A Unique Saskatchewan Road Trip Itinerary in Cypress Hills

Looking for the perfect Saskatchewan road trip itinerary to explore the province’s stunning landscapes, rich history, and unique attractions with your family? 

So many people are driving across Canada to Western Canada to see the impressive Canadian Rockies and the West Coast. But sadly, many drive through Northern Ontario and the Prairies without barely making any stops.

This is a shame since there are some pretty scenic drives in Saskatchewan, especially in Southwestern Saskatchewan, that are worth a multi-day visit.

With my two boys, I had the opportunity to explore the Cypress Hills area in Southwestern Saskatchewan. Let me tell you, there are unique places to visit in Saskatchewan that will make you wonder why you didn’t visit before. It’s one of the most scenic drives in Saskatchewan.

This carefully curated 4-day itinerary takes you on a fun family road trip through the southwestern region of Saskatchewan, including:

• the breathtaking Cypress Hills Interprovincial Park, 
• the historic Fort Walsh, and 
• the world-renowned T-rex Discovery Centre in Eastend.

✍️ Cypress Hills Grassland Destination Area invited us for a summer family road trip in Southwestern Saskatchewan, and we’re sharing our detailed itinerary and the best things to do in the Cypress Hills area (and more) with you! Note that all opinions and words are our own.

How to Get to Cypress Hills Area & Road Map of Southern Saskatchewan

This road trip itinerary covers the southwest region of Saskatchewan, including Cypress Hills Interprovincial Park, Fort Walsh, the town of Eastend, and the Frenchman River Valley. The map highlights the key stops, starting from the Alberta/Saskatchewan border and looping back towards Maple Creek.

If you wish to extend your visit to Saskatchewan and explore more of the province, such as Grassland National Park, Gravelbourg, and Moose Jaw, make sure to check out this six-day itinerary filled with Saskatchewan’s hidden gems.

💡Fun Fact: The highest elevations in Saskatchewan are found in the Cypress Hills, peaking at 4,567 feet (1,392 meters) above sea level. This is higher in elevation than the town of Banff in the Canadian Rockies, which is 1383m (4,537 feet) above sea level.

How to Get to Cypress Hills from Calgary and Regina

• From Calgary to Cypress Hills

The driving distance from Calgary to Cypress Hills Interprovincial Park is less than 400 km, and it takes around 4.5 hours to reach it. The route typically goes through Highway 1 East towards Medicine Hat and then Highway 41 South towards the Cypress Hills area. 

💡 Note that some sections of the Cypress Hills Interprovincial Park have gravel roads that are impassible when wet. The drive down to Eastend also has a gravel road section.

• From Regina to Cypress Hills

The driving distance from Regina to Cypress Hills Interprovincial Park is around 260 km, and it takes approximately 3 hours to drive there. The route usually follows Highway 1 West towards Swift Current and then Highway 21 South towards the Cypress Hills area. 

📖 TL;DR? Here is a recap of our 4-day road trip through Southwestern Saskatchewan.

Day 1: Stop at Elkwater in Alberta. Visit the Reesor Viewpoint. Head to Reesor Lake. Arrive at the Historic Reesor Ranch where you can immerse yourself in the authentic western ranch experience. Settle into one of the cozy log cabins for an overnight stay.

Day 2: Go on the Conglomerate Cliffs hike. Drive to Fort Walsh National Historic Site. Drive to Cypress Hills Central Block and enjoy a variety of activities here. I recommend going directly to the Core Area.

Day 3: Explore Cypress Hills Interprovincial Park a new way: on a wagon ride tour. Make your way to Eastend, about an hour south of Cypress Hills. Start at the renowned T.rex Discovery Centre. Take a stroll through downtown Eastend.  Take an evening tour of the Wilkinson Memorial Observatory.  

Day 4: Wake up early and start driving toward Maple Creek. Visit Grotto Gardens. Park in downtown Maple Creek and start exploring.

Day 1: Drive to Historic Reesor Ranch in Cypress Hills Interprovincial Park

Begin your road trip in Saskatchewan by driving to the Historic Reesor Ranch in the West Block of Cypress Hills Interprovincial Park. 

