Winnipeg Trip Recap

A play-by-play of a YWG friends and family reunion

After 19 months without seeing my parents, and over 2 years since setting foot in my homeland of Winnipeg, Manitoba, Canada, I finally took 10 days off work and was able to cross the border safely without quarantining, to return home to visit family and friends, and celebrate my Granny’s 100th birthday!

This trip was different for many different reasons. First, I wasn’t staying at the old stomping grounds of 203 Mayfield (my parents’ former home), but instead was a guest in their brand new condo, Roblin Grove. Second, I was home at the same time as my sister and her family, making it a tight squeeze in the new digs, but a ton of fun. Third, I brought Lynn along for the ride to experience the gong show that is a trip home to Winnipeg for me.

In the year or so we’ve been dating, I don’t think our calendar has ever been so packed with activities, lunches, dinners, golf games and meetups, but it was a massive success. Without going into every detail, here are some of the highlights.

Friday, August 20th

Covid traveling was no problem, even with a Luxembourgish passport. We had our negative tests and our proof of vaccination, and we were all set. New York to Toronto was a breeze, and after some serious delays out of Toronto (and my golf clubs deciding to stay in Pearson airport for a few extra nights), we arrived at Roblin Grove to greet my parents and sister who graciously stayed up past midnight to say hello.

Saturday, August 21st

The morning started the best way possible. After a 6 hour sleep, we were greeted with a knock at the door by my nephew Finn (who had already been there for a week) to give us a big hug. It was so amazing to be around him for 10 days, and see how much he’d grown and learned since I last saw him in November. Over the course of the trip, we played cards, did puzzles, built LEGO, went for walks, played on playgrounds and watched plenty of fun movies.

After playing with Finn we went to pickup Steve (my brother in law) from the airport for his Winnipeg week to begin. Then we went over to our family friends the Keating’s house for a swim - Finn loved the water, backing up his name. We had some tasty BBQ food, snacks and a few beers before heading over to the local Thirsty Lion pub for a traditional meetup with some of Dan and mine’s oldest family friends Tracy and Dani. Plenty of laughs and a few Keith’s pints were capping off a tiring first full day, or so I thought.

As we were paying the bill, a couple of my friends Derek and Eric captured me in the parking lot as they were going back to Keating’s to meetup with Chad and the boys (Chad hadn’t left since we were swimming there). I couldn’t say no, so we dropped Lynn off at the condo (she was understandably tired) and we went to Keating’s basement where we have spent so many hundreds of hours. It was great to see the guys, catch up a little bit, and hear how they’re all so happy and dominating life. Even Dean (Chad’s dad) was so excited to see us all together that he insisted we shotgun a beer on the back deck - nobody refused.

Sunday, August 22nd

I took Lynn over to meet my Granny for the first time. Even at 100, she’s a great conversationalist and made Lynn feel so welcome. We had lots of laughs, listened to her stories, and talked with her and my Aunt Louise about the big plans for the upcoming celebration. Over two hours flew by while we were there and I was so glad Lynn got a chance to meet Granny for a proper visit before the rest of the hectic week unfolded. Leaving Granny’s, I had to take Lynn to the St. James staple Sargent Sundae while regaling her with all the memories I had of my grandpa taking me and Dan there.

We ended the night with a traditional Sunday family dinner. It doesn’t sound like much, but it was so special to sit down and have a nice meal with the 7 of us, followed by some ad hoc Trivial Pursuit. For those readers who live near your families, don’t ever take Sunday dinners for granted - this was one of my favourite memories of the trip.

Monday, August 23rd

After coffee and playing with Finn, Dan, Finn, Mike and Lynn headed for Winnipeg’s famous landmark, the Forks. There, we met up with my buddy Tyler who was strolling around with his two year-old Kiba, who I hadn’t yet met. It was fun to walk around, have Finn and Kiba explore, and catch up.

For lunch, Dan, Lynn and I hit up another Winnipeg landmark, Boston Pizza for lunch. I say that sarcastically, but it really is a hot spot for memories, and because we don’t have BP’s in New York, it was cool to share some cactus cuts again.

For dinner, the kids all went to Tracy’s for some sushi and craft beer and cards. Finn played a memory game and Go Fish with us, and seemed to really enjoy the evening like the rest of us.

Tuesday, August 24th

Steve and I were supposed to golf with my dad, but the weather, which had sucked all week, rained us out. Instead, Dave and I took Steve, Finn and Lynn on a driving tour of our beautiful city. Dave drove and I played tour guide from the back seat. Stops included Assiniboine Park, Little Italy, Confusion Corner, the University of Manitoba, and every bar I could remember that served me at least one beer during my university days.

The evening was planned well in advance as my “Aces” friends had organized our Fantasy Football Draft that night to coincide with me being home, despite it being a couple weeks out from the league starting. We dropped Lynn at Britni’s who was gracious enough to play hostess, I got to meet her daughter Ella finally, before Eric and I headed out to Derek’s house to begin the draft. After a delicious veggie burger and fries from George’s Burgers (thanks Nik), a few pints of Keith’s and tons of laughs with the guys, I was heading home with a mediocre fantasy team, and a heart filled with the value of friendship.

Each time I saw one of my friends this trip, it was a clear reminder of how incredibly close we are, because the conversation and needling flowed like we hang out every weekend, when really I hadn’t seen most of them in over 2 years.

Before heading home, Lynn and I caught up with Eric and Britni a bit more in their new home which made for a lovely cap-off to a great Tuesday.

Wednesday, August 25th

Chad Keating’s birthday. Lynn and I took Finn to the nearby playground where he showed us his rock climbing and sliding skills before explaining the entire plot to Wizard of Oz on our walk back to the condo. Then we went to meet Chad and a few buddies for a brewery lunch to celebrate 35 years on this Earth, before I had to jet and meet the guys for Men’s night golf at my home club.

Every time I go back to Breezy (where I worked for 6 years and played golf for 7), it’s great to see so many familiar faces, play golf with friends or family, and generally just feel so at home. I ran into my old boss, and countless friends. Almost everyone from the regular Wednesday squad showed up, and 10 of us played in two five-somes. At least in my group, there were countless laughs, a few birdies, and maybe some on-course libations.

After the round we went back to Britni and Eric's to meet all the WAGs and I was so happy to see how many friends gave up their Wednesday evenings, arranged babysitters, and changed plans just to hang out with me and welcome Lynn to Winnipeg. Huge shoutout to Eric and Britni for hosting and providing incredible vegan tacos! I’m sure Thursday morning was a little slow for everyone who was working the next day, so I’m truly grateful for the sacrifice.

Thursday, August 26th

This is when the focus of the trip shifted back to family, as members from across Western Canada began to arrive for the 100th birthday celebration. We headed over to Granny’s again to see my Uncle Don who had arrived from Vancouver and visit a bit longer. Then we smashed a little spaghetti and vegan meatballs back at the condo before heading to my friend Tyler’s ultimate frisbee game where I got to catch up with Yacine and Quinn, two friends I became really close with over Zoom throughout the pandemic. We shared some great stories, and I got to finally meet Yacine’s wife in person as we took Lynn to another iconic Winnipeg event - Smitty’s wing night!

Then we picked up Dan and Steve from Dan’s good friend Tracey’s - it was so nice to see another group of people I’ve known for over 20 years, tour their (relatively) new home, and help Dan and Steve out with a friendly ride.

Friday, August 27th

After getting a Covid test (to prep for our flights home), we utilized the BBQ again at the condo and made some tofu steaks to be enjoyed with a Dwenda special - the oriental noodle salad - for lunch. After lunch, it was back to Granny’s to catch up with even more family who had arrived from Alberta and Kelowna. It was great to chat with my Uncle Keith and Uncle Jim, cousin Jimmy and his family, play with Finn, and just generally hang out as an extended family which is super rare.

Before dinner, I headed out for another event that was planned well in advance. I met my golf crew and their significant others for an amazing dinner downtown at Hargrave Street Market. I crushed a delicious vegan pizza and had so many laughs sitting right between all the guys and all the girls. It was Andrea’s only day off basically all month (her event planning business weathered the Covid storm and now had two years of backlogged weddings to work through!) so I was super happy to spend some time catching up with her and the rest of the crew. The end of the night took us back to Sean and Jill’s house (which I also had not seen) which was stunning, and allowed us to have another hilarious night cap.

Saturday, August 28th

The day of the big celebration had arrived. Dan and I went to pick up some last minute supplies for the afternoon gathering to celebrate my Granny’s 100th. Even though she turned 100 back on April 29th, traveling back to Manitoba for all the relatives wasn’t feasible at that time, so we pushed it to August once all of the quarantine rules were relaxed and everyone could be fully vaccinated. We picked up sushi (doesn’t your 100 year old grandma like sushi?), balloons, cupcakes, and we were all set!

The party was a huge success - we snapped some great photos, Granny was looking sharp, and she was so happy to have all of her family close by. We ended the night with a family dinner at Silver Heights (best ribs in town) before saying goodbye to all of my family, especially Granny. It’s always hard leaving Winnipeg, and hugging Granny goodbye is often the hardest part.

We capped the night off with a quick hang with my cousin Chelsea, who I hadn’t seen in a few years, and who is hilarious. It made me think that one of the best parts about growing a little older is how much more you can relate to cousins, even if they’re, say 5 years older or younger than you. When you’re young, 5 years can make a world of difference, but now, we can chat about relationships, careers, and really anything. It was a great way to cap-off the extended family agenda.

Sunday, August 29th

Coincidentally, the Breezy Bend Member Guest golf tournament landed during this week so I was able to tee it up as my dad’s partner. We were paired with the Reyda’s: Court, who used to coach me volleyball for years, and Andrew, who I used to play Breezy Bend with nearly every day from 2003-2005.

While we didn’t play great, we had lots of fun and my mum brought Lynn to the course to pick us up, so I was able to introduce her to a ton of members, staff, and provide her with yet another tour of my old stomping ground.

After a final Sunday dinner, and toast to a great trip, I did one last puzzle with Finn before getting to bed for an early departure. It sucked saying good bye to Dan and to a very tired Finn in the morning, but I know I’ll see them again very soon.


The trip gave me exactly what I needed. I was filled with joy and gratitude for the amazing family and friends I have, was happy to spend so much time with my parents in close quarters, to play a ton with Finn and to introduce Lynn to probably a hundred new people - I think she’s finally recovered.

I love so many people in Winnipeg that it sometimes makes me question living away, but I was also happy to see the skyscrapers of NYC as we took a cab from La Guardia back into Manhattan. Thanks to everyone who hosted us, bought us drinks and food, made plans and arrangements ahead of time, and took time to say hi!

Thanks for reading,