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September 28, 2023

Built to discover. Those words form the ethos of Oak & Oscar’s approach to both designing timepieces and developing and fostering community. We believe watches are built to be worn, not to sit in a box — they’re tools to help you see the world and explore everything it has to offer. The wonderful people that make up the community of Oak & Oscar Owners share this perspective.

In the spirit of the explorers, builders, and dreamers after whom our watches are named, we thought there would be no better way to celebrate our vibrant and growing community than by setting out into the wilderness of southwestern Wisconsin for a weekend of locally sourced cuisine, exploration, good conversation, and fly fishing.

To satisfy this drive to explore, we’re developing a series of Owner-focused “Built to Discover” trips that’ll see us heading to interesting locales, eating good food, drinking good bourbon, and talking watches. For our first Built to Discover trip, a group of 14 Owners traveled up to Wisconsin’s Driftless Area. Known as “the land the glaciers forgot”, the Driftless Area is a unique landscape with lush vegetation, steep hills, and pristine waters. During the last ice age, glaciers flattened everything in their path as they slid south. But they spared this singular area of the Midwest, leaving behind a beautiful collection of meandering streams and lakes and steep, jagged hills. Known for its excellent fly fishing, we thought this would be the perfect place to get away from the hustle and bustle of the city and spend some time with good friends.

A disembodied head of a brook trout on grass
David Fason laying on a hillside poised to take a photo

Accommodations for the weekend were at the Red Clover Ranch, a 79-acre piece of wooded paradise located in Soldiers Grove, Wisconsin. Red Clover is the distinctive vision of Annie Coleman, a honkytonk band leader, former corporate banker, real estate company founder, and creative visionary. The Ranch was inspired, in part, by the Golden Horse Ranch, a dude ranch and resort that was owned and operated by Coleman’s grandparents.

With Red Clover Ranch, Coleman sought to create the same sense of community and attachment to the natural world that her grandparents fostered. It’s safe to say, she hit the mark. Complete with a firepit, cabins built with lumber harvested right from the property, and an amazing kitchen that prepared meals with ingredients sourced from the land and local purveyors, Red Clover Ranch was the ideal location for the weekend. Guests were treated to a vibrant blanket of stars in the evening and glowing sunrises during the cool mornings.

Fish laying on its side in water being released from a fisherman
Trout partially in water laying in a fishing net next to a fly fishing rod

Our first evening in Soldiers Grove was unexpectedly humid. Despite spending many summers in the South Carolina heat, even I had to change into something a little better equipped to deal with the thick moisture in the air. That didn’t deter us from having a lively welcome reception for everyone in attendance.

 Before dinner, the more experienced anglers in the group kindly put on a casting demonstration. The mechanics of fly casting are deceptively difficult — though the motion appears simple at first (merely bring your arm back and then swing it forward), the difficulty of striking a proper balance between strict arm control and a relaxed attitude is not as easy as it seems. Owner Brad E., one of the more accomplished fly fishermen in the group, explained that you don’t want to feel like you’re working too hard when you’re fly fishing.

Work, after all, should be left in the office and not brought to the stream. All these considerations occur well before you need to worry about getting your line tangled or hooked on a submerged log.

Once we consumed an appropriate amount of ice-cold beverages and everyone had a chance to get at least nominally acquainted with the art of casting a fly line, we gathered for dinner in a screened-in porch that afforded beautiful views of the natural landscape, foraging goats and all.

The meal was wonderfully prepared and featured a salad with locally sourced vegetables and handmade pizzas cooked in a wood-fired oven right there on the porch. Local wine and craft beer from nearby breweries rounded out the experience.

As part of the place setting, Chase presented every Owner with a custom fly box of three hand-tied flies that would be used on the water the following morning: an orange zebra midge, a pink squirrel, and a fuzzy hippie stomper.

Side note: Having watched Chase tie many of these flies in the office in the weeks preceding the trip, I can attest that this is a painstaking process. The act of gifting a hand-tied fly is a special gesture and is one that isn't taken lightly in the world of fly fishing. It's a sign of respect and appreciation, something we feel very strongly about the Owners here at Oak & Oscar.

After dinner, bourbon was poured, friendships were forged, and old ones were rekindled. Because the summer had been so hot and dry, our fly fishing guides insisted that we be at the fly shop no later than 6 a.m. That meant a relatively early night for all but the heartiest among us. The good folks at the Driftless Angler are experts in their craft, so we didn’t argue.

The Driftless Angler is one of those shops you read about. Both locals and visitors come here to swap fishing stories, trade secret fishing locations, and brag about the size of their latest catch. The local fly shop serves as a place of community for the entire surrounding area and should be on anyone's fly fishing bucket list.

Surprisingly, everyone made it down for a quick breakfast and coffee by 5 a.m. after which we loaded up the vehicles and headed to the Driftless Angler to commence our morning of fly fishing.

For my part, as a total neophyte to the world of fly fishing, I wasn’t quite sure what to expect. Would we all venture into the stream together? At the very least, would we be roughly in the same area? Would I be able to avoid getting my line caught in the seemingly never-ending brush that surrounded the streams? I suspect similar questions were running through the minds of my fellow newbies.

