I don't just guide the trails—I curate the ultimate weekend escape. 

Winston's Expeditions LLC was founded to eliminate the chaos, dust, and logistics of traditional group rides. We replace crowded campgrounds and frozen meals with an elite, small-group backcountry vacation centered around premier trail curation, absolute safety, and top-tier lodge hospitality.

Meet Your Guide

Hey, I’m Winston, the founder and lead guide of Winston's Expeditions LLC. I grew up riding quads with my dad through the amazing ORV trails in pure Michigan. I joined the Marine Corps Infantry after high school. I moved back to Michigan and noticed my dad had a KTM dirt bike in the garage. The next thing I know, I bought a 2024 KTM 250 XCW 2 stroke and have been hooked ever since. I am working toward becoming a certified Michigan DNR ORV Volunteer Instructor. I handle the route navigation, cabin bookings, and grilling so you can focus entirely on the throttle.

My mission is simple: To take the stress, planning, and logistics out of Northern Michigan trail riding so you can just bring your bike and ride.