Event Day Schedule

Saturday, July 25, 2026

8:00 AM20-Lap Event START

20-lap riders and 20-lap relay teams must check in with the registration table no later than 7:45 AM.

10:15 AM15-Lap Event Start

15-lap riders must check in with the registration table no later than 10:00 AM.

12:30 PM10-Lap Event START

10-lap riders must check in with the registration table no later than 12:15 PM.

3:00 PM5-Lap Event START

5-lap riders must check in with the registration table no later than 2:45 PM.

4:30 PM2-Lap Event START

2-lap riders must check in with the registration table no later than 4:15 PM.

5:00 PM1-lap Event START

1-lap riders must check in with the registration table no later than 4:45 PM.

5:30 PMAll Riders Begin to Finish

Gather 'round, gather 'round! All of the 1-, 2-, 5-, 10-, 15- and 20-lap riders should be coming over the Ride Like Ole finish line sometime around now (give or take 30-60 minutes)!

6:00 PMBBQ + good times!

Hang around as we celebrate each other's accomplishments, share high-fives with as many people as possible, and snack away on well deserved BBQ and enjoy good times together!

7:00 PMPrizes and Thank Yous

We'll thank all of the incredible people that made Ride Like Ole happen! Maybe you walk away with some awesome prizes?! You will be told how rad you were to come out and crush some trail goals! It'll be awesome, you won't want to miss this.

8:00 PMThe End (kind of)

Ride Like Ole doesn't really end, because after learning all about our friend Ole, we all simply carry on with a Live Like Ole mindset. Everyone comes away changed for the better. We hope this hits you like we know it did us and all those at last years RLO event. 💜

Register to Ride Like Ole!

  • Early Bird pricing in effect until midnight on June 30. Price increases $15 on July 1. 👉 Getting people excited about trails, encouraging everyone he was competing against, and making everyone feel like a rockstar was at the very heart of who Ole was. Bring the entire family out for a single lap bike ride of the approximately 5.4 km Ride Like Ole route and experience why Ole loved trails so much. Riders for this event will depart at 5:00 PM and join everyone back at the finish line for 6:00 PM.

  • Early Bird pricing in effect until midnight on June 30. Price increases $15 on July 1. 👉 If riding trails are new to you, Ole would want you to know that YOU GOT THIS! This 2 lap event is for those who want a great workout over around 10.8 km in the beautiful Squirrel Hills Trail Park. Bring your family and friends and have some fun within the beautiful festival vibes of Ride Like Ole! This event will start at 4:30 PM with an expected finish by 6:00 PM.

  • Early Bird pricing in effect until midnight on June 30. Price increases $15 on July 1. 👉 The 5-lap event is great for those who want to work their way up to the bigger Ride Like Ole distances. If the 10-, 15- and 20-lap events sound a little too crazy for this year, Ole would tell you this one is PERFECT for you! Riders in this event will cover up to 27 km of trail with roughly 450 m of elevation. The 5-lap event starts at 3:00 PM with an expected finish of 6:00 PM.

  • Early Bird pricing in effect until midnight on June 30. Price increases $15 on July 1. 👉 Not for the faint of heart, Ole might have described this 10-lap, as much as 54 km, 900 m of vertical version of Ride Like Ole, as "Just a fun ride!" Riders in this category should be relatively experienced cyclists and will begin their 10 laps at 12:30 PM with an expected finish of 6:00 PM.

  • Early Bird pricing in effect until midnight on June 30. Price increases $15 on July 1. 👉 So you're looking for more than the 10-lap "fun ride" but aren't quite sure if the 20-lap event is ready for an epic human like you?! 😉 Then Ole might say that this 15-lap, up to around 81 kms, 1350m of elevation adventure has "weekend plans" written all over it for ya! This event is for experienced riders that are used to long days in the saddle and can dig deep in order to do really hard things. This event starts at 10:15 AM and is expected to finish by 6:00 PM.

  • Early Bird pricing in effect until midnight on June 30. Price increases $15 on July 1. 👉 For those wanting to find the extreme outer limits of their abilities, the signature Ride Like Ole 20-lap event is one where Ole would surely have said "Oh, that looks AWESOME!" This event is for experienced riders only and will see participants completing 20 laps in the Squirrel Hills Trail Park, covering up to ~108 kms of sweet dirt single track with around 1800 m of elevation. This event starts at 8:00 AM and is expected to wrap up by 6:00 PM.

  • Early Bird pricing in effect until midnight on June 30. Price increases $15 on July 1. 👉 *NEW* this year is a 20-lap TEAM RELAY option where you and a group of friends take on the big 100+km/1800m challenge! Teams can be 2-5 people in size. Maybe you switch off with each other after every lap, or take turns doing double laps, or....whatever you'd like—the choice is yours! Each member of the team gets their own Ride Like Ole bike plate with lap decals assigned to each member based on the individual laps they rode. Your team will start with the main 20-lap event start at 8:00 AM and is expected to wrap up by 6:00 PM.

Team selection for 20-lap TEAM RELAY event only. 👇

Participant Info

Ride Like Ole Jerseys & Shirts (optional)

  • 2026 Ride Like Ole Tech T-shirt

    For 2026, the NEW shirt has taken a fresh step up in colour and vibrancy! We've also added Ole's Rules into a bike tire on the shirt back side. Like in previous years, this tech t-shirt features 100% performance polyester with wicking technology and is perfect for all of your ride, run and hike adventures. Standard, Ladies and Youth sizes available. All shirts available to PRE-ORDER only.

  • Ride Like Ole "Formal Dirt" MTB Jersey

    This uniquely Ole jersey, designed by Canadian jersey designer RiderMTB Clothing, in button up collared format with a slick "Gummy Stash" front pocket, features Ole's rules written in trail form across the shirt by Ole's sister Ava. Ole's silhouette sits on the right side with his hair flowing around to the backside, along with sleeves in two great colours, sure to catch lots of attention on the trail. These button up shirts are designed for a loose casual fit, so when purchasing, please note specific sizing information listed for each variant (Standard Unisex and Ladies cut). Limited quantities only (inventory as marked), available while supplies last (quantity remaining listed beside each size).

  • 2025 ORANGE Ride Like Ole Tech T-shirt

    Blowout Price on previous event inventory! Featuring Ride Like Ole artwork by Ole's sister Ava, this tech t-shirt features 100% performance polyester with wicking technology and is perfect for all of your ride, run and hike adventures. Limited Standard, Ladies and Youth sizes available. LIMITED quantities available. When clearout shirts have been sold they will not be restocked.

  • 2024 GREY Ride Like Ole Tech T-shirt

    Blowout Price on previous event inventory! Featuring Ride Like Ole artwork by Ole's sister Ava, this tech t-shirt features 100% performance polyester with wicking technology and is perfect for all of your ride, run and hike adventures. Limited Standard, Ladies and Youth sizes available. LIMITED quantities available. When clearout shirts have been sold they will not be restocked.

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A signed waiver by all event participants or parent/guardian will be required before your registration is finalized. A link to obtain and sign waivers for all registrants will be shown on the confirmation page and will be emailed to you.

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