Alberta Side of Cypress Hills Interprovincial Park

On your way to the resort, you can stop at Elkwater in Alberta. It’s a charming lakeside town with plenty of outdoor activities and stunning scenery. There is also a nice beach if you need to cool off.

Next, visit the Reesor Viewpoint. You’ll have breathtaking views of the Cypress Hills and the surrounding prairie landscape. Take a moment to soak in the panoramic views and snap some photos. I was surprised at how many wildflowers there were. 

Afterward, head to Reesor Lake. You can’t swim in that lake, but you can enjoy picnic tables and fishing docks.

After you pass Reesor Lake and drive toward Reesor Historic Resort, you’ll drive on a gravel road until you reach the resort. You might lose cell service for a little while. You’ll also cross over to Saskatchewan a little before arriving at the resort.

When you arrive at the Historic Reesor Ranch, you can immerse yourself in the authentic western ranch experience. It’s one of the not-to-miss Cypress Hills activities. You can go on a horseback riding adventure (opt for the 2-hour 4-PM adventure), or if your kids are still too little, you can book pony rides.

We did it during our visit. We booked a one-hour pony ride through a small obstacle course. The Wrangler was nice and took the time to show the kids how to prepare the horses for a ride. The kids got to brush the horses, put the saddle on and off, and, of course, give the horses some treats after the ride.

🛏️ WHERE TO STAY? Historic Reesor Ranch

At the end of the day, settle into one of the cozy log cabins for an overnight stay. Relax and unwind in the rustic charm of these accommodations, surrounded by the serene natural environment.

We had the Log Cabin, the one further away from the main cabin. It was a short drive or a 10-minute walk back to the main lodge (which is what we decided to do). It’s also where the hiking trail to the Conglomerate Cliffs starts.

We sadly didn’t go on the hiking trail because it was pretty hot when we visited, and the kids preferred to play some lawn games and enjoy the playground instead.

Below is a map of Cypress Hills, Saskatchewan, to help you better orient yourself:

Day 2: Fort Walsh & Cypress Hills Central Block

After a good night’s sleep at Reesor Historic Ranch, you can enjoy more of the property. You could go on the Conglomerate Cliffs hike or take the pony ride if you didn’t have time the previous day.

When you are ready to check out, you can drive to Fort Walsh National Historic Site. It’s only 27 km from Reesor Resort, but it’s on a gravel road, so plan for a good 40-minute drive.

Fort Walsh National Historic Site

Fort Walsh National Historic Site was an important place in the 1870s when the North West Mounted Police brought law to western Canada.

In the 1870s, there was a big fight called the Cypress Hills Massacre between the Nakoda people and some wolfers (people who hunted wolves for their fur). This fight was very important and had a big impact on the Nakoda people and all of Canada. The North West Mounted Police came to Fort Walsh to keep the peace and ensure everyone followed the law.

It was a busy and important place in Canada until the CPR built the railroad near Maple Creek.

Today, you can visit Fort Walsh National Historic Site in southwest Saskatchewan and return to the 1870s! It’s a fun things to do in Cypress Hills.

I recommend participating in one of the guided tours of the fort. They are about an hour long and super interesting. My oldest son LOVES to ask many questions.

After the tour, you can also walk to the Cypress Hill Massacre Site, but once again, it was too hot for the kids to walk that long, so we enjoyed the museum inside the visitor center instead…. 

Of course, we took pictures of the Parks’ Canada red chairs, like we did when we visited Waterton Lakes National Park.

💡 Note that you’ll have free access to Fort Walsh if you have a Parks Canada Discovery Pass. Make sure to bring the pass with you.

After exploring Fort Walsh, head to Cypress Hills Central Block.

Cypress Hills Central Block

Once again, the drive from Fort Walsh to Cypress Hills Central Block is on a gravel road with limited cell service. It takes about 45 minutes to get there.

You can enjoy a variety of activities here. I recommend going directly to the Core Area and parking there. You can then visit the Visitor Center, the small museum, and see the park’s summer activities.

During our visit, the kids participated in a few learning activities from the EYES program (Educating Youth in Engineering and Science) that promotes STEM subjects.

The kids got to do some robot coding activities and learn how the Northern Lights work and how to create a star. It was a lot of fun.

