A Comedy Festival in Winnipeg: Days 1 & 2

By: Samie

Travel Dates: July 18th-22nd, 2024

Days 1 & 2

(Fargo, Supper at Harold’s, Crossing Canadian Border, Alleyways in The Exchange Street Market)

Despite already having two amazing trips under our belts for our 2024 summer (Washington D.C. and Nashville), we still had one destination left before our summer started to wind down.

A little backstory: one of our favorite comedians is Nate Bargatze, and we had been wanting to be able to catch a live show of his for quite some time, but none of the dates and locations had quite worked out. The closest we had come was when he came to Sioux Falls, but it was a week night, and one of the last days of the academic school year for me, so taking time off wasn’t an option, and it would have been an extremely late night trying to drive back home for work the next morning. When searching for an alternate show, we discovered that he would be making an appearance for the Great Outdoor Comedy Festival in Winnipeg, Canada!

Despite being a whole other country, the Canadian border is actually not all that far from where we are. For a little perspective, it’s about a 5 1/2 drive across the state if we wanted to visit Rapid City. It is about a 5 hour drive to the Canadian border and just over a 6 hour drive to Winnipeg. That means that we could drive into a different country and still consider it a “local” trip for our rotation since it’s easily within the 12 hour drive window from where we live!

To make this tantalizing adventure even more tempting, Luke’s sister, Annie, lives in the Fargo/Moorhead area, so we would be able to drive up the 3 hours to see her, and then finish the other 3 hours to Winnipeg, making it a very nice and split up drive. So we decided to extend the invitation to Winnipeg and the comedy festival to Annie and Luke’s parents so that it could be a fun family adventure! Despite Luke and I being together for 8 going on 9 years and being married for 4, we had yet to embark on a family adventure with his side of the family. With how spread out my side of the family is, we had already been fortunate enough to enjoy a couple different trips with them with more likely on the horizon, so some extra time with Luke’s wonderful family was far past due.

The first leg of our journey began on July 18th. Luke and I did drive separate from Luke’s parents, but we all met up at Annie’s house. We spent the afternoon tackling some house projects before heading over to Duck Duck Goose Food Co., a food truck that parks outside of Harold’s on Main, for some supper. The food truck offers a beautifully reduced menu of three main entrees and one dessert. The three options were Pad Thai Fries, Tater Tot Hot Dish Nachos, or a Smash Burger. Annie and I opted for the delectable-looking Pad Thai Fries, Luke and Mary ordered the Smash Burger, and Dave went with the Tater Tot Hot Dish Nachos. We got to sample a little bit of everything, and it was all absolutely delicious. We also had to order the dessert, Lemon Doughnuts with Blueberry Ice Cream (UNSPEAKABLY amazing).

For drinks, we stopped into Harold’s. Beers were the popular beverage of choice, but Luke and I also wanted to try a couple of their cocktails. Luke got a Whiskey Fairway Smash which is rye, rosemary simple, lemon juice, and pomegranate shrub. I got a an Aperol Papa Pancho which is aperol, peach liqueur, grapefruit juice, and Prosecco. They were both satisfyingly refreshing and tasty!

The next morning, we departed the Fargo/Moorhead area a little before noon in order to enjoy a more relaxing start to the day. There was a stop we wanted to make for lunch in Grand Forks, so this put us there around 1:00. The place we stopped is called Bernie’s, located in East Grand Forks. It is a cafe, bakery, and market that offers lots of well-known Midwest dishes and ingredients!

Right away when we walked in, the bakery items on display looked far too tempting, and we knew we would be leaving with a few in hand before we departed. First, however, we sat down to order a meal of more sustenance. Much of the menu was eye-catching and made choosing what to order quite the quandary. Luckily, we were all able to pick out something that we fancied. I must admit that I can’t recall everyone’s order, but I do know that it all looked wonderfully appetizing! I remember that I ordered The Bernie, a sandwich with ham (or turkey), brie, lettuce, giardiniera and vinaigrette on focaccia. I also am certain that Luke ordered a bowl of their knoephla soup, as it is one of his favorites. For a sandwich, I believe he ordered The Piglet, which is ham and mayo on a croissant. Wracking my memory, I think there were a couple of patty melts on the table as well. However, it’s worth checking out the menu yourself because there were no wrong answers!

The next leg of our journey to Winnipeg was to cross the border into Canada. This may have been the part I was most excited about because I had never crossed a land border before, and I had only used my passport for the first time the previous summer when Luke and I finally took our long-awaited honeymoon to Iceland and Norway. Even then, we only actually used them once because you can move between the Scandinavian countries without the use of the passport, so I was giddy at the prospect of getting to use it again!

As we approached the border, we joyfully (or I did at least) took out our passports to hand to Luke, who happened to be the one driving, so that he could hand them all to the border patrol officer at once. The line was decently long, but it was also a pretty easy entrance for us. He asked a few questions and took a look at each passport or I.D. and confirmed that he saw each correct person in the vehicle, and then we continued on our way, officially in Canada! Unfortunately, we didn’t receive a stamp for our passports, so despite now visiting 3 different countries, I still only had one stamp. Oh well!

