Overview
Day 1: Hitting the Road – Early Mornings
Today started way earlier than usual—5:00am, to be exact. There’s something about the anticipation of a road trip that makes it impossible to sleep in. We were up, buzzing with excitement, getting ready to hit the road. Packing the car always takes longer than expected, but there’s a certain satisfaction in seeing everything fit just right. This time, we are driving a rented Kia Sportage SUV. It claims to get more than 30 miles to the gallon, so we are curious to see if it lives up to the hype. We anticipate the trip will be around 10,000 miles and since we got a great deal on a rental car, we decided to NOT put all those miles on our own vehicle – and should save some money with better gas mileage than our own vehicles.
Before heading out, there was one minor pit stop in Purcellville. Apparently, you need a special insurance card to take a rental car into Canada—who knew? So, we planned to leave around 8:40am, swing through Purcellville to grab the card from our automobile insurance company, and then officially start the journey.
Washington Pennsylvania
Our first stop was Washington, Pennsylvania, for lunch with Nancy Bryant (a work colleague). Road trips are always better when you have good food and good friends waiting along the way. Nancy B is still working (from home) but managed to arrange her schedule to get an extended lunch hour. We meet at Tonya’s Tavern, the closest restaurant to her house.
Brandywine Falls: Cuyahoga Valley National Park
We have time before we arrive at our stop for the night to see a little bit of Cuyahoga Valley National Park. We pull into the first area we can find in the park and look at the map and decide we have time to go visit Brandywine Falls. The site was once part of a 19th century mill and there are still some traces of the old mill at the top of the waterfall.
Kent Ohio
Our first overnight stop of the trip is Kent Ohio where we meet a couple of our former colleagues, Laurel and Mike Stiller. Mike absolutely crushed it on the grill with roasted pork. We spent hours on the porch, swapping stories and reminiscing, then moved inside for more laughs around the dinner table. Nights like this remind me how important it is to slow down and enjoy the company of people who matter. We finally crashed around 11:00pm, full and happy.
Day 2: Trails & Old Friends — A Day on the Road
The morning started slow and sweet—Mike whipped up a fantastic little breakfast casserole that was basically French toast in disguise. It was warm, cinnamon-y, and comforting. We lingered over coffee and conversation until it was time for them to start their work day and for us to get back on the road. Honestly, even the morning chatter felt like a gift.
Back to Cuyahoga Valley
As we rolled out of Kent, we realized we had a few hours to spare—so why not dip back into Cuyahoga Valley National Park for another look? We pulled into the visitor center, but it was still early and not open yet. No matter. We wandered around, snapped a few photos, and then headed out along the Towpath Trail, tracing the old Ohio & Erie Canal. There’s something grounding about walking where history once flowed—quiet, leafy, and full of stories.
Lunch with Lois
Back on the road, we made a pit stop in Sylvania Ohio at Roosters, a laid-back sports bar where Nancy met up with her childhood friend Lois Froehlich Sanders. They hadn’t seen each other in forty-five years—can you imagine? Lois was working, so we only had about an hour and a half, but it was enough for hugs, laughs, and a few “remember when” moments. Roosters turned out to be a great little spot for catching up.
Lake Orion Evening
Our final stop for the day was Lake Orion Michigan to visit our longtime friend and former Colleague Carol Eldridge. Oh my gosh, what a joy! We dove headfirst into memories from our Datatel days—names, stories, and all the quirks that made that chapter unforgettable. Carol cooked up a delicious beef stroganoff, and after dinner we settled onto her back deck, overlooking the lake. The water was calm, the air soft, and the conversation flowed like it always does with old friends—easy, deep, and full of laughter.
It’s days like this that remind us how rich life is when you mix good food, beautiful places, and the kind of friendships that span decades.
Day 3: From Lake Orion to Lake Michigan — A Day of Friends, Food & Small-Town Charm
Harrison kicked off the morning with a quiet walk around Lake Orion, soaking in the neighborhood where Carol lives. There’s something grounding about seeing a place before the day really begins—birds chirping, lake mist rising, and the streets still sleepy. After a bit of exploring, he headed back to pack up and hit the road for our first stop: Kalamazoo.
