We’ve heard y’all, loud and clear, and have added a third night to the annual Built to Discover trip! This means more time to properly unwind and truly escape from the grind of daily life amongst the beautiful scenery of the Red Clover Ranch and good friends.

And yes, we did say more fishing! We added an option for a second guided fishing trip on Saturday afternoon. So if you’re hankering for more time on the water with a professional guide, we’ve got you covered!

Also new this year, golf! Yes, as you have probably noticed, the entire Oak & Oscar team has gotten pretty deep into golf. The great news is, there are several local courses we can play on!

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 Thursday, September 10th to Sunday the 13th for an all-inclusive weekend of fly fishing, bourbon drinking, farm-to-table dining, and an overall awesome time.

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 Thursday evening, we will host a casting class and demo held by a local guide. And on Friday morning, we’ll have the top fly fishing guides in the area showing us the way.

New this year: there will be an optional second guided trip on Saturday afternoon.

And for all the more experienced anglers, there will be additional time, both morning and afternoon, to get out on the water with your own gear!

While fly fishing may be what first brought us to the Driftless, it's certainly not the only way to enjoy this incredible corner of Wisconsin. This year, we're excited to offer two optional golf excursions for those looking to explore even more of what the region has to offer. Whether you're a scratch golfer or simply enjoy an excuse to spend a few hours outdoors with good friends, these outings are a great way to experience another side of the Driftless landscape.

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.

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.

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 so grab a ticket now!

Excited about the extra fishing option? Planning to bring your golf clubs and try your hand at some fantastic local courses? Here’s where you can add those option activities to your weekend.

“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.

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!