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Show Up. Ride. We Handle the Rest.
At Winston’s Expeditions, we deliver elite, all-inclusive backcountry trail vacations for passionate riders. We host all-inclusive, 3-day/3-night dirt bike getaways in Kalkaska, MI. Limited to just 3 to 5 riders, we provide a premium trailside lodge, fully catered steak dinners, and expert-guided 100-mile loops—with zero Sunday checkout rush.
You bring your bike; we handle the lodging, food, routing, and trail safety.
The Ride: A curated 100-mile Saturday loop & 50-mile loop Sunday.
The Lodge: 3 full nights at a private cabin with front-door trail access.
The Menu: Friday welcome pizza, American breakfast, Saturday diner lunch, and ribeyes on the grill.
The Pace: Leave Sunday night or Monday morning. No Sunday checkout rush.
Small Group Atmosphere: Ride in tight-knit groups of like-minded adventurers. 3-5 riders per trip.
The Safety: Full backing by a Garmin inReach satellite lifeline and first aid kit.
Price: $1000 All-Inclusive. Secure your slot today with a $500 non-refundable deposit. The remaining $500 balance is due 14 days before your expedition kicks off.
All-Inclusive Michigan ORV Guided Trip
All-Inclusive Michigan ORV Guided Trip
What’s Included
What’s Included
Dates: June 4-7, 2027
Dates: June 4-7, 2027
Duration: 3 days, 3 nights
Duration: 3 days, 3 nights
Location: Kalkaska, Michigan
Location: Kalkaska, Michigan
Expert Guides & Currated routes: Local with knowledgeable trail experience
Expert Guides & Currated routes: Local with knowledgeable trail experience
Meals & Lodging: Included
Meals & Lodging: Included
Riders: 3-5 Riders only per trip
Price: $1000 All-Inclusive.
What’s Not Included
What’s Not Included
Bike: Not Included
Bike: Not Included
Protective Gear: Not Included
Protective Gear: Not Included
ORV permits: Not Included
ORV permits: Not Included
Itinerary Snapshot
Itinerary Snapshot
Day 1: Arrival, orientation, bike check
Day 2: Full-Day of riding
Day 3: Full-Day of riding
Day 4: Depart
Requirements
Requirements
A Valid Motorcycle Endorsed License
A Street legal Dual Sport Motorcycle / DirtBike with spark arrestor
ORV trail permits
Helmet/ Goggles/ Gloves/ Boots
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