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Let's go fly fishing!

Built to discover

Everyone had so much fun last year we’re doing it again! For our second Built to Discover Trip we’re headed back up to the Driftless Area! As you may know, The Driftless is an area in western Wisconsin that the glaciers forgot. With steep sandstone cliffs, plentiful cold water streams, and a beautiful rugged landscape, it is a world of its own.

It’s the perfect time of year to get outside and enjoy nature while trying to catch some trout on the fly! Join fellow Owners and friends of Oak & Oscar from September 20th to the 22nd for an all-inclusive weekend of fly fishing, bourbon drinking, farm-to-table dining, and an overall awesome time.

Red Clover Ranch

We’ve rented out the entire Red Clover Ranch, a beautiful 79-acre property in the Driftless Area of Wisconsin. Newly opened in spring 2023, Red Clover Ranch features stunning views of the lush surrounding woodlands.

Charming Cabins

During the weekend, we’ll be housed in recently built cabins nestled in the woods that will be perfect for getting away from it all for a few days.

Farm-to-table meals

Farm-to-table meals will be curated by one of the ranch’s in-house chefs using locally sourced, in-season ingredients.

The expansive ranch has plenty of space to relax, including a fire pit that’ll be the ideal spot to sip some bourbon and enjoy the scenery.

Fly Fishing

This trip will have something for both experienced anglers and novices alike. The Driftless Area offers some of the best fly fishing in North America, with streams and creeks that are abundant with trout. No fly fishing experience? No problem! On Friday evening, there will be a casting class and demo. And on Saturday morning, we’ll have the top fly fishing guides in the area showing us the way.

Casting Lessons

Friday afternoon, we'll spend time at the Ranch learning to cast fly rods—with a few barley pops of course!

Gone Fishin'!

We'll hit the water early Saturday morning with expert guides from local fly shop, Driftless Angler. They've got the gear and the experience to get us on the fish!

For those that want to, we'll have the chance to do some additional fishing Friday evening and Saturday afternoon.

Food and Drink

The Driftless Area is becoming well known for good quality food. With the abundance of local farms and creameries, we will be spoilt for choice. The good news is we've already arranged for an epic weekend of eating.

Red Clover Ranch

We will enjoy several meals, including Friday dinner, Saturday breakfast and lunch, and Sunday brunch, prepared by the in-house Chef at Red Clover Ranch.

Driftless Cafe

We've made a special reservation at what may be my favorite restaurant in all of Wisconsin, if not the midwest. The Driftless Cafe is a Michelin-quality restaurant that features an ever-changing menu of local ingredients. This place never disappoints and is half the reason I love Viroqua.

Las Mujeres Farm and Winery

We've also arranged a private tour and tasting at the Las Mujeres Farm and Winery in Readstown. We'll sample their wines and ciders and get a behind the scene tour of what makes them special led by the owner and founder.

Intinerary

We've planned an amazing weekend exploring the Driftless Area and all that it has to offer. Here's a basic itinerary of all the awesomeness.

All Inclusive

Leave your wallet at home

We're not kidding when we say all inclusive. All the weekend’s activities, including lodging, food, tips, and fishing gear rental will be included with the ticket price.

Spots are limited to only 11 folks so grab a ticket now!

Still thinking about it?

Your fellow Owners had a blast last year. Here's what they had to say:


“Amazing experience. The whole event was well planned and executed and I had a great time with my son and with the fellow owners. Will definitely plan on doing it again.”

- Eric F.


“No detail too small. Just like [their] watches, the Oak & Oscar Driftless trip was well thought out with elite extras that only a company would think about. Go ahead and take my money for the next trip.”

- Derek D.


“Amazing trip. If you ever have the opportunity to do a trip with Oak and Oscar, just do it! Great guys, great activities, and great watches.”

- Tony T.

Watch the video
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One of my favorite video's we've ever made....

Check it out and you'll quickly see why. It was such a fun trip and was an honor to have so many great Owners join us!

Click here to watch the video!