Kalamazoo Catch-Ups
This leg of our Michigan journey was all about reconnecting. We met up with longtime friends—Tom, Dawn, and Tracy—who call this part of the state home. We’d recently seen Tom and Dawn at our home, but none-the-less, we enjoyed time together at Cove Lakeside Bistro for lunch, laughter and stories. Afterward we swung by Bell’s Eclectic Cafe to meet Tracy for a drink and more reminiscing. It’s amazing how quickly time melts away when you’re with people who’ve shared your past. By late afternoon, we said our goodbyes and pointed the car toward Manistee.
Manistee Magic
Arriving in Manistee, we were greeted by the charm of a lakeside town which feels like it belongs in a storybook. Nestled on the Lake Michigan shore, it’s full of character—historic buildings, three harbors, and a downtown riverwalk that invites you to slow down and take it all in.
Ramsdell Inn
We checked into the Ramsdell Inn, a beautifully restored Victorian building right in the heart of downtown. It’s steps from the riverwalk, shops, and restaurants, and it instantly felt like the perfect home base for the night. The Inn occupies the upper 2 floors and the main floor is home to TJ’s Pub. We stop in the pub and it’s smaller than it looked and was packed with what appeared to be locals enjoying happy hour. Before the sun dipped below the horizon, we wandered the streets and walked part of the riverwalk, letting the town’s quiet elegance sink in.
American Legion Stop
As is tradition, we popped into the local American Legion to check it out. This one doesn’t serve food, but it’s always worth a visit for a beer or two. The vibe was friendly and relaxed. We chatted with a few locals over a couple of beers, then headed out in search of dinner.
Pizza by the River
We landed at Fricano’s, a cozy pizza spot right on the river. The pizza was fantastic—crispy, cheesy, and generous enough to leave us with leftovers for tomorrow’s lunch. With full bellies and happy hearts, we made our way back to the inn for a good night’s sleep. Tomorrow promises more adventure, and we’re ready for it.
Some days are about movement, others about connection. This one had both—and a little lakeside magic to top it off.
Day 4: From Lake Michigan to Haviland Bay Ontario — A Day of Shorelines, Stories & Sunsets
Harrison woke up at daybreak and went for another solo walk, drawn outside by the stillness of the morning and the promise of one last look at Manistee before we hit the road. The sky was clear, the air crisp, and the town was just beginning to stir. He wandered into a part of town we hadn’t explored the night before, pausing on a bridge to watch early-bird fishermen casting lines into the quiet water. There’s something meditative about watching a town wake up.
Back at the hotel, we packed up and hit the road. With no breakfast at the inn, we opted for a quick stop at Burger King—fast, easy, and just enough fuel to get us going.
Hugging the Michigan Shoreline
Our route took us west along the Lake Michigan shoreline, with a stop at Point Betsie Lighthouse. We didn’t go inside (we arrived just before it opened), but the views from the shoreline were stunning—waves lapping against the rocks, the lighthouse standing tall against the blue sky. A few photos later, we were back on the road.
Sleeping Bear Dunes Overlook
We’ve been to Sleeping Bear Dunes National Lakeshore before, but it was worth a return visit. We hiked the dune for a bit, took in the sweeping views of the lake waters, and then made our way to Glen Haven, a preserved historic village with a blacksmith shop, an old cannery, and a hotel dating back to 1857. It’s like stepping into a time capsule—quiet, weathered, and full of stories.
Roadside Snacks & Small-Town Sights
From there, we cruised through a series of delightful quaint towns we’ve visited before: Traverse City, Elk Rapids, and Charlevoix. We stopped at a roadside park for a snack break—Pringles, peanut butter and crackers on a picnic bench. The park had an unexpected backstory: it was once the site of a nuclear plant that was later relocated. Just one of those quirky roadside facts that makes you pause.
Crossing the Mighty Mac and the International Bridge
By late afternoon, we approached the Mackinac Bridge that connects lower Michigan with the Upper Peninsula of Michigan. Nancy wasn’t keen on driving across, so Harrison took the wheel. The span never fails to impress—five miles of steel and sky linking Michigan’s two peninsulas. Another 45 minutes up the road, we stopped for gas in Sault Ste. Marie, then crossed the International Bridge into Canada. A quick toll, a smooth customs check, and just like that, we were in Ontario.
