Back and finally recovered from my annual jaunt to the Driftless Area, it’s time to journal some of the goings on for posterity’s sake. Now, I could write a MegaPost™ similar to 2023’s version, but instead will opt for more palatable smaller bites.
I’ll begin these entries with my arrival in the Driftless, on Friday May 23rd. My flight from Jacksonville to Minneapolis was very early in the morning. So early that I actually chose not to go to bed the night before. The lack of sleep made the both flights, with a connection through Atlanta, quite forgettable as I dozed off through the large majority of each. The plane pulling away from the gate served as a signal to close my eyes.

The drive from Minneapolis to Westby, Wisconsin is an easy two and a half hour cruise down a few highways with only a handful of turns and exits. The urban landscape surrounding the airport quickly gives way to rolling hills, pastures, and farmland. Early Spring weather had taken over as green grasses and densely leaved trees were omnipresent. My friends and I often refer to the Driftless as “The Shire”, as stolen from Hobbit lore, and it was certainly living up to that moniker.
The comfort of the rental car, a brand new and honestly too well appointed Subaru Outback (with only 5 prior miles on the odometer) made the drive a pleasure. Arriving at my destination, I was now officially in a stress-free zone.

I was staying with two friends, Anthony & Matt, in a VRBO house rented for the week right alongside Timber Coulee, a well known Wisconsin Driftless trout stream. As a matter of fact, a fork of Timber ran right through our backyard! We were all targeting arriving at the house around the same time, Anthony driving in from Pittsburgh and Matt staying the night at a local campsite. I just so happened to arrive first.

Despite the high afternoon sun and bluebird skies, I was not one to waste an opportunity to get a line wet as soon as possible. With a stream in the backyard and nobody else there yet, unpacking could wait! After unfurling my tenkara rod a few fish obliged as I worked my flies through some shady spots. The “skunk” (and any associated pressure) was off the trip by just the second cast.

No more than ten minutes later Anthony seemingly materialized in the driveway. Collapsing the tenkara rod and spooling up the line, I scaled the short grass berm to help unpack the cars and move into the house for the week. Matt arrived shortly thereafter and the three of us chatted for a bit, catching up on lost time. It had been a while since last we were all physically in the same place.
The house was a real gem. Named the “Timber Creek Retreat”, almost every nook and cranny was decorated in a tasteful trout motif. Wall art here, bath towels there, fly fishing books strewn across the coffee table, it’s how I’d envision my house looking if I lived somewhere closer to cold water streams holding trout.


After relaxing a bit from our travels on the comfy living room furnture, we found dusk had snuck up upon us. Matt was going to run back to the campground for one final night, so Anthony & I decided to fish a different section of nearby stream for a few hours before it got too dark.

Upon arrival, we quickly noticed a small caddis hatch to which the resident brown trout were popping in the deep pools. Like aquatic gymnasts, several catapulted completely up and out of the water in an attempt for a quick meal.
Anthony & I chose to split up a bit, although fished within sight of each other. Taking the cue from the porpoising fish, I caught my first on a dry fly, a size 16 elk hair caddis (ECH), and continued to catch quite a few more of similar size and shape as I followed the water’s upstream meander.

Occasional glances back toward Anthony revealed several instances of him standing with rod bent deeply, he was clearly picking up fish as well.

There’s a particular section of this stream that has a bit of a drop-off with a pool and run that is deeper than most. Wanting to “get down”, I snipped off the now mangled EHC and tied on a Pink Squirrel kebari, a “tenkara-ized” version of the famous beadhead nymph that is considered by many to be the most prolific fish catching pattern of the Driftless region.
A few short drifts summoned some flashes and strikes, but nothing firm. The fish were there, I just couldn’t get them to commit. A follow up cast and drift toward the back corner of the pool sent an unexpected bolt of lightning up my line. There was now a fish on, and it was heavy! Feeling the deep bend, whatever was on the end was either big or foul hooked. After a few runs up and down the watery course the brown trout revealed itself to be the former.

Once sufficiently tired and brought into the shallow to be netted, I found the full-bodied brown trout to be almost the length of my net bag, nose to tail. I don’t really measure fish, but I’d put it somewhere in the 16-17″ range. Possibly the largest trout I’ve ever caught in the Driftless, certainly the coolest looking. The micro kype at the end of its lower jaw protruded just enough to make that mug memorable.




After letting the fish glide back into the depths and allowing the adrenaline to work its way through my system, Anthony & I met up a bit later on stream. The sun had just about set by this time so we both considered our time done. He revealed that he had in fact had a great night working dry flies over countless fish. I was thrilled to hear about his success, validating this quick run to the stream for the both of us.
At this point we were both hungry, so we decided to head into town for a bite to eat. As we entered Legacy, a local bar & grill type of establishment we’ve visited many times, the waitress gave us a friendly warning… “Our restaurant was sold and is closing at the end of the month, so we’re selling down the food. No steaks, no mayonnaise, no iced tea…” She mentioned a few other unorderables before Anthony & I both decided on fried fish sandwiches. Fried fish on a Friday felt like a very Midwest thing to do.

Sitting at a corner table, we closed out our first night in the Driftless exchanging stories of fishing & family while also making some plans for the next morning’s outing in between bites of perfectly crisped sandwich. So much had already happened in just a few short hours, but we could both feel that so much more lay in the days ahead.

Entries to the Driftless 2025 series:

Michael
Your adventure here on the Driftless is the closest I will ever come to fishing in this place. I will be following each post—thanks for sharing