Then, you can enjoy the public pool and simply walk around the area. We grabbed a quick dinner at the Lakeview Grill and had ice cream for dessert.

If you still have some energy, you can stop for a round of mini-golf at the Lone Pine Pizza and Mini-Golf.

🛏️ WHERE TO STAY? Cypress Hills, Saskatchewan Camping Options

For our visit to Cypres Hills Interprovincial Park, we booked a campsite at the Warlodge Campground, one of the six campgrounds in the Central Block.  I booked the campsite #52, and it was PERFECT.

It was conveniently located next to a playground, which was amazing for keeping the little ones entertained. 

💡 Note: Cypress Hills is also one of Canada’s largest Dark Sky Preserves, along with Jasper National Park. The park has an observatory and offers a night stargazing tour. We did not participate because the kids were exhausted, but if your kids are a bit older, I highly recommend booking a visit to the Cypress Hills Observatory.

Day 3: Wagon Ride, T-Rex Discovery Centre

On your third day of road-tripping through Saskatchewan, start your day slow at the campground. I enjoyed my French press coffee while the kids were playing with some new friends at the playground.

Cypress Hills Segway Tours

When ready, you can explore Cypress Hills Interprovincial Park a new way: on a wagon ride tour with Cypress Hills Segway Tours. This is a fun way to see the park.

Ask for the kids’ scavenger hunt so they stay engaged for the entire hour. It was amazing to see so many wildflowers.

Next, it’s time to leave Cypress Hills Interprovincial Park and explore more of Southern Saskatchewan. Make your way to Eastend, about an hour south of Cypress Hills. 

💡 Note that you’ll be driving on a gravel road for most of the drive.

Start at the renowned T.rex Discovery Centre.

T. Rex Discovery Center

T-Rex Discovery Center in Eastend, SK, is a cool place to visit. When we drove across Canada the first time, we stopped at the Royal Saskatchewan Museum in Regina and saw Scotty the T-Rex, the world’s largest T. rex!

But we never realized it was discovered in Eastend. The T. rex fossil was discovered in 1991 by a family near Eastend. Scientists later realized it was one of the largest and most complete T. rex skeletons ever found! The fossil is about 65 million years old, from the late Cretaceous period.

In addition to the massive T. rex skeleton, the museum has many other cool dinosaur fossils and exhibits. You can see fossil specimens, learn about paleontology, and even go to a dinosaur dig pit where kids can use tools to uncover real dinosaur bones and fossils buried in the sand.

This was my son’s favorite part of the museum. This and also the scavenger hunt.

 It’s a super fascinating place for dinosaur lovers of all ages!

They also have an outdoor self-guided tour trail around the museum, where you can admire the Badlands landscape. There is also an outdoor kids’ play area with dinosaur toys and games.

Plan for at least 2 hours at the T. Rex Discovery Center, maybe even a little more if you want to complete the entire hike.

After your dinosaur adventure, take a stroll through downtown Eastend. 

Downtown Eastend

First, grab an iced coffee and ice cream at The Kilted Kitchen just off the main street. This local shop is in a house, so it might feel like you are not in the right place. But I assure you, the GPS will bring you to the right place where you can enjoy a good coffee and fun ice cream.

They also serve donuts (that looked delicious, but the kids opted for ice cream instead).

Then, you can continue walking and visit the Eastend Historical Museum to delve deeper into the area’s rich history. The museum promotes the history of Southwest Saskatchewan. Plus, you can also see Corky Jones, one of Eastend’s earliest settlers, who has a collection of locally discovered fossils and dinosaur bones.

Outside, you can walk inside a few different log houses that have been refurbished with artifacts from that period. The kids loved the scavenger hunt and searching through the museum and its different buildings.

The admission fee is per donation.

The Eastend Historical Museum also serves as a Tourist Information Centre, so don’t hesitate to ask them for information on other things to do in the area.

🛏️ WHERE TO STAY? Eastend Campground

When you are ready, head to the Eastend Campground where you’ll spend the night.

When we visited, it was during the Dino Days festivities, so we stayed at the campground to participate in the different activities. But if you’re visiting another time, you can also walk to the public outdoor pool. There is a big slide. The kids will love it.

