Getting into Group Rides: A Quick Start Guide

So, you want to do your first group ride but don’t know where to start?

Fantastic. Let’s chat.

Riding bikes with other people—also known as going on a group ride—can feel daunting at first, but it’s an incredibly important part of your journey on two wheels.

Think of it like learning a language. You can study vocabulary and grammar all day long, but if you never practice speaking with others, it’ll always feel unfinished. The same goes for riding: solo rides are great—been there, done that—but the joy of connecting, building community, and just vibing with others on bikes? That’s the whole point.

So, where do you start?

In this post, we’ll follow Anastasia’s story to show how progressing from one group ride to another can help you push your limits and stack small wins along the way.

Step 1: Get a bike that fits

Not necessarily one that’s super light or high-end. Just something that fits you—not too big, not too small. Ideally, it has a few gears, but single speeds are totally fine to start with.

Anastasia started out with a $10 Huffy she found online. There’s nothing inherently wrong with a $10 bike—but chances are, it won’t be a great experience. If the ride is so uncomfortable it makes you hate riding, it might be time to find a bike that sucks just a little less.

And that’s what she did. She scored a sweet road bike for $250 from a friend she met on the Crank Arm ride. Which brings us to...

Step 2: Find the casual ride in town

Most towns have a casual ride. If they don’t—start one! Lauren and I started The Wednesday Ride in Colorado Springs after realizing there were no chill rides in town. Turns out, people love that vibe. Now, it’s 50+ riders deep every week.

Casual rides teach you how to ride around other people in a not-so-organized fashion. That may sound chaotic (and it is), but it’s a crucial first step toward more cohesive, faster-paced rides. Learning to move in a group is a real skill.

Anastasia started showing up to the Crank Arm ride every Wednesday and quickly got more comfortable riding in a big pack. I remember her first one—riding way off the back, nervous about crashing. Fast forward a few months, and she’s in the middle of the mix, riding one-handed, big chillin.

And remember, the right bike makes maneuvering much easier. See Step 1—fit is key!

Step 3: Try another ride

Maybe it’s a monthly ride like Critical Mass, or a themed one like the Third Thursday Cruiser with Oak City Cycling. Or maybe it’s just another weekly ride, like the Espresso Express.

Trying different rides helps you figure out what you vibe with. Some might not be your scene. Some will feel just right. You won’t know until you try.

Anastasia started riding in Critical Mass after we brought it back last May. It’s a monthly ride (happening this Friday, March 28th!) and a great chance to show the city just how many of us are out here riding.

Step 4: Upgrade when it makes sense

Not all bikes are built for all group rides. Some rides go through Umstead—road bikes usually can’t handle that. Others might cruise through Crabtree—you’ll probably want a mountain bike for that.

On the flip side, if you started on a mountain bike, you might struggle to keep up on road rides like Jubala, Burial, IOS, or RBC. These faster-paced rides are awesome, but having the right bike matters.

And yes, chances are, you might get dropped. That happens to everyone who’s brave enough to try a fast ride. Getting dropped is practically a rite of passage. But the next time you hit that redline, you’ll hang on a little longer—because riding home alone isn’t the most fun.

Anastasia? Like the real G she is, she got dropped on her first Jubala ride. Second time? Better. Third time? Even better. That’s how it goes.

It never gets easier. You just get better. And the reward for all that effort? Teddy Roosevelt nailed it in his lesser-known speech Citizenship in a Republic:

“...at the best knows in the end the triumph of high achievement, and who at the worst, if they fail, at least fail while daring greatly, so that their place shall never be with those cold and timid souls who neither know victory nor defeat.”

Let’s ride.