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Known as the Mother Road or Main Street of America, Route 66 is the most famous road in the U.S. and has played a major part in our nation's history. Starts in Chicago, this iconic road runs through the states of Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and finally California where it ends at the Santa Monica Pier. While many have driven the Route 66 by car, it's a whole other experience to do it on a bicycle. Welcome to Route 66 Bike Race, a 2,485-mile fully self-supported bike race that runs along the historic route. What's more exciting is that Topanga Creek Outpost's owner Chris Kelly has taken on the challenge to participate in the race.

An outdoorsman at heart, Chris takes every chance he gets to go on an adventure and thus created the UnPredict Your Wednesday weekly bikepacking trip. But running a small business for the last 16 years has not allowed him to go on epic adventures such as the Route 66 Bike Race. Finally now Chris gets the opportunity to follow his dream. His new journey started with a 3-day Amtrak train ride headed for Chicago for the official race start on October 1. Chris' goal is not to win the bike race but to truly enjoy every moment he's out there with his bike, a custom 27.5 Surly World Troller. With every pedal stroke he gets to deeply immerse himself in this unique and utterly colorful history of our nation.

I will be gone for a little over a month and I am really looking forward to riding my bike with not much else to do in October. When I first moved to LA, I didn't have a car, I rode everyday and I miss those days. I have a train ticket to Chicago and I will be headed back on Route 66 at about 100 miles a day for the Route 66 Bike Race 2485 miles back to Santa Monica.

So much is going through my mind, it is hard to concentrate. I am not great at planning for myself and I certainly didn't train enough. I could write on and on about my fears, I sorta feel like everyone on their first Saturday ride, wondering how they will do. Admittedly, I go through the same thing on all my bikepacking trips including UnPredict Your Wednesday and it turns out I usually survive fine. Stop by on Adventure Night to see the bike, hear about my gear and have fun and see for yourself my lack of preparations.

While our social media rides and UnPredict Your Wednesday looks like we just have fun, we work hard and I know while am gone it means working even harder, when it might not be possible. As I do this trip for a month, I am very aware of the impact my absence will have on others. Eric will be taking on the burden of Rover everyday including his usual Saturday pitch-in to help at the shop and navigating the website. Jeovany will be picking up much of the slack during our normal business days when he isn't at school. I appreciate Jeo's work and extra work, he has been doing the majority of the emails lately and a whole slew of projects in the "Important but not urgent category", the one I keep passing by. Perhaps the largest burden will fall on Jay, who will both tend to the shop on a day to day basis, do his normal hard work, and will be making all the decisions with the myriad of things small business is attacked with on a day to day basis. When someone isn't around to bounce off those decisions, it can be a great pressure. With the said, I super appreciate Jay's unflappable effort and spirit to find solutions during the darkest moments and the brightest ones. I am leaving the place in the most excellent hands. I have always said that my secret is surrounding myself with amazing people and taking off for a month leaving the Outpost in their most capable hands is a luxury few small business owners could possibly enjoy. A giant shout out to them a million times over for encouraging me to do this.

Chris riding the Surly World Troller in Route 66 Bike Race

My Bike Packing Gear:

  • Revelate Viscacha seatbag
  • Topanga Creek/Nuclear Sunrise Silo Bag (2)
  • Apidura Toptube bag
  • Revelate Jerrycan
  • Salsa Anything Cage (2)
  • Salsa Revelate Frame Bag
  • Bedrock Bag Handlebar Pouch
  • Bern Morrison helmet
  • Ortlieb Backpack
  • Outdoor Research Ultralight Dry Sack, 15 Liters
  • PrimaLoft Sleeping Pad
  • Outdoor Research Alpine Bivy
  • GoLite Sleeping Bag
  • Arizona Rafting Adventure coffee thermal
Chris in Kitsbow Icon wool shirt


  • Topanga Creek Outpost Long Sleeve Tech Shirt
  • Topanga Creek Outpost Short Sleeve Tech Shirt
  • SmartWool Short Sleeve Shirt
  • SmartWool Bottom Base Layer
  • TravelSmith Pants
  • Kitsbow/Topanga Creek Pendleton Icon Wool Shirt
  • Kitsbow Santini Bib
  • SmartWool socks
  • Topanga Creek Outpost Wool Socks
  • Patagonia Insulated Vest
  • Kelty Rain Jacket
  • LL Bean Slippers
  • TOMS Alpargata Slip-on Shoes
  • LA Bicycle Coffee Cap
  • Chuey Wool Cap
  • Buff Headwear Bandana
  • Louis Garneau Granite MTB Shoes
Chris camping with his tent at sundown.


  • Spot Personal Tracker
  • Chain links
  • Spare brake pads (2)
  • Spare tubes (2)
  • Zip ties
  • Patch kit
  • Multi-tool with chain breaker
  • Lezyne pump
  • Extra straps
  • Sun block
  • External battery for charging
  • Garmen Etrex 30
  • iPhone
  • Light & Motion Solite 250 EX headlight
  • Tail light (3)
  • Cash
  • Driver license
  • Water bottles
  • Spare cleats
  • Paper maps
  • S&S Coupler wrench

Find out what we're up to