Fully supported, affordable Wisconsin Hotel Bicycle Vacations & Florida Keys Bike Ride
Old World Wisconsin Itinerary 2027
Friday June 4: Afternoon Warm up Ride around Madison
12 Miles
A town of dual capital roles----Wisconsin’s State Capital and Capital of cycling. Expect to be riding on a scenic paved bike path along a lake shore, through a park, on a quiet street, or a wide bike lane. It won’t take long to realize you are biking through a model for the rest of the country to follow. Our loop ride for the afternoon begins and ends at the paved Capital City Trail, right at the hotel front door.
No matter what your destination, you can get there safely by bike in Madison. And at the end of the ride there are dinner choices nearby for any desire, followed by time to meet other riders and hear how easy it will be to find ice cream in the week ahead.
Spark by Hilton (new hotel) is the ideal place to begin and end our tour. Pool, workout room, and miles of paved bike path at the door.
In the morning leave your car in the parking lot, put your bags on the truck, and get on your bike for a week of outstanding cycling!
Saturday June 5: Madison to Whitewater 52 miles
It's always nice to leave the car behind, put your bags on the truck and get on your bike. That's all you have to do to start on your way as we exit Madison on Saturday morning. Taking advantage of how much Madison has done for cycling leaving town is scenic and simple. A beautiful local bike path through forests and lakes helps us exit Madison nearly traffic-free!
We suddenly find ourselves in the heart of America's dairyland, a Northwest tailwind pushing us quickly towards Whitewater, Home of University of Wisconsin at Whitewater. A small school, it's not to be confused with U of W--Madison. On the way there are some great food choices in Ft. Atkinson where you can find more energy than needed to propel you past the nearby grazing cows. As we near Whitewater a network of scenic back roads brings us to Baymont Inn and PAW Social Hours the next two nights.
Longtime PAW Alums will recall the first tour in PAW's history going to Whitewater in 1985. It was the first of many years of anticipated weekends. This is one of those areas that has not changed much over the years, in short, an area still great to cycle. A place where the glacier was just friendly enough to come to a halt after arranging the curve of the earth so as to be bike friendly.
Now it's your turn to ride this blend of dairyland roads mixed with gently rolling rustic byways. The route is arranged in a loop to offer choice of miles for those who want extra time in the pool, hiking on the Ice Age Trail, or browsing in town.
Whitewater is home to University of Wisconsin- Whitewater, and has a variety of places to eat and drink plus two good bike shops.
Sunday June 6: Kettle Moraine Whitewater Lake Recreational Area
Scenic loop options: 35, 40 or 50 Miles
Monday June 7: Whitewater to New Glarus 55 miles
Excitement builds as we head for the well known town of New Glarus. Founded in 1845, New Glarus was named after Canton