Welcome to Haviland Bay
Our final stop for the night was Macauley’s Hotel in Haviland Bay. A quick phone call confirmed our keys were already in the room, and we were greeted by Chris, the owner’s son. His parents, who recently moved from Niagara Falls to take over the place, were warm and welcoming. While the hotel & restaurant have been around since 1938, they’ve only been running it for five months and it already feels like a cozy lakeside retreat. While the place doesn’t look like much, we can tell they’ve put some time & energy into making improvements; it a delightful and quite memorable place.
We had dinner at their on-site restaurant. In our “pre-search”, we knew this stretch of the road had little to offer and it was either eat here or drive 20 minutes back in the opposite direction. Dinner was classic and hearty—fish and chips with portions so big they could’ve fed a small village (or at least two hungry travelers). We shared a couple of beers and some great conversation with the owners, who suggested we catch the sunset down at the beach.
So we did.
We grabbed a couple more beers from our cooler and followed a dirt path to the lake. The evening was warm, the sky painted in golds and pinks, and the water calm. It was one of those moments that makes you stop and breathe it all in.
From sleepy towns and historic lighthouses to border crossings and beach sunsets—today was a full chapter in this road trip story. And we’re just getting started.
Day 5: Granola Bars, Lake Views & Thunder Bay Tales — A Day on the Trans-Canada Highway
We rolled out of bed around 6:30am this morning—still dark outside, but the coffee helped kick things into gear. After a quick shower and a couple of granola bars (breakfast options were nonexistent in this neck of the woods), we packed up and hit the road by 8:00am.
Scenic Drive to Thunder Bay
The first stretch westward on the Trans-Canada Highway is beautiful. Lake Superior peeked through the trees at every overlook, and traffic was practically nonexistent—just the occasional car or truck behind us. We passed through four or five construction stops, each only a couple minutes long so they barely slowed us down. Then, it was miles of forest, the occasional waterfall, and fog drifting through the trees. As we got closer to Thunder Bay, the landscape opened up again with some truly breathtaking views.
A Trailhead, a Park, and a Surprise
We stop at a few overlooks for pictures but when we get back on the road and that’s when our oil light came on. Not just a light, but somewhat stern wording across the dashboard indicating the oil needed to be changed. Luckily, we had cell phone service, so we called the car rental‘s national number. They gave us a reference number and told us to go ahead and get an oil change and they would reimburse us when we turned in the vehicle. The gas station was attached to an A&W and given what we passed (or didn’t pass, actually) in the last 3 hours, we figured it was our best shot for lunch. It turned out to be a solid burger, and of course, we had to get a root beer.
Thunder Bay & the Oil Change Saga
We rolled into Thunder Bay around 4:30pm and immediately looked for one of those quick oil change locations. Luck was on our side—just half a mile from our hotel, we found one. A short wait behind a couple of cars, and we were out in 20 minutes. Nancy said it cost about $90 USD, which felt steep, but hey, the cart rental company would cover it.
Courthouse Hotel & Check-In Chaos
Our hotel was a converted old courthouse, which sounded cool—until we hit the check-in line. Only six people ahead of us, but two elderly couples were deep in a debate over senior discounts. The clerk kept explaining that since they’d pre-paid via booking.com the hotel could not offer money back for a senior discount, but they weren’t having it. Then the next couple was meeting someone else there and wanted to switch rooms to be closer. Twenty minutes of standing in line until we finally got our room. Our check-in took us all of three minutes. Go figure.
Wings & Netflix
When we travel, we do research to make sure our hotel choice will be within walking distance of several choices. Tonight, we want to watch sports, so we head out for dinner at On Deck, a sports bar just down the street. Big place, lots of pool tables and TVs. We grabbed a couple of beers and were pleasantly surprised when they brought out a sampler basket—a few wings and mini pizza slices. So good, we ordered a full batch of wings with the same flavor. We hung out for a couple hours, caught a Friday night college football game, and watched the Toronto Blue Jays play-off game.
The night ended back at the Courthouse Hotel with Netflix and a Pierce Brosnan/Helen Mirren flick called The Murder Club. We made it halfway through before sleep won out—guess we’ll catch the rest tomorrow.
From foggy overlooks and roadside burgers to courthouse hotels and surprise samplers, today was a mix of scenic beauty and quirky moments. Tomorrow, adventure calls again.
