Off the beaten path

Three festivals that still feel like the best version of what a festival is supposed to be and happen to have incredible riding right outside of town.

Somewhere along the way, the big music festival machine started feeling a little hollow. The crowds got bigger, the ticket prices got wilder, and the whole thing started to feel more like a brand activation than a genuine gathering. But the antidote has always been out there. Smaller, slower, realer. The kind of festival where you camp on the grass, strike up a conversation with the strangers next to you, and realize by Saturday night that you have made actual friends. Where the food comes from someone's family recipe and the music comes from artists who still load their own gear. Where the whole thing feels handmade, because it is.

Those are the festivals worth building a trip around. And if you ride bikes, which you do, the best ones tend to sit right in the middle of some quietly exceptional trail country. Here are three that fit that description perfectly, along with the Club Ride pieces that will carry you from the dirt to the dance floor without a second thought.

01

Sisters, Oregon

Big Ponderoo Music and Art Festival — late June, Village Green Park

Riding: Gravel and Mountain Biking  |  Music: Americana / Bluegrass / Alt-Country

Sisters, Oregon is one of those places that gets it right on every count. The Old West-themed downtown sits at the foot of the Three Sisters peaks, surrounded by dense ponderosa pine forests and high desert landscape that practically begs to be explored by bike. The Peterson Ridge Trail system, over 25 miles of flowy singletrack right on the edge of town, is a local treasure that draws riders from across the Pacific Northwest. Gravel fans get an extensive network of forest service roads stretching in every direction through volcanic terrain, lava fields, and river valleys, with routes ranging from 20 to 50-plus miles.

Then there's Big Ponderoo, a joyful, independent, nonprofit two-day festival that describes itself as "a festival reminiscent of the days before the corporate music monopoly took over." Produced by SFF Presents, the same people behind the long-running Sisters Folk Festival, Big Ponderoo sets up two outdoor stages under the signature ponderosa pines of Village Green Park right in the center of downtown. The lineup leans into Americana, newgrass, alt-country, and blues, with artists like the Hogslop String Band, The Brothers Comatose, Fruition, and the Fireside Collective taking the stage. They even offer a free bike valet. It's an all-ages, blanket-and-lawn-chair affair with camping nearby at Indian Ford Campground and on surrounding National Forest land. Exactly the vibe you're looking for.

02

South Hiram, Maine

Ossipee Valley Music Festival — late July, Ossipee Valley Fairgrounds

Riding: Mountain Biking and Gravel  |  Music: Bluegrass / Roots / Americana / Folk

Hiram, Maine isn't exactly on the radar, and that's precisely the point. Tucked in the western foothills of Maine, less than an hour from Portland and just across the border from North Conway, New Hampshire, this corner of New England is quietly spectacular. North Conway has become one of the Northeast's premier mountain biking destinations, with over 1,200 miles of trails threading through the White Mountain National Forest, a lift-served bike park at Cranmore Mountain Resort, and a trail-building community, Ride NoCo, that keeps raising the bar. Gravel riders have the Cross New Hampshire Adventure Trail and a web of quiet forest roads to explore in every direction.

The Ossipee Valley Music Festival happens on the banks of the Ossipee River, in the tall pines and goat barns of the fairgrounds, and it sells out every year, which tells you everything you need to know. Five stages over four days feature the best in roots, bluegrass, Americana, folk, and blues, with past headliners including JJ Grey and Mofro, The Wood Brothers, Sierra Hull, and Allison Russell. The campfire picking scene around the campground is its own attraction. Kids under 18 get in free. There's a barn dance. There's a flatpicking contest. It's that kind of festival, the kind you try to keep a secret but can't help telling your riding friends about.

03

Makanda, Illinois

Little Grassy Get Down — early fall, SIU Touch of Nature Outdoor Education Center

Riding: Mountain Biking and Gravel (Shawnee Forest)  |  Music: Acoustic Americana / Roots

Most people don't think of southern Illinois as a bike destination. That's a mistake. The Shawnee National Forest stretches across 280,000 acres of rugged, unexpected terrain. Sandstone bluffs, hardwood hollows, hidden lakes, and enough dirt road to keep a gravel rider busy for days. The area around Makanda and Carbondale has a growing trail network and a strong local riding community that keeps the secret close. It's the kind of riding that surprises you, technical in spots, wide-open in others, always scenic.

The Little Grassy Get Down is held at the SIU Touch of Nature Outdoor Education Center on Little Grassy Lake, surrounded by the forest, and it's about as low-key and genuine as festivals get. The lineup sticks to acoustic Americana from around the Midwest, with acts like Woodbox Gang, Chain Station, and Chicago Farmer, and three days of music, food, local vendors, hiking, biking, and tent or car camping right on site. It's not trying to be anything it isn't. Just good music in a good place with good people, which is exactly what the best ones are.

What all three of these festivals share is that they didn't happen by accident. A community wanted something real, built it from the ground up, and kept it true to itself. The riding nearby isn't incidental either. These are places where the outdoor life and the music life are part of the same culture. Show up in Club Ride. Fit right in.