BONUS: Wilkinson Memorial Observatory

If your kids are still up and have more energy, I highly recommend a tour of the Wilkinson Memorial Observatory.  

The Cypress Hill and Grasslands area offers amazing opportunities for stargazing since there is not much light pollution.

Just outside the town of Eastend is the Wilkinson Memorial Observatory, which offers guided tours at night. The admission fee is per donation.

The tours start at 9h30PM (on clear summer evenings), where you can look at the sky through their Celestron Ultima 11” 2800mm focal length telescope.

We loved learning about the sky and the different constellations and looking through the telescope. But sadly, the kids were getting pretty tired, so we didn’t stay the entire time.

We’ll have to come back when the kids are a bit older.

Day 4: Grotto Gardens & Downtown Maple Creek

Wake up early and start driving toward Maple Creek. There is not much on the way to Maple Creek, so you can drive directly to Grotto Gardens.

Grotto Gardens

The kids will LOVE Grotto Gardens Family Fun Farm. There is so much to do at the farm, including:

• Petting zoo
• Mini-golf
• Train ride
• Alpaca walk,
• …

I suggest you start with the farm train ride. It costs $9.00 per adult and $8.00 per child for a 30-ish-minute train ride around the farm. During our tour, we made a few different stops.

The first one was in the Saskatoon berry orchard, where we got to pick (and eat) a few berries. It was only our second time tasting Saskatoon berries; the first time was at DNA Garden near Lacombe in Central Alberta.

Then, we stopped to see (and feed) the goats and cheeps. We also saw the donkeys. We ended the tour with the alpacas.

It was a great way to see the farm and the different animals. Then, we continued our self-guided visit and fed more animals before treating ourselves with a local treat. 

After a few hours at the farm, drive to downtown Maple Creek.

Downtown Maple Creek

Park in downtown Maple Creek and start exploring with a visit at Jasper Cultural & Historical Center.

Jasper Cultural & Historical Center is an old school building from 1910. It used to be called the Jasper Street School. Hundreds of kids went there to learn until 1986. 

Today, Jasper Center has rooms with different themes inside. These rooms show off historical artifacts from the area. There is also a photography exhibition on the life of the Cypress Hutterite Colony.

Once again, my boys completed the little scavenger hunt (don’t forget to ask for it!).

When you’re done, you can walk around downtown Maple Creek and stop at the Old Timers Museum.

Then, walk to the Old Timers Museum.

The Old Timers Museum in Maple Creek is about the frontier days. It was started in 1926 to help people remember what life was like in the Cypress Hills area.

The museum is located in a 1935 log building, possibly the oldest museum building in Saskatchewan. 

This museum lets you see old things from the frontier, over 100 years ago, in western Canada. You can also learn how tough life was for the settlers and Native people who lived on the prairies then. Plus, there are many animal specimens.

🛏️ WHERE TO STAY? Willowbend Campground

After a long and busy day, it’s time to relax at Willowbend Campground, a few blocks from Maple Creek’s main street. It’s a nice campground with lots of trees.

Here are a few tips for your Saskatchewan Road Trip

– Pack snacks and drinks to avoid frequent stops, especially in remote areas. Saskatchewan has vast stretches of open roads, so it’s wise to have provisions on hand.

– Download offline maps or carry a physical map, as cellular service can be spotty in some areas.

– Plan your stops, taking into account the distances between attractions and the needs of your family members.

– Carry a basic emergency kit, including a first-aid kit, jumper cables, and a spare tire.

– Check road conditions and weather forecasts before setting out, as Saskatchewan’s climate can be unpredictable, and some roads on this itinerary are inaccessible.

Bring some cash. Some local museums, such as the Eastend Historic Museum and the Old Timers Museum, accept payment by donation in cash only.

Final Thoughts: Southwest Saskatchewan Road Trip Itinerary

Saskatchewan is so much more than blue skies and prairie lands. This road trip through Southwest Saskatchewan will lead you through the hills of Cypress and the historic Fort Walsh, the Canadian Badlands, where you can see the largest iconic Tyrannosaurus rex skeleton and even experience the dark, starry skies of Saskatchewan.

It’s one of the most scenic drives in Saskatchewan.