Day 6: Forts and Football — A Full Day in Thunder Bay
After a few restless nights on the road, we both finally got a solid sleep—woke up around 6:45am feeling like a humans again. Harrison made some of coffee in the room, we stretched a bit, and by 8:00am we were dressed and heading down to the hotel’s breakfast nook. Nothing fancy, but it did the job.
Nancy wanted to catch up on bills, so she set up the tablet while Harrison headed out to explore Thunder Bay. In case you haven’t picked up on this, Harrison LOVES early morning walks to get in 6-8 miles and explore the area as it comes alive for the day. The town’s waterfront is surprisingly lovely—little parks, a big marina, and walking paths hugging the shoreline. There was a fitness run happening, so the streets were blocked off and joggers were everywhere. He wandered through side streets, soaking in the vibe. Thunder Bay’s got a bit of everything—some areas clearly revitalized, others still showing wear. But overall, it leans more charming than sketchy.
Fort William Historical Park
Around 10:00am, we drove 20 minutes to Fort William Historical Park, a massive reconstructed fur trading post. The visitor center was buzzing—turns out a wedding was being set up, so we got to watch guests trickle in. From there, it was a mile walk to the tour starting point, a rustic shelter with a smoky fire and two guys deep in character, dressed in period garb. One woman immediately complained about the smoke (asthma), and the group took its time gathering. The tour kicked off slowly—really slowly—and set the pace for the entire tour. Eventually, we were led to a First Nations woman demonstrating wigwam repairs with birch bark. Fascinating, but the pace was glacial.
Then came the main fort—far bigger than we expected. It’s less a military fort and more a sprawling trading complex. We visited the canoe workshop, where they were building traditional birchbark canoes. Apparently, they only lasted about three years, and each canoe carried six 90-pound fur packs. That’s 540 pounds per person, portaged in stages. Brutal.
The guide was thorough but painfully slow, repeating answers multiple times because tour participants weren’t listening, so the same questions were asked multiple times. We think the worst were question and answers about how they made pitch (pine resin, charcoal, bear fat… heard it five times). The crowd was older so perhaps they just weren’t catching the details the first (and second, and third) time around.
Our guide mentioned that a movie was being filmed on-site, which explained why some areas were roped off. With the grueling slow pace, Harrison wandered off anyway, snapping photos of the blacksmith shop and other buildings. Eventually, we regrouped at the fur packing warehouse—tons of beaver, fox, bear, deer, and caribou pelts stacked like history in motion. The next stop was the trading post store and the apothecary, both filled with period items—gunpowder, cloth, medicine. The final stop was a grand hall currently set up for filming the movie, complete with candlelit tables and antique furniture.
By the time we walked back, the wedding was in full swing—guests arriving, music starting, and the whole place buzzing with energy.
Football & Food at On Deck
On the way back, we stopped at a scenic overlook to bask in the view and snap a few photos, then returned to the hotel and walked to town for dinner. While we rarely go to the same restaurant twice, we had poked our heads into other restaurants the previous evening and nothing else felt like the right vibe. We really enjoyed the food last night and had struggled to make our selections, so we just made today’s decision simple and returned to On Deck, the local sports bar. We parked ourselves there for the next four hours, watching some epic college football. West Virginia vs. Pitt went into overtime, and Georgia vs. Tennessee was another nail-biter.
We were so settled in, we ended up eating two meals—a late lunch around 2:00 (we were starving), and later, a pizza we planned to take with us for the next leg of the trip. Tomorrow’s drive to Winnipeg was going to be a long one—probably 7 to 9 hours—so today was all about recharging. On a 42-day road trip – sometimes you just lay low and mostly recharge.
The Never-Ending Movie
Back at the room, we tried to finish Thursday Night Murder Club with Pierce Brosnan & Helen Mirren. Second time’s the charm? Maybe. But we both fell asleep halfway through—again. One of these nights, we’ll actually see how the movie ends.
Thunder Bay gave us a full day—history, scenery, football, and a few laughs. Tomorrow, the road calls again. Winnipeg, here we come.
