isn’t really about trails. It’s about people. Start with the transformation and paint a vision that others can see themselves in. Build partnerships. Listen through the barriers. Make everyone feel welcome. Care for the small details. Think beyond a trail to build a network. Always, always tell the stories that showcase the heart of the trail.

If you want a great example of all this in action, watch Road Guy Rob’s Greenville’s Swamp Rabbit Trail video, South Carolina’s Freeway for Bikes. You can see the vision, the partnerships, the skepticism, the transformation, all playing out in real time.

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About the author

Tom writes Tom on the Trails, a newsletter about bikes, trails, and whatever he notices between one trailhead and the next. He believes trails change places for the better. Mostly, he’s just telling stories from the ride.