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Deep Dive: RAGBRAI with Ride Director Matt Phippen

Iowa's biggest summer tradition is 13 days out, and we sat down with the man steering it all. Matt Phippen has served as RAGBRAI Ride Director since January 2022, guiding what's known as the oldest, longest, and largest recreational bicycle touring event in the world across the state each July. This will be his fifth ride at the helm.   Phippen grew up in Oelwein, where his parents once hosted a ride team that pitched 50 tents in their front yard during a 1990 overnight stop. That childhood memory hooked him for life, even though his own first RAGBRAI ride in 1998 was, in his words, "the worst experience of my life." 

Before taking the reins, Phippen managed the cycling division at Scheels sporting goods, joining the annual June route-inspection rides that precede every RAGBRAI. Now he's the guy who took riders off-route into Minnesota for the first time in event history, opened up Iowa's gravel roads to the pack, and launched new weekend rides that spread the RAGBRAI spirit statewide well beyond its official week.

In this wide-ranging conversation, Matt breaks down:

• What RAGBRAI really is — Iowa's rolling family reunion, connecting small towns of 70 people to riders from 50 states and 20 countries, plus the unscripted magic of it (like the year he ended up selling ice cream out of the back of a Peppy's van in Waterloo)
• The safety machinery behind the fun — how RAGBRAI's relationship with Iowa State Patrol, DOT, and county law enforcement starts every September, why 20,000 registered riders really means planning for 40,000 people on the road, and the "super sag" protocol (semis, school buses, and staged pickup points) built after the grueling 50th-anniversary ride
• A day in the life of the director — up at 3–4 a.m., waking Dream Team kids with a cowbell before sunrise, then riding the route town to town in a state trooper's cruiser until the last riders roll in at night
• Dream Team — the youth cycling program that pairs kids from all backgrounds with mentors, gifts them a bike if they complete training rides and RAGBRAI itself, and gives Matt one of his favorite parts of the day
• His fingerprint on the ride — expanding gravel routes across the whole week, and the story behind taking RAGBRAI across the border into Minnesota for the first time, including the logistics nightmare (and reward) of coordinating two states' worth of troopers, ambulances, and vendors
• Celebrities, politicians, and the "20,000 celebrities" line — how RAGBRAI handles VIP requests without turning into a political event, and why guests from David Robinson to Patrick Dempsey have quietly blended in with the pack
• The evolution of RAGBRAI's culture — from the harder-partying "Animal House" years of the '80s and '90s to today's more family-friendly ride, and how Matt's approach has changed the relationship between riders, law enforcement, and host towns
• Rig-of-the-week stories — from decrepit yellow school buses to six-figure RVs towing Jeeps towing side-by-sides, and the time a support-crew wife got an RV "high-sided" on the bike route and raced the tow truck to fix it before her husband rolled through

Grab your helmet, fill your water bottles, and — if you're in spandex — know that this is a judgment-free zone. It's RAGBRAI, straight from the ringmaster himself.

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