Day 7: Giant Mosquitoes, Moose, and Manitoba — Roadside Wonder Rolling into Winnipeg
We hit the road early today, continuing west on the Trans-Canada Highway, ready to push west toward Winnipeg. The drive was long and remote, with vast stretches of forest and lakes, but the scenery is great. Canada’s wilderness has a way of making even the emptiest roads feel full.
Roadside Oddities & Pizza Wins
Nancy had stumbled on this website called: makemydrivefun.com that points out quirky roadside attractions along (or near) your route and today we started exercising it. Our first mission was to find the legendary roadside statue of a giant mosquito carrying away a man in Upsala, Ontario. Yes, it exists—and yes, it’s every bit as ridiculous and delightful as it sounds. Along the way, we also passed by more quirky roadside attractions:
- Max the Moose (where we stopped and snacked on leftover pizza from last night—cold, delicious, and road-trip perfect)
- The Hitchhiking Sasquatch
- A Sheep Statue (at the Egli Sheep Farm and Animal Park entrance)
- The Center of Canada marker
- A Giant Coke Can
- And a sign marking Continental Divide, the point where all rivers begin to flow north to the Arctic
It’s the kind of drive where the journey really is the destination.
Welcome to Winnipeg
We rolled into Winnipeg around 4:30 and checked into Humphrey’s Inn & Suites.
After settling in, we headed out to explore downtown. The first sports bar looked promising from the outside—big and flashy—turned out to be tucked into the side of a casino and wasn’t even showing the game. So we wandered for several blocks and finally found Brown’s Social House, a regional chain.
The food was excellent, although a little on the pricey side, but worth it. The atmosphere was relaxed, slightly upscale, and just what we needed after a long day on the road. After dinner, we strolled back to the hotel and wound down with a little TV before calling it a night – finally finishing that movie!
A Note on Winnipeg
One thing we noticed while walking around Winnipeg—especially near the casinos—was the presence of quite a few homeless individuals. We had brief interactions with a couple of folks, and while it was sobering to see, there was no trouble. Just a reminder of the complex layers that make up any city.
Tomorrow, we’ll hang out in Winnipeg a bit longer before continuing west. So far, the weather’s been kind, the pizza’s been clutch, and the roadside oddities have been top-tier. Canada’s got character—and we’re soaking it all in.
Day 8: Parks, Pints & Pleasant Surprises — A Day in Winnipeg
We kicked off the morning around 6:30am, heading down to the hotel lobby for a classic continental breakfast—English muffins, bagels, Canadian bacon, scrambled eggs, and a little yogurt for Nancy. Nothing fancy, but it hit the spot.
After breakfast, Nancy stayed back to do a bit of research for the day while Harrison ventured out for a walk to get in his steps. The forecast hinted at rain around lunchtime, so he figured he’d make the most of the morning.
Exploring The Forks & French Quarter
Harrison wandered through The Forks, a sprawling park area right along the river and close to downtown. It’s home to the impressive Canadian Museum for Human Rights, which towers over the landscape with striking architecture. The park itself is peaceful and beautifully maintained. Crossing the pedestrian bridge, he found himself in Winnipeg’s French Quarter, home to a Catholic university and more riverside green space. There’s even a historic fort reconstruction nearby—though it looked more like an event venue than a tourist site. Still, it added a nice touch of history to the walk.
After soaking in the scenery, Harrison headed back to grab Nancy so we could explore the Exchange District together.
From Quiet Streets to Blueberry Ale
We strolled through the Exchange District for a bit, but it was quieter than expected—several restaurants and bars were closed, quite common for a Monday. The Exchange District’s name originates from the Winnipeg Grain Exchange, the former center of the grain industry in Canada, as well as other commodity exchanges that developed in Winnipeg between 1881–1918. By 1911, Winnipeg had become the third largest city in Canada and had more than two dozen rail lines converging near the city center. The Exchange District comprises twenty city blocks and includes approximately 150 heritage buildings.
Not finding any open restaurants, we pivoted and headed toward the waterfront, where Harrison had spotted a pizza place earlier on his morning walk. On the way, we stumbled upon a gem: The James Avenue Pumphouse Brewery. This place was a treat. The original 1906 pumping equipment was still on display inside the bar, giving it a unique industrial charm. The chef at this place (yes, a chef) prided his menu choices on signature dishes from several countries around the world (Greece, Thailand, Chile, India, Germany and Japan to name a few). On recommendation from our bartender, we enjoyed a mouth-watering appetizer and a superb entree. We settled in for a couple of hours, sipping on blueberry ale and soaking up the atmosphere. We HIGHLY recommend this establishment!
