The Black Hills transform into a snowmobiler’s paradise every winter, offering miles of groomed trails, towering pines, and sweeping mountain views. Whether you’re a seasoned rider or brand new to the sport, Deadwood makes the perfect base for an unforgettable winter escape.
Day 1: Arrival in Deadwood + Warm-Up Ride
Morning
Settle into your Deadwood Connections Rental, and then grab lunch in town + pick up any last-minute essentials (gloves, hand warmers, snacks).
Afternoon
Warm-Up Trail: Custer Peak Access (Trail 7 – Northern Section).
A perfect introductory run with:
- Gorgeous views of the Black Hills forest
- Wide groomed paths
- Gentle elevation
Evening
Return to Deadwood for dinner (saloon-style or steakhouse – your choice!).
Relax by the fire, prep gear for tomorrow’s big ride.
Day 2: The Signature Black Hills Loop
Hit the trail early from the Dumont Trailhead.
Ride Trail 7 southbound, the backbone of the Black Hills snowmobile system.
Afternoon
Terry Peak Ridge Run
- High-elevation ridgelines
- Wide-open snowfields
- Panoramic winter view perfect for photos
LUNCH: Trailshead Lodge
- Refuel your machine & yourself
- Hot drinks + classic comfort food hit perfectly
Evening
Meadows & Forest Loop
(Trail 5 + 7A Connector)
- Rolling meadows
- Dense pine forests
- Peaceful, quiet stretches
- Connect to Trail 7A to return north toward Dumont, completing your loop
DINNER: Order in & enjoy hot tub soak
Day 3: Canyon Views + Leisure Ride
Morning
Spearfish Canyon Cruise (Trail 1)
- Start from Deadwood or Lead and hop onto Trail 1
- This ride features:
- Towering limestone cliffs
- Frozen waterfalls
- Narrow, dramatic canyon passages
- It’s one of the most scenic rides in South Dakota and perfect for photography
Late Morning
Depending on how you’re feeling:
- Continue extending into Spearfish Canyon
- OR make a shorter turnaround and enjoy a liad-back ride through side loops and spur trails
Lunch – Back in Deadwood
- Grab lunch downtown before packing up
Afternoon
Load up your snowmobiles, pick up souvenirs, and start the trip home – refreshed, exhilarated, and already planning next year!