The Pioneer Trail

Day 1: Calgary, Alberta

Nestled in the foothills of Canada’s Rocky Mountains, Calgary is a place where visitors come to explore the heritage of the Canadian West. Shopping and dining options abound. The city is also home to numerous parks and outdoor spaces.

After checking into your hotel, head out for dinner. For a good taste of Alberta, try Hayden Block in the Kensington District.

Day 2: Calgary, Alberta

Enjoy a leisurely day in Calgary, the largest city in Alberta.

Get outfitted for your upcoming adventure with a stop at Alberta Boot Company. Founded in Calgary in 1978, the Alberta Boot Company continues to craft each pair of their boots (the official boots of the Calgary Stampede) in their Canadian workshop.

You can take a tour to see how the legendary boots are made and try on a pair for yourself in beautiful showroom.

Day 3: Drumheller & the Canadian Badlands, Alberta

Today, you will be heading for the Drumheller Valley, the heart of the Alberta “Badlands.” Gouged from the prairie landscape by prehistoric wind, water and ice, the Badlands are as mysterious and moon-like today, as they were when they were formed. Exposed sedimentary rock reveals 70 million years of geological history within the layers. You may also wish to stop at Dinosaur Provincial Park later in the day.

Visit the Royal Tyrrell Museum of Palaeontology. Found in the heart of the valley along the North Dinosaur Trail, the museum lays out the story of the evolution of the earth and the golden age of the dinosaurs in an exciting and educational format guaranteed to keep you spellbound for hours.

End your day in Brooks, Alberta.

Day 4: Saskatoon, Saskatchewan

Depart Brooks and the Badlands for a journey across the vast Canadian prairie to Saskatoon, Saskatchewan’s largest city.

Saskatoon has a beautiful river valley to explore, as well as a delicious foodie scene. Read about the farm-to-table philosophy of Odla before visiting for dinner at this Saskatoon restaurant.

While in Saskatoon, stop for a visit at Remai Modern, a renowned gallery.

Day 5: Regina, Saskatchewan

Today, you will travel to Regina, Saskatchewan’s capital city. Along the way, you may wish to detour to Little Manitou Lake, famous for its high saline and mineral content (often referred to as the Dead Sea of the Prairies).

Regina is home to a 100-year-old symphony orchestra and arguably the nation’s most passionate sporting enthusiasts. From the serene park created at the heart of the city and the many exhilarating festivals to fascinating museums, galleries, heritage and science centres, Regina is a fascinating city to explore.

Day 6 - 8:  Ranch stay near Kyle, Saskatchewan

You will journey west today towards the small community of Kyle. Just outside of Kyle is La Reata Guest Ranch where you will stay for 3 nights. This will allow you two full days to live the ‘cowboy’ lifestyle and see the workings of an authentic operating cattle ranch. 

When we are not in the saddle, there are plenty of other activities to do. You can walk down to Lake Diefenbaker for swimming, boating, canoeing and waterskiing (on availability). The lake also offers a great opportunity for fishing. The large ranch property allows for wildlife viewing while hiking on the rolling hills, with deer, coyotes, foxes and owls, and overhead a Golden Eagle or a pair of Pelicans.

For some solitude, find a private spot along the 14km ranch shoreline with narrow but sandy beaches here and there. In the evening, do what the cowboys do: engage in a game of horseshoes, learn how to handle a Lariat or improve your skills by dummy steer roping. Or visit the La Reata Saloon, where there is a pool table, foosball and darts.

End the day with the crackle of a campfire and roast marshmallows as an evening snack. Listen to country music or sit in the hot tub under the stars. On some nights we can visit the nearby (22km) famous White Bear Saloon for some hot wings and drinks.

Day 9: Medicine Hat, Alberta

After your fun and relaxing ranch stay, continue westward back into the province of Alberta. This evening you will be staying in the Prairie town of Medicine Hat. Canada’s sunniest city is set in a lush river valley among wide-open prairie and red rock cliffs. Celebrate history, culture and spectacular nature at Medicine Hat’s history museums, cafes,art gallery and 100 parks and nature trails.

Stop in to see the Saamis Tepee (pictured above), billed as ' the world's tallest tepee'. Originally constructed for the Calgary 1988 Winter Olympics, each of the 10 masts feature a large storyboard depicting aspects of Indigenous culture and history. Just beyond the tepee is the Saamis Archaeological Site, which is one of the most important archeological sites in the region. Experts believe more than 83 million artifacts are buried there.

We also suggest you look at travelling the short distance south en route to Medicine Hat to visit Cypress Hills Interprovincial Park. The Cypress Hills rise 600 metres above the plains in southeastern Alberta where an ancient glacier hesitated and swerved.

Day 10: Pincher Creek, Alberta

Today travel via Lethbridge to Fort McLeod where you may wish to visit the North West Mounted Police Fort built in 1874. Just beyond Fort Macleod lies one of the most spectacular heritage sites in western Canada: Head-Smashed-in Buffalo Jump. Uncover 6,000 years of history at one of the oldest, largest and best-preserved jumps in the world. 

At this UNESCO World Heritage Site, you will learn about Indigenous history in Alberta and see demonstrations of First Nations culture through dancing and arts. 

Alternatively, travel south and visit the spectacular Writing-on-Stone Provincial Park, another UNESCO World Heritage Site. This provincial park protects the largest concentration of rock art on the plains. Explore this National Historic Site with an interpreter, lounge by the bubbling Milk River and hike the hoodoo trails.

Day 11: Waterton Lakes National Park, Alberta

Take a short drive to Waterton Lakes National Park, the smallest of Alberta’s Rocky Mountain Parks, but considered by many to be the hidden jewel in the crown. The charming town of Waterton is surrounded by incredible mountain and lake scenery.

Stroll through the town to shop, dine at the restaurants, visit the beach or hike the trails that start from the town site. You will want to visit the Prince of Wales Hotel – a National Historic Site – for afternoon tea and lots of opportunities to take amazing photographs.

Day 12: Kananaskis & Canmore, Alberta

Head north on the famed Cowboy Trail (Hwy 22) along the foothills of the Rocky Mountains. You may wish to visit the Bar U Ranch National Historic Site – a working ranch that once employed the notorious Sundance Kid. Take a horse-drawn wagon ride and tour the outbuildings in a place that stands in tribute to the ranching history of western Canada. 

Head west on Highway 40 with a beautiful scenic drive into Kananaskis country and along the eastern flanks of the Rocky Mountains. Watch for wildlife!

For a different perspective on these ancient mountains, we highly recommend booking a tour with an Indigenous guide.

Heather Black of Buffalo Stone Woman offers short and long hikes that explore the landscape through an Indigenous lens.

Day 13: Banff National Park, Alberta

Spend your day exploring Banff, one of the most beautiful towns and national parks in the world. The Sulphur Mountain Gondola provides stunning views of Banff town and the surrounding mountains. Highlights of the area include: Bow River Falls, Tunnel Mountain Drive with the wind-eroded hoodoos and Lake Minnewanka. 

A short drive along the Bow Valley brings you to Lake Louise with stunning views across the turquoise lake to the Victoria Glacier. Keep in mind that during the busy summer months, the parking lot at Lake Louise fills up very quickly so we highly recommend taking the available shuttle from the Lake Louise ski area. The shuttle is dependent on availability so reservations are recommeded.

Nearby Moraine Lake is a beautiful stop later in the day but you must take a shuttle, which also leaves from the Lake Louise ski area.

Day 14: Calgary, Alberta

Return to Calgary for the end of your journey.