Evening at Bougee
After a short break back at the hotel, we headed out again for dinner at a cozy spot called Bougee Restaurant & Bar, a casual fine dining place. The door was locked when we arrived (5 minutes past the posted open time), but the grill chef (Chloe) came out and welcomed us in—already a good sign. We had a lovely evening chatting with her and enjoyed a simple but satisfying meal: a spinach dip with warm bread and an eclectic gourmet pizza that was absolutely unique delicious. Before leaving, we snapped a photo of her to remember the night.
Back at the hotel, we flipped on the TV and promptly crashed—another full day in Winnipeg, wrapped up with good food, good company, and a little local flavor. All in all, Winnipeg didn’t wow us like other places had so far. We’re glad we experienced it, but if traveling this way again, we would just make it a quick overnight stop. Maybe we missed something?
Day 9: Tractors, Prairie Skies & Fried Feasts — Rolling into Moose Jaw
We were up around 6:00am this morning, still adjusting to the time zone changes—showered, dressed, and down to the hotel lobby for breakfast. The hotel had the usual continental spread: bagels, bacon, hash browns, and plenty of coffee to get us moving. The skies were partly cloudy, but the temps were in the low 70s—perfect road trip weather.
Westward Bound on the Trans-Canada & The Manitoba Agricultural Museum
Getting out of Winnipeg took longer than expected. The city seems to stretch endlessly with suburban sprawl and strip malls. About an hour into the drive, we started looking for something to break up the monotony, and Nancy found the Manitoba Agricultural Museum (thanks to that new “make my drive fun” website). Off we went.
When we pulled up, it didn’t seem like the place was open – no vehicles in the gravel parking lot and no people in sight. We could see the place was like a fairground meets time capsule—massive covered buildings as far as the eye could see, packed with tractors and farm machinery from every era. We just started walking around when one of the workers showed us the not-so-obvious ticket building – so we headed there. We chatted with the woman at the ticket counter (great conversation), then spent a several hours exploring – yes, a several of hours. From horse-drawn equipment to steam engines, gasoline, and diesel tractors, it was the biggest collection Harrison has ever seen.
The museum also had a pioneer village tucked in the back with buildings like a barbershop, mill, and print shop, all filled with tools from the 1800’s. It was a fantastic stop we highly recommend.
Across the Saskatchewan Prairie
Afterward, we grabbed a quick lunch at a Subway nearby and continued west, watching the Saskatchewan prairie unfold in wide, golden waves.
Moose Jaw Arrival & Dive Bar Surprise
We pulled into Moose Jaw and checked into the Grant Hall Hotel a historic hotel first opened in 1927 that holds a significant place in Moose Jaw history. The guy at the front desk was dressed to the nines and really wanted us to try the upscale fine-dining hotel restaurant. He even walked us to the elevator. But we had other plans.
A short walk down the street led us to Rosie’s on the River, a spot Nancy swore was a dive bar. Turns out, it was a total gem. The walls were covered in 8-track tapes, the vibe was funky, and yes—there were a couple of heavily tattooed servers who added to the charm. We sat indoors but many folks were enjoying the unseasonably warm weather enjoying drinks and food on the outdoor patio – sat inside because every outside table was occupied. We ordered their sampler platter, which turned out to be a mountain of fried beef, fried chicken, and bacon wrapped tater-tops and french-fried potatoes. Harrison tried a few different beers while Nancy tried both the white sangria and the red sangria. It was delicious and absurdly indulgent—our arteries were definitely protesting. But we sat there happily, sipping drinks and soaking in the scene.
After dinner, we waddled back to the hotel and crashed almost immediately. A full day of prairie roads, vintage tractors, and deep-fried everything will do that to you.
Tomorrow, we’ll see what Moose Jaw has to offer in the daylight. But for now, we’re calling it a night—full, happy, and a little greasy.
