There is no better way to celebrate the crisp, golden promise of autumn than with a road trip winding through the heart of the Midwest. For lovers of architecture, history, and the gentle thrill of discovery, the 2025 Fall Trip to Taliesin is a journey not to be missed. This thoughtfully planned weekend—from October 11th to 12th—will carry us from the rolling farmlands of Illinois to the storied landscapes of southwestern Wisconsin, blending iconic design, local flavors, and the nostalgic beauty of classic cars beneath a canopy of fall color.
Itinerary Overview
- Saturday, October 11th: Departure from Hampshire, Illinois; brunch in Paoli; tour of Frank Lloyd Wright’s Taliesin; overnight at the Round Barn Lodge; dinner at a classic Wisconsin supper club.
- Sunday, October 12th: Visit to the Midwest MicroCar & Cycle Museum; lunch and farewell at Bailey’s Run Vineyard & Winery.
Saturday: Setting Out on the Road
Our meeting point is the McDonald’s at 19 N 649 US-20, Hampshire, IL 60140—strategically located near the intersection of routes 90 and 20. At about 9:00 AM, our engines will rumble to life, and our caravan will set forth. The first leg is a two-hour, 95-mile journey northward, an easy pace that allows us to relax and soak in the transformation of the landscape. October in the Midwest brings a painter’s palette to the trees—maples flare red and gold, oaks smolder bronze, and the fields await the quiet of winter.
Brunch in Paoli: Seven Acre Dairy Company
By 11:30 AM, we will roll into the charming village of Paoli, Wisconsin. Our destination: the Seven Acre Dairy Company, a historic creamery that has been lovingly revived as a destination for food lovers and explorers alike. Here we’ll enjoy a leisurely brunch. Whether you opt for warm pastries, farm-fresh eggs, a hamburger, or a strong cup of locally roasted coffee, there’s something for every palate.
There is time also, to explore the grounds—wander the riverside path, browse artisan wares, or simply enjoy the scent of autumn leaves. At 1:00 PM, we will regroup, ready for the next chapter.
Drive to Taliesin: The House on the Hill
The road to Taliesin is a scenic, hour-long drive of 50 miles. As the hills grow more pronounced and stone bluffs punctuate the horizon, anticipation mounts. Taliesin itself sits just outside Spring Green, perched above the Wisconsin River with views of meadows and forest that inspired Frank Lloyd Wright throughout his extraordinary career. Our guided tour is scheduled for 2:45 PM. This is more than a house; Taliesin is a living testament to Wright’s vision—his “autobiography in wood and stone.” The tour takes us through the main residence, drafting studio, and gardens, with knowledgeable guides illuminating tales of innovation, tragedy, and triumph.
Saturday Night: Wisconsin Hospitality
As the sun dips toward the horizon, we make our way to the Round Barn Lodge. This welcoming inn, with its rustic charm and echoes of rural Wisconsin, is the perfect place to unwind. The Illinois Jaguar Club has a room block for Saturday night. Rate is $145 and reservations must be made over the phone, 603-588-8568, mention the Illinois Jaguar Club. Reservations must be made by September 11th. Please make reservations early, as rooms are limited.
Dinner at Arthur’s Supper Club
No visit to Wisconsin is complete without experiencing the supper club tradition: hearty fare, convivial atmosphere, and perhaps a classic brandy Old Fashioned to toast new memories. The menu is sure to please, whether you crave prime rib, fresh-caught fish, or the comfort of a well-prepared supper in the company of friends.
Sunday: Wheels, Vineyards, and Farewell
At 9:30 we will drive a short 15 miles (about 30 minutes) to the Midwest MicroCar & Cycle Museum. Even if you haven’t yet fallen for the quirky charms of these tiny autos, you’ll find yourself captivated by their ingenuity and character.
Midwest MicroCar & Cycle Museum
The museum is a treasure trove of automotive history. Here, every car has a story: from postwar European microcars to rare cycles that once zipped along narrow city streets. The collection offers a glimpse into a world where efficiency, creativity, and whimsy went hand in hand. For enthusiasts and the merely curious alike, it’s a delightful stop.
Lunch at Bailey’s Run Vineyard & Winery
Our final destination is Bailey’s Run Vineyard & Winery, a picturesque spot 40 miles (about an hour) from the museum. By midday, we’ll arrive amidst rows of grapevines and rolling hills. Lunch here is a relaxed affair—savor local wines, sample artisanal cheeses, Neapolitan brick oven pizza, small plates, and bask in the honeyed sunlight of an autumn afternoon. It’s a fitting close: nourishment for body and spirit, and a chance to raise a glass to the journey we’ve shared.
Practical Tips and Final Thoughts
- Pack for the Weather: October in the Midwest can be unpredictable—layers, a rain jacket, and sturdy walking shoes are recommended.
- Take pictures: Whether capturing the architectural lines of Taliesin or the flame-red maples of Wisconsin, you’ll want to remember these sights.
- The best journeys are those where you allow yourself to be surprised. Embrace new experiences, new friends, and the quiet magic of the season.
As we return from the fields and forests of Wisconsin, we will carry home more than souvenirs. This trip is an invitation—to see anew, to connect, and to celebrate the enduring legacies of art, ingenuity, and community. Here’s to the 2025 Fall Trip to Taliesin: a weekend to remember, and a story to tell for seasons to come.
$60 Payment includes admission to Taliesin and the Midwest MicroCar Museum. Meals and lodging are not included.