The answers to these questions came swiftly as the guides split us up into groups of two, with one experienced angler and one novice. We promptly departed the fly shop and were driven by our guides to far flung and, I gathered, somewhat secret spots to fish for the remainder of the morning.

Overhead shot of a river cutting through marshy land
Fish in the foreground with a sunset in the background, illuminating the fish's fins
Overhead shot of a river cutting through marshy land
Fish in the foreground with a sunset in the background, illuminating the fish's fins
Fish in the foreground with a sunset in the background, illuminating the fish's fins

I was paired up with Owner Matt C., an experienced fly fisherman, former Chicagoan, and current denizen of Bozeman, Montana. Jake, our fishing guide, clearly knew what he was doing. He’s been fly fishing since the age of ten, so he had a few decades under his belt.

 It wasn’t until we arrived at the stream that the true beauty of the Driftless hit me. It was still early enough that the sun hadn’t yet baked away the morning mist that blanketed the landscape.

With the sun cresting through the trees and not another soul in sight except for my companions and a few chirping birds, the magnificence of the undisturbed woodland washed over me. Judging from the photos captured of others that morning, I would be willing to bet that all of my compatriots had a similar experience.

We could have stood in awe of the landscape all morning, but there were fish to be caught. Trudging through the brush, our waders acted as suits of armor, rendering us impervious to the prevalent thorns and cow parsnip. It’s also worth emphasizing the impressiveness of waders: how awesome is it to submerge yourself in the cold waters of a trout stream without getting wet!?

Our group met with varying levels of success. I managed to get several bites but netted only a small chub and a single brown trout. Owner Luke W., an Air Force serviceman hailing from Ohio, hooked himself a brook trout (which is no easy feat). Owners Jeff “Hoff” H. and Brad E. duked it out for most fish caught during the day (this would turn into a healthy debate as to who actually snagged the most fish at dinner later that evening).

After an incredible morning on the water, we all reconvened in quaint downtown Viroqua, WI for lunch at Noble Rind, a charming bistro that also supplies food to the adjacent Hotel Fortney. As should be clear from their name, this place has a cheese selection to die for with wheels of funky blue and sharp cheddar cheeses lining the front display case.

Following a recharging, hearty lunch, we made a short trip down the road to meet the wonderful folks at the Wonderstate Coffee Roastery for a private tour and tasting. We were treated to sips of virtually all the varieties of coffee produced by Wonderstate as well as the opportunity to see their 1930s-era roaster in which their small batch coffee is roasted to perfection. Sipping each and every type of coffee on offer allowed us to get a real sense for the subtle differences that distinguish the flavor profile of a light roast from a medium or dark roast. Plus, the burst of caffeine-infused energy helped diminish the effects of the bourbon still lingering from the night before.

With a highly anticipated dinner at the Driftless Café scheduled for 8:30 p.m., the rest of the afternoon allowed us some time to do our own thing. Some folks went back out on the water to try to catch one last fish while others went back to the ranch to relax.

After a beautiful afternoon, we once again headed to Viroqua for our dinner date at the Driftless Café.

You wouldn’t expect a small town like this to have such a high-caliber restaurant, but let me tell you, it may be worth it to travel to Viroqua just to dine here.

The menu is ever-changing; dinner offerings often aren’t finalized until just a few hours before service, ensuring that only the freshest ingredients are used. The Café features a smorgasbord of options sourced from a collective of local farms. From savory to sweet, the kitchen at the Driftless Café does everything well.

 We likely overdid it with several rounds of passed appetizers, salads, main courses, and dessert, but, as Veronica Corningstone would say, “When in Rome”!

The temperature dropped considerably by the time we returned to the Ranch for the evening. Conditions were perfect for the firepit — something that would have been unthinkable in the heat and humidity of the previous night. We poured bourbon into our custom Oak & Oscar Yeti tumblers and settled in next to the warmth of the fire, gazing up at the stars and savoring the moments before the impending return to everyday life.

For our final morning in the Driftless, we gathered one last time on the screened-in porch for a filling breakfast featuring perhaps the best bacon I’ve ever had in my life, among other locally sourced goodies. Everyone received a generous swag package from Fish Hippie provided by Owner Dave F., our resident photographer for the weekend (read his owner story here). Once we snapped a group photo, we begrudgingly prepared to go our separate ways.

Some of us decided to get one last bit of fishing in; others needed to return to their normal lives.

This remarkable experience showcased how special the Oak & Oscar Owners community really is.

It’s made up of folks from many different walks of life, from places all over the globe. Indeed, to be an Owner is to be part of a group that loves exploring, seeks out new experiences, and cherishes lasting friendships.

We make no little plans here at Oak & Oscar, so we’ll be doing more of these Built to Discover trips in the future.

In fact, mark your calendars: we’re heading to the Boundary Waters of northern Minnesota in early spring 2024. We’ll also likely explore the famed Bourbon Trail later in the year and sample some of Louisville’s finest.

 We can’t wait to share more of these awesome experiences with you. In the meantime: make no little plans, keep exploring, and get out there and discover something!

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.  

Oak & Oscar Owner Story, overhead shot of a river winding through a forest