Day 10: Tunnels, Tractors & Towering Pizza — A Day in Moose Jaw
We eased into the morning today, planning to grab breakfast at the hotel restaurant (not included)—until we realized it didn’t open until 8:00am. We wandered up the street to Tim Hortons, a well-known Canadian coffeehouse chain, where we discovered their bagel BLT sandwiches (a surprisingly solid find). A man outside asked us for money, but we politely declined and carried on. Breakfast hit the spot, and we strolled back to the hotel with coffee in hand.
Morning Wanders & Moose Jaw Discoveries
Harrison began his morning solo walk through the beautiful park next to the hotel, which featured several memorials to World War I and II—quiet, reflective, and well-kept. From there, he wandered deeper into town and discovered that Moose Jaw has its own minor league baseball team. The streets were buzzing with high school students heading to class, and he ended up doing a good bit of exploring, getting a real feel for the town’s rhythm and personality.
Western Development Museum
Later in the day, we visited the Western Development Museum, which turned out to be a fascinating look at Moose Jaw’s early days. From vintage snowmobiles to early aircraft, the exhibits were packed with history and quirky charm.
Underground Secrets
Then came one of the day’s highlights: the Tunnels of Moose Jaw—specifically, Chicago Connection – The Al Capone Experience. The Tunnels of Moose Jaw are a network of underground passages that date back to the early 1900’s. Originally built as steam tunnels for heating and maintenance, they later became infamous for their use during Prohibition in the 1920’s, serving as routes for bootleggers to transport illegal alcohol. No photos allowed (though Harrison may have snuck one or two), but the tour was fully immersive, with actors in character guiding us through the story. First, we met Fanny, a flapper-era businesswoman who introduced us to the world of Prohibition-era smuggling. Then we were handed off to Gus, our underground bootlegging guide, who taught us how to sneak goods across the border. The tour started on one side of the street and ended on the other—entirely underground. It was theatrical, fun, and surprisingly informative.
Pubs & Pizza Perfection
After the tunnels, we stopped at Bobby’s Place Olde World Tavern, a cozy Scottish pub, for a couple of beers and some snacks. The vibe was laid-back, and it was the perfect spot to unwind after a day of walking and storytelling.
Dinner was at Houston Pizza, where we ordered the “traditional all dressed pizza” – a deep dish ten-inch pizza stacked with nine toppings—seriously, this thing was an inch and a half thick. They had a full menu besides pizza, but we knew leftover pizza would serve us well for lunch the next day. We stuffed ourselves with four slices between us and saved the other 8 for the road. Thanks goodness we didn’t order the 14″ or the 18″! That pizza ended up being our lunch for the next two days, and honestly, we were crazy about it!
Moose Jaw surprised us today—with its quirky history, hidden tunnels, and towering pizza. Tomorrow, we hit the road again, but this little prairie town definitely left its mark.
Day 11: Prairie Roads, Prairie Dogs & BBQ — From Moose Jaw to Medicine Hat
We left Moose Jaw early this morning and headed straight into the heart of the Saskatchewan prairie. The landscape opened up into vast grain fields, scattered with the occasional empty farmhouse or schoolhouse, reminders of a quieter time. It’s the kind of drive where the horizon stretches endlessly, and the sky feels bigger than anywhere else.
Grasslands National Park Adventure
Our destination was Grasslands National Park and we make our way to the Visitor Center. It turns out the entrance to the backcountry scenic drive was about 15 miles back in the direction we’d just come from—so we doubled back, but not before stopping for gas at one of the most unusual stations we’ve seen.
Picture this: a massive above-ground fuel tank, probably 5,000 gallons, sitting alone in the prairie. You walk into a tiny room, swipe your card, preauthorize your amount, and then head back out to pump—no attendants, no other cars, just you and the tank. It felt like a scene from a prairie noir film. The charge didn’t show up on our credit card for a week.
Back on the road, we entered the park and made our first stop at the prairie dog town—dozens of little heads popping up and chirping at us. We tried to spot buffalo, but they were elusive today. Instead, we found a scenic valley overlook, where we settled in for a picnic lunch (that yummy 1.5″ deep dish). Nearby, a couple was searching for something they’d lost—no idea what it was, but they were determined. We ate at a quiet picnic table, surrounded by wind and wide-open views.
Backcountry Roads through the Prairie
After lunch, we continued through the backcountry loop and eventually made our way back to the highway. The drive was peaceful, remote, and full of that prairie solitude that makes you feel like you’re the only one out there…until you run into a herd of cattle trying to share the road.
