2026 Black Hills Road Trip Adventure – July 20–26
There are motorcycle trips and then there are epic journeys. Join us and take part in a one-of-a-kind 7-day guided motorcycle trip to the legendary Black Hills of South Dakota, a region known for its winding mountain roads, dramatic granite formations, historic towns, Old West character, and some of the most memorable motorcycle roads in North America.
This carefully curated trip begins and ends in Moose Jaw, Saskatchewan, with four nights based out of legendary Deadwood, South Dakota. Instead of packing up and changing hotels every night, riders will have time to settle in, explore the Black Hills properly, and enjoy daily routes designed around great roads, scenic stops, historic towns, and regional attractions.
Planned exclusively for experienced riders, this trip features curvy mountain roads and dispersed periods of heavy technical riding conditions. The pace of the trip is intended for experienced but non-aggressive riding, with multiple guides dispersed throughout the group to support the flow, safety, and coordination of the ride. The goal is to enjoy the roads, scenery, stops, and group experience without turning the trip into a race or endurance contest.
The group departs from Moose Jaw at 8:00 AM on Monday, July 20, 2026, and returns to Moose Jaw at approximately 5:30 PM on Sunday, July 26, 2026.
Riders will spend July 21–25 based out of Deadwood, giving the group time to settle in and experience the Black Hills without packing up and changing hotels every night. Daily routes are planned around a mix of iconic motorcycle roads, scenic stops, regional landmarks, small towns, and evening opportunities once the bikes are parked.
Highlights
- Needles Highway – One of the most iconic motorcycle roads in the Black Hills, known for its granite spires, narrow tunnels, tight curves, and unforgettable scenery.
- Iron Mountain Road – A legendary riding road featuring pigtail bridges, sweeping curves, one-lane tunnels, and views toward Mount Rushmore.
- Spearfish Canyon – A beautiful canyon ride with limestone cliffs, forested curves, waterfalls, and some of the most enjoyable scenic riding in the Black Hills.
- Custer State Park & Wildlife Loop Road – Ride through one of South Dakota’s most famous parks, with open prairie, forested roads, scenic lakes, and the possibility of seeing bison and other wildlife.
- Vanocker Canyon – A favourite motorcycle route through the northern Black Hills, offering curves, elevation changes, and a rewarding ride between Sturgis, Nemo, and the surrounding area.
- Mount Rushmore – One of the most recognizable landmarks in the United States and a classic Black Hills stop.
- Crazy Horse Memorial – A monumental mountain carving and cultural site located in the heart of the Black Hills.
- Badlands National Park – A dramatic contrast to the forested Black Hills, with rugged formations, open prairie, sweeping views, and unforgettable scenery.
- Devils Tower – A striking natural landmark in nearby Wyoming and a worthwhile ride destination for those wanting a memorable side trip beyond the Black Hills.
- Sturgis, Hill City & Custer – Historic towns, motorcycle culture, local food, saloons, shops, and walkable stops that help give the trip its character.
- Deadwood’s Historic Streets and Saloons – With four nights based in Deadwood, riders will have time to park the bikes, walk the town, enjoy local restaurants and saloons, and take in the Old West atmosphere.
- Days of ’76 - Deadwood’s Days of ’76 celebration, adding rodeo-week energy, historic parades, Old West atmosphere, saloons, and live entertainment to the evenings after the bikes are parked.
*Rodeo tickets and optional attractions are not included, but riders may have opportunities to take in additional events depending on timing, interest, and availability. The 2026 Days of ’76 celebration is scheduled for July 19–25 in Deadwood.
What’s Included
- Hotel lodging with complimentary hotel breakfasts
- Route planning
- Printed and/or digital route package
- Guided group ride structure
- Multiple guides dispersed throughout the group
- Daily ride coordination
Accommodations & Room Options
We’ve secured comfortable lodging with motorcycle travel in mind, conveniently located for rest, meals, and fueling up. accommodation arrangements are based on your registration type and group size. Rooming is first-come, first-served, so early booking is recommended.
Riders may register for shared or private accommodations, depending on availability and registration type.
Private Rooms
🧍 Solo or Couple (Private Room) - $1,300 CAD
You’ll have a private room with two-queen beds, or 1 king/queen bed subject to availability. Ideal for those who prefer privacy and a quiet space to unwind.
👨👩👧👦 Small Group or Family - $1,300 CAD
Small groups of up to 4 can register together and share a room with two-queen beds. This is the most cost-effective option for close friends or families.
💵 Shared Rooms = Shared Cost
To keep this trip flexible and affordable, rider have the option of sharing a room. The cost of each room can be divided among its occupants.
🧍 Solo Rider (Shared Room) - $650 CAD
Riders who wish to reduce individual costs may choose to share a room with two-queen beds with another rider. Room sharing may be arranged by registering with someone you already plan to share with, or by contacting us to discuss available rooming options.
❗ Costs Not Included
- Fuel – Each rider is responsible for fueling their own bike.
- Food & Beverages – Meals, snacks, and drinks are not included. However, we’ll stop frequently at local diners, cafes, and breweries.
- Personal Expenses – Souvenirs, optional excursions, and personal items are at your discretion.
- Motorcycle maintenance or repairs
- Travel insurance
Rider Requirements & Preparation
Each rider is responsible for proper riding gear, required travel documents (valid passport & motorcycle license), insurance, and a roadworthy motorcycle with a fuel range of no less than 180 km.
rain gear, tool kit, emergency contact information, and travel insurance are highly recommended
Riders should have the ability to ride for extended periods of time, rest stops are typically no longer than 1.5hrs apart but total daily excursions can be up to a total of 6hrs.
💬 Booking & Registration
Space is limited and spots fill quickly!
When registering, you’ll be asked to:
- Indicate your preferred room type
- List any roommate/group preferences
- Provide motorcycle/plate information (allows for quick accomidation check-in)
- Acknowledge that you are responsible for your own fuel, meals, and travel documents