Where Should I Ride? If You Don't Know, You Won't Go

October 18, 2026 · National Ride Network

Most of the texts I get look the same. A member is headed to Chicago, Milwaukee, Madison, Tucson or St. Louis and wants to know where to ride. I've lived in a lot of these places and ridden a lot of roads, so I'm the person people ask.

Anyone can find a ride if they just want to be on a bike. Someone who texts me wants a good one. They care about the experience, not only the mileage. That's the reason NRN exists, and it's what this post is about: how to find the best ride in a place you don't know.

A route is more than a line

Most sites hand you a route and nothing else. No reason it goes where it goes, no history, no sense of what it's like to ride it.

When I build a route I make choices. I send you up a road with a view. I put the turn on the right side of the road so you aren't crossing traffic. Sometimes I take you a slightly odd way instead of the obvious straight line, because the odd way is better. Riders tell me afterward that they had a much better day than they'd have had on their own. That's the part that's hard to copy, and it's the part I care about most.

The feeling is what gets people to go. If you can picture the trees, the hill and the road you're about to be on, you want to be there.

The Double Barrel

The best example I have is one I rode myself.

The Shootout in Tucson is probably the most famous group ride in America. I rode it every weekend, early in the morning. The Double Barrel is the Shootout plus Mount Lemmon in the same day. I wrote that route, and I was one of the first people to ride it.

I hadn't planned it that day. I finished the Shootout, which was fast and hard, and rolled back to Mercado San Agustin in downtown Tucson. I had a Coke and a pastry, and a coffee at Presta. Sitting there, I decided to keep going. To get to the base of Lemmon I rode right past my house. I could have gone home, and I didn't.

I was already tired. It had been eight or nine hours. The forecast said a clear, warm day, so I had no winter gear. Then, near the top of Lemmon, it turned cold and a small storm came in. Snow flurries, and something close to hail, pin-sized and coming in hard, pelting me while I was finishing the climb. I'd used the rest of my two bottles getting up there, so I pulled into Summerhaven, filled up quickly, and went straight back down toward warmth. My fingers were almost frozen. Everything hurt. It got warmer toward the bottom, and getting home was a huge relief.

The numbers: 200 miles, 13,422 feet of climbing, 9 hours and 26 minutes. It's one of the biggest things I've done on a bike.

I've never been the strongest racer. I'm the guy who can suffer the longest. That day I had good legs and a good engine, and I loved how riding made me feel. I didn't plan the ride. I decided at a table in the Mercado, and I'd trained for that decision for a long time.

You can find the full route, with the start times, the sections and the safety notes, on the NRN route page.

Why riders don't go

When someone texts me, they haven't done anything wrong. They just don't know where to go. Our line is simple: if you don't know, you won't go.

So I try to take out everything that gets in the way:

• See it before you ride it. Tap a point of interest and you get Street View, so you know what the bathroom stop, the gas station or the bakery looks like before you arrive.
• Know the weather and the wind. Each route shows the forecast and a wind map overlay.
• See the terrain. The elevation profile pops out into a topographic view, so you can see what a climb actually looks like.
• Pick your map. Dark mode, satellite or hybrid.
• Take it with you. Send the route to your device, share it with your group, or save it as a PDF so the story, the stops and the safety notes are with you when you have no signal.
• Find the good stops. Partners and places along the route are right there on the page.

Some riders want the lowest price. Some want the feeling. Some want to dig into the data and look at how a climb is shaped. I want every one of them to be excited to go.

Where to eat, drink and sleep

I'm building this out city by city, and it's slow, because I only recommend places I've been. I want to know the coffee is the best coffee, with good beans, and that the place feels like an experience. You should be able to walk in and feel confident that the recommendation was right.

That isn't easy. Some of the best places are already well known, and a partnership doesn't offer them much, since people show up anyway. I'm still going to highlight the best things in each area.

The list can't be bought. If a place treats our members badly, has bad service or a bad product, I'll take it off, whoever they are.

Go

You don't need to know a place before you ride there. You need someone who has been, who will tell you why a route goes where it goes, and who wants you to have a great day.

Pick a city, pick a route, and go.