Medicine Hat Arrival
By late afternoon, we rolled into Medicine Hat and checked into the Comfort Inn. Quick and easy. Then we headed out for dinner at Montana’s BBQ & Bar—a regional Canadian restaurant with hearty portions and smoky flavors. It was the perfect end to a long day of driving and exploring.
From prairie dogs to prairie skies, today was all about wide-open spaces and unexpected finds. Tomorrow, the road calls again. But for now, we’re full, settled, and ready for a good night’s sleep in Medicine Hat.
Day 12: Dinosaurs, Badlands & BBQ — A Day in Drumheller
We were up and moving by 7:30am this morning, heading down to the hotel breakfast buffet for the usual suspects: English muffins, Canadian bacon (aka ham), and a cheesy little omelet thing that made for a decent breakfast sandwich. Nothing fancy, but it did the trick.
After a quick return to the room to get properly dressed and packed, we hit the road. Today’s first destination: Drumheller, home of the Royal Tyrrell Museum, one of the best dinosaur museums we’ve ever visited.
North Through the Prairie
The drive north took about 2.5 hours, winding through more wide-open prairie. It’s a peaceful kind of drive—endless fields, big skies, and the occasional grain elevator breaking the horizon. As we arrive in Drumheller, we see the worlds largest t-rex (or so they say).
Royal Tyrrell Museum
When we arrived at The Royal Tyrrell Museum of Paleontology, we were surprised by how busy it was. Then Nancy reminded me: we’re not far from Calgary, it’s Friday, so weekend crowds make sense.
The museum takes its visitors on a 3.9-billion-year journey through time. As the only Canadian museum dedicated exclusively to the study of ancient life, it features one of the world’s largest displays of dinosaurs. While their collection boasts 160,000 catalogued fossils, the museum displays approximately 800 fossils including the world’s most complete T-Rex skeleton! We learned that roughly 60 to 66 million years ago, Alberta Canada was part of a lush coastal plain bordering the Western Interior Seaway that split North America from the Arctic Ocean to the Gulf of America. What makes Alberta especially significant is the exceptional preservation of their remains. The region’s sedimentary rock layers were formed by debris from the newly formed Rocky Mountains that deposited in ancient rivers and floodplains. Over time, these layers hardened into rock, protecting fossils from erosion. The dry climate of modern-day Alberta has since exposed these layers making fossil excavation possible and plentiful.
We spent about three hours inside, completely absorbed in the exhibits that are organized by geologic eras. The dinosaur skeletons and fossil displays were top-notch—massive, detailed, and beautifully presented. It’s easy to see why this place is a must-see for anyone even remotely interested in prehistoric life.
Dinosaur Provincial Park
From there, we headed south to Dinosaur Provincial Park, snacking on a couple pieces of beef jerky along the way. We rolled into the park around 3:30pm and immediately dug into the last slice of pizza from a few nights ago—our trusty road trip MVP, which had now served us for three meals.
We checked out the Visitor Center, which had a small but informative dinosaur display (just $2 to enter). The park itself is part of the Royal Tyrrell’s research area and is one of the most significant dinosaur fossil sites in the world.
After the visitor center, we drove the loop road, stopping at several scenic pullouts. At one stop, we hiked down to a dinosaur quarry, where many major discoveries have been made. The hike wasn’t too long or difficult, but it was classic Canadian Badlands terrain—rugged, dry, and full of character. It took us about an hour and a half round trip, and it was well worth it.
Back to BBQ & New Friends
We got back to the hotel around 6:00pm and, not wanting to overthink dinner, walked back over to Montana’s BBQ—again. It’s close, the food’s solid, and we’d had a great time the night before (plus there was only one other option within walking distance).
This time, we met a bartender named Gil who ended up chatting with us for quite a while and even bought us a round of beer. We swapped travel stories, shared photos, and even got a picture together. It was one of those spontaneous, genuine conversations that make travel so rewarding.
Eventually, we wandered back to the hotel, flipped on the TV for a few minutes, and promptly fell asleep—another full day in the books.
Summary
We had an absolute blast crossing Canada and visiting friends here so far and there is more to come.
The trip continues here:
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