Events & Tours

WinterOak Adventure Training

WinterOak offers 3 unique Adventure Motorcycle opportunities for all skill levels. Whether you’re an absolute beginner or an experienced rider that just doesn’t want to be bothered with the details. We have you covered!
Please note that a 50% deposit is required at the time of sign up, with the remaining amount due 7 days before event.

We are working hard in 2021 to complete our course! Please note, this is the year of construction therefore not all obstacles may be available during your class. 

We are willing to convert our immersion tour dates into classes if desired. Please inquire if this is something you are interested in!


$500 per person

Our beginners classes are all 3 days and 2 nights. We begin with basic riders skills and end our weekend riding the forest roads in our local counties if students are comfortable.


Friday, May 21st – May 23rd, 2021
Friday, June 4th – June 6th, 2021
Friday, August 13th – August 15th, 2021

Immersion Tours

$1600 per person

Our immersion tours are something we are very excited about this year! The tours start out as the next level up from our Basic Skills classes. We go over more advanced techniques and tips for the trails, Solo adventure gear, food prep, as well as, more advanced practice on our track. Immersion tours are 5 days and 4 nights. After our refresher day we begin making our way to the Northwoods. 


Friday, June 25th – June 29th, 2021
Friday, September 10th – September 14th, 2021


WinterOak strives to give the best guided tours we can! With complete group customisation we can go anywhere your group would like to. Growing up around hunting and fishing guides, not only do I guide the tour but also cook breakfast and a good campsite supper from local farms and homesteads. Preplanned tours also available covering the Arrowhead of Minnesota, Northwoods of Wisconsin and the UP of Michigan.

Dates & Prices

Thursday May 27th – June 1st, 2021 (Memorial Weekend) $1500 per person
Monday July 19th – July 25th, 2021 $1800 per person
Thursday August 19th – August 23rd, 2021 $1200 per person
Thursday September 16th – September 20th, 2021 $1200 per person
All of our services have a few things in common:
#1. Each participant is responsible for providing their own Motorcycle, with proper insurance.
#2. It is to your benefit that you properly equip your motorcycle with at minimum 60/40 tires; ie 60% off-road/ 40% pavement. It is under the discretion of WinterOak to turn you away from an event with NO REFUND if your tires do not meet our safety regulations.
#3. Every rider must (at minimum) come with basic riding gear such as DOT approved helmet, riding gloves, over the ankle riding boots and proper eye protection. These are just the minimum, it is up to each rider to further protect themselves.
#4. Each rider must come prepared with their own camping gear, such as: Tent, Sleeping bag, mess kit, hygiene kit, personal First Aid, casual clothing, etc.
#5. Each event will meet at WinterOak Homestead/Track.
#6. There are 3 tent platforms that must be reserved at the time you sign up for an event. Sharing platforms/tent is fine with prior notification. More camping space available if all platforms are reserved.
#7. For each day of our Tours and Immersion Tours, included in the cost, WinterOak will provide home cooked camp breakfast and supper. Each person is responsible for their own lunch. Supper will be provided for Basic Skills classes, restaurants and gas station 1.5 miles from our location.
#8. Each person is responsible for providing their own fuel.
#9. Due to wanting to provide the best experience possible for our guests, our classes and tours are limited to a maximum of 8 people but there are no minimums.
#10. Tour dates are flexible, classes and immersion tours are not.
#11. Shower, laundry, Motel facilities located at 29 Pines truck stop 1.5 miles away from our location.
#12. A deposit for 50% of the cost of the event is due upon sign up, with a full refund available up to 15 days from the date you sign up.  The remainder is due 7 business days before the event.  If you sign up less than 30 days from the date of the event the deposit is nonrefundable.
#13. Dietary Note: Homestead Style Camp Cooking.  At this time we are not able to accommodate vegan/vegetarian options.
#14. 2021 Season Events are unable to be switched to 2022.  Any rescheduling must be done in writing 30 days prior to the originally scheduled event.
#15. Refunds are at the desecration of WinterOak Moto Adventures
#16. There is no such thing as bad weather, only bad gear.  We ride rain or shine.  Our classes will only be canceled in the event of a Natural Disaster or Family Emergency.

Interested in an event or tour? Register now!

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