Planning a Weekend Ride with Friends Who All Ride Differently

You want to ride. Your friends want to ride. But suddenly it’s complicated.

One of you has a gravel bike and a heart rate monitor. One’s on an e-bike. Someone else only rides in cutoffs and Birkenstocks. And there's always that one guy who shows up on a single-speed because “gears are a conspiracy.”

Wrench and Roll crew on a roll

We’ve been there. At Wrench & Roll, we’ve helped plan group rides for families, friend groups, coworkers, and full-on community events. If you’ve got people with different speeds, bikes, and energy levels but still want to ride together, here’s how to make it actually fun (and not a rolling argument).

Pick a Route That’s Forgiving

Start with something flat-ish and flexible. The La Crosse River State Trail is a classic—wide, well-marked, and chill enough for just about anyone. Want a view? Riverside Park to Pettibone and back is a great out-and-back loop that doesn’t require full leg commitment.

Keep it under 15 miles if you're riding with someone who's new to biking or on a cruiser. If people want more, they can always add extra miles after the main ride.

Not sure where to ride? We’ve mapped out a few of our favorite loops on our Bike La Crosse page or just come into the shop and we’ll help you plan something that fits your crew.

Agree on the Vibe Ahead of Time

This part matters. Is the ride about exercise? Scenery? Coffee stops? All three?

Make sure everyone’s on the same page before someone shows up in clip-ins ready to sprint. It sounds obvious, but nothing tanks a ride faster than mismatched expectations.

We always say: it’s better to go a little slower together than to ride fast alone.

Build in Breaks (and Snacks)

Even if your whole group is in decent shape, someone’s going to need a snack, a stretch, or a water break at some point. Plan them in. Picnic benches at Myrick Park, coffee stops downtown, or just shady trailheads make good regroup spots.

Pro tip: stash some energy chews or granola in your saddlebag. We sell a few solid options in store if you want to stock up before your ride.

And if someone in your crew needs to rent a bike for the day, check out our bike rentals. We’ve got cruisers, e-bikes, hybrids—whatever fits the group vibe.

Let the E-Bike Go First (Sometimes)

If someone’s on an e-bike, they’re probably going to have a good time no matter what. But that doesn’t mean they should leave everyone in the dust.

Instead of trying to match speed, take turns leading. Let the e-bike rider scout ahead if there’s a tricky intersection, then have them loop back or wait up. It keeps the group together without making anyone feel like they’re dragging or flying solo.

Need help figuring out if your e-bike is ready for a long ride? We can run a quick check on your battery and drivetrain so you don’t end up pedaling 40 pounds uphill with no assist.

Make It About the Experience

The best group rides aren’t about the distance or the stats—they’re about the dumb conversations, the weird roadside stops, and the shared effort. So lean into it.

Ride slower. Laugh louder. Stop for ice cream. And if someone forgets their helmet or shows up with an actual boom box bungee-corded to their rack, just roll with it.

Not sure your bike’s up for the weekend? Come talk to us. We’ll make sure your tires are full, your gears are shifting, and your group ride doesn’t turn into a group walk.