group of people sitting on snowmobiles in the snow

A Snowmobiler’s Dream Weekend in the Black Hills

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

Outdoor view of small town shops

Morning

Settle into your Deadwood Connections Rental, and then grab lunch in town + pick up any last-minute essentials (gloves, hand warmers, snacks).

Couple walking together down dirt trail with lush green grass and bright blue skies

Afternoon

 Warm-Up Trail: Custer Peak Access (Trail 7 – Northern Section). 



A perfect introductory run with:

  • Wide groomed paths
  • Gentle elevation
  • Gorgeous views of the Black Hills forest


Couple looking at each other enjoying a meal together in a restaurant booth

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

Gourmet boxed chocolates ready to be savored

Morning

Hit the trail early from the Dumont Trailhead.


Ride Trail 7 southbound, the backbone of the Black Hills snowmobile system.

Group of bison in a field, playing in the tall grass and kicking up dirt

Afternoon

Terry Peak Ridge Run

  • High-elevation ridgelines
  • Wide-open snowfields
  • Panoramic winter views perfect for photos


LUNCH: Trailshead Lodge

  • Refuel your machine & yourself.
  • Hot drinks + classic comfort food hit perfectly.


Group of lavender on a spa table surrounded by fresh fragrances

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

Field of wild flowers with trees in the background

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.


Gold blocks and coins stacked on tops of each other

Late Morning

Depending on how you’re feeling:

  • Continue extending into Spearfish Canyon
  • OR make a shorter turnaround and enjoy a laid-back ride through side loops and spur trails


Lunch – Back in Deadwood

  • Grab lunch downtown before packing up.


Busy small town with people walking around and old trees in the background

Afternoon

Load up your snowmobiles, pick up souvenirs, and start the trip home - refreshed, exhilarated, and already planning next year!