We continued our way a little bit deeper into The Land of Maple, until we finally were making our way into the city of Winnipeg. Our first order of business was to make our way to our Airbnb to get settled before adventuring out for the late afternoon/evening.

I had little to no information on the area, so when booking our stay, my goal was simply to find a well-rated house that would accommodate all 5 of us comfortably. This lead me to a little house with 3 individual bedrooms, 2.5 baths, and a high 4.78 rating. Although the location reference meant very little to me, this amount of space for the rate they were asking seemed too good to pass up.

We quickly learned that our Airbnb was almost on the opposite side of where we had entered the city. Despite only being about a 10 minute drive from downtown, it was quite the drive to get into downtown, through downtown, and then another 10 minutes to our Airbnb. We also, unfortunately, discovered that while a quiet neighborhood, the location of our Airbnb was not exactly in the best-kept neighborhood. It was definitely a more run-down area, but where we were staying was a little tucked away from the main road, and we felt perfectly safe and secure, so it was all fine in the end, but I definitely felt a little guilt since I had been the one to pick the place!

Our place was well-equipped for a comfortable stay with a garage to keep our vehicle in and a keypad to enter. It was very nice and clean, and we were each able to pick out a room to stay in! Luke and I took the room and space in the basement, while Dave and Mary took one bedroom off the living room upstairs, and Annie took the one closer to the kitchen. We all settled in and relaxed for a little bit before we were once again ready to set out and do some exploring before calling it a day.

Something I had come across while looking into some things we could fill our time with while in Winnipeg was a local event called Alleyways in The Exchange. It only takes place during the 3 summer months (June, July, and August) and only on the third Friday of each month. That means there are only 3 of these events held every year. Our arrival just so happened to coincide with the timing of the July market, so it was immediately added to our itinerary!

During Alleyways in The Exchange, curated markets and pop-up installations fill the streets of 4 different alleys within the Exchange District. Each alley has a different theme depending on what you’re in the mood for. There’s a Market Alley, Sounds Alley, Lounge Alley, and Tango Alley. The Market Alley is filled with vendors selling hand-crafted items, snacks, and locally sourced foods. The Sounds Alley is where you would go if you are seeking installations or live performances in all forms from jazz to electronic music to poetry to sound and visual art! The Lounge Alley is where you would find a more artsy and divey vibe, such as pop-up bars, DJs, and immersive art. Lastly, the Tango Alley is a great stop if you’re looking for a fun place to watch, participate, and just experience the vibrant and classic Argentinian tango dancing!

While all four alleys brought their own fun and flavor, we were mostly interested in The Market Alley, so that’s where we spent our time. The district was definitely busy and pack, and finding a place to park was a bit of a challenge. We were, however, able to find a spot in a paid lot not to far from where the market was set up. We made the short walk over to an entrance into the alley and were immediately overwhelmed by people and vendors. There was so much to take in that we initially just made a quick walk through without really stopping or turning down any of the side streets. We had arrived around supper time, and while there were many vendors offering delectable-looking sweets and treats, there didn’t appear to be a place that offered a solid meal, so we decided to find a place that we could sit and eat first and then would return to the hub of the market to shop.

We made our way to an eatery across the street called Saddlery. We were all feeling something a little more light, so we decided to order a charcuterie board to share. The board came filled with cured meats, cheeses, house pickles, local honey, and grilled baguettes. Luke and I are already pretty big fans of charcuterie boards, and this one was especially delightful. I, in particular, enjoyed the local honey!

Once our tummies were lightly filled, we were ready to give the market another walk about and actually take a loot at what this unique event had to offer! We split up to wander to areas that interested us the most. Luke and I came across a vintage vendor, and I saw a gorgeous blue glass-blown purse. I had seen items like it while scrolling through reels and wanted to own one myself, but hadn’t come across one back home. Plus, we usually fly when we travel, and it wouldn’t be something I would risk attempting to fly with. However, here one was, in my favorite color, reasonably priced, and we had driven instead of flown, so I would be able to bring it home safely! It definitely was quickly in my hands and paid for.

I had also seen a cotton candy stand, and I absolutely love cotton candy. Believe it or not, I used to be a figure skate and would participate in my home-towns local ice shows. One of my fondest memories of these shows is that when they were all over, they would come back to meet the performers with a huge garbage bag of all the extra cotton candy that hadn’t been sold, and we would be able to take a couple home! This left a very special place in my heart for this sweet treat, and I try to indulge whenever I can! This stand has some especially irresistible flavors, and I ordered a large sweet mango. I was pleasantly surprised at how big the large actually was and turned more than a few heads as I walked down the alley with it.

Cotton candy was our last stop before we had agreed to meet back up with the rest of the family to make our way back the car. We had stopped at many of the available vendors during our hour of exploration, but I am selfishly sharing my favorite two stops. We walked back over to the vehicle and drove back to our temporary home to relax with some TV and lovely company for the evening after our long and full day of travel. We still had lots to look forward to and wanted to be well-rested for the remainder of our adventure, so we called it a night and slept as well as we could for the next day we had ahead of us!

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