To be an Oak & Oscar Owner isn’t just about owning a watch or two...or ten (you know who you are!). Rather, being an Owner means being part of something bigger. You’re a member of a community of likeminded people who care about craftsmanship, quality, adventure, and each other.
We take pride in being able to foster this community of so many amazing people. It’s impossible to describe how cool it is that people fly in from all over the U.S. to take part in our annual Owners weekend or take time out of their weekends to compete in a chili cookoff at the HQ. Having so many wonderful folks who celebrate what we do is truly amazing.
In August 2023, we launched a new series of Owner-focused trips, dubbed “Built to Discover,” with a fly fishing expedition in Wisconsin’s Driftless Area. The response was overwhelmingly positive, and we had such a great time that we knew we were going to have to do it again!
In late September, we were joined in the Driftless by 14 Owners for another incredible weekend of delicious, locally-sourced cuisine, fly fishing, wine tasting, exploring, and talking watches and everything in between. We had a great crop of new folks along for the ride this time as well as some familiar faces. It was an amazing experience, and we cannot wait to do it again!
We arrived at the Red Clover Ranch, our home away from home, in the late afternoon on Friday. Fortunately, it was much cooler than it was the previous year. We had a few hours to get settled, get acquainted, and begin our casting demo.
Brad E., loyal Oak & Oscar Owner, friend of the brand, and fly fisherman extraordinaire kindly offered to lead the demonstration. We all got out our practice rods and began working on the mechanics of casting a fly line.
Personally, I hadn’t been fly fishing since March, so I needed a refresher. I’m happy to report, however, that casting is kind of like riding a bike. Once the muscle memory kicks in, it’s all gravy. Of course, even if you get your cast down, there are no guarantees that you’ll actually catch any fish. That’s the really hard part! 😉
Soon thereafter, we were treated to a home-cooked meal of delicious salad and pizza featuring ingredients sourced directly from the region. I know we drove this point home last year, but the food at Red Clover really is incredible. I mean, you just can’t beat pizza cooked in a wood-fired oven right on the screen porch on which you’re enjoying a cocktail and listening to the crickets chirp.
We were all up before the sun on Saturday morning. As the saying goes, the early bird gets the fish (or something like that). We joined our friends and expert guides at the Driftless Angler to get outfitted for our morning on the water. The guides have been at their craft a long time and are a wealth of information. From finding the best fishing spots to advice on the best gear, these guys are the go-to experts in the Driftless area.
There's nothing quite like being out on a stream in the early morning with crisp, early fall air rustling through the trees. It's quiet, giving you an opportunity to disconnect and focus on the task at hand. That's a rarity in this day and age which makes the experience that much more meaningful.
By and large, our day on the streams was a success! Everyone caught at least a few fish, and there were definitely some new converts to the fly fishing hobby.
After a great morning on the water, we all reconvened at the Ranch for a hearty and much needed lunch of tacos with hot salsa made from a local purveyor. Once we were all refueled and recharged, we departed for our next adventure: a private, guided tour of Las Mujeres Farm & Winery.
Las Mujeres was founded in 2019 by Tony Bezsylko. Tony is a philosopher, former restaurateur, and wine enthusiast. After opening and running one of the most successful restaurants in Chicago for many years, Tony decided to leave the hustle and bustle of the city and open a natural winery in rural Wisconsin. Las Mujeres specializes in natural wines and ciders made from ingredients grown right on the property. Tony guided us through the tangled thicket of vines, bushes, and trees that blanket the many acres of his vineyard, taking care to point out the varieties of grapes and other fruits grown on the property.
At the end of the tour, we were treated to a tasting in the wine cellar and some freshly baked bread and Spanish tortilla. Tony got his start in the restaurant business as a baker, so the bread was to die for. And the locally sourced, Amish-made, handchurned butter really solidified the experience. As for the tortilla, well...let's just say there wasn't enough to go around!
As our tour was wrapping up, black storm clouds rolled in all around us. We knew we had to head back to the ranch before the sky opened up. Luckily, we all made it back before the downpour began. It was a real treat watching the storm from the porch. The clouds blotted out the sun making it seem as if it were already night as rain drenched the rolling hills surrounding the ranch. The storm provided the perfect ambience to wind down the remainder of the day.
When the clouds parted, it was time to head to one of our very favorite places, the Driftless Cafe. This isn’t the first time we’ve mentioned the Driftless Cafe on this site, and it certainly won’t be the last. I’ve been to the Driftless Cafe a handful of times now, and it’s been absolutely amazing each and every time. Whether it’s a burger for lunch, a pizza in the late afternoon, or a perfectly cooked beef tenderloin for dinner, you won’t have a bad meal here.
As we sat around the dinner table, we all swapped fishing stories from earlier in the day and discussed gear, watches, golf, and life. It was a special moment that had us all feeling that we didn’t want the weekend to end just yet. Fortunately, the festivities weren’t quite over.
It was nice and cool when we returned from dinner. It was the perfect night to sit around the fire pit. We gathered some wood and built a roaring fire, sipped some bourbon and a few special release craft beers and kept the night going.
The next morning, we gathered for one last meal on the porch, a delicious breakfast of apple tart, granola, quiche, farm fresh salad, and the most delicious bacon on the planet (yes, it’s that good!). The torrential rain the previous day had swollen the streams to such a degree that it dashed the hopes of those looking to get in one last bit of fishing. But that didn't diminish the morning one bit.
After breakfast, we all gathered our gear, said our goodbyes, and headed home in anticipation of next year's trip.
The 2024 Built to Discover trip was an awesome experience. It was great to return to some familiar places and see some familiar faces. But it was just as cool to branch out and explore more of what the Driftless has to offer. As you know, we live by Daniel Burnham's exhortation to make no little plans, so we're always looking for new experiences that broaden our collective horizon.
If you missed out on this year's Built to Discover trip, don't fret. We'd love to have you join us on our next adventure! Stay tuned for what's in store for 2025!
Not an Owner yet and want to be part of this amazing community? Click here to learn more about our watches!
Are you an Owner? Do you have a story? Of course you do! We’re always looking to meet our Owners and share their adventures on our site and with our fans. Send us a message and let us know you’d be willing to chat with us about you and your adventures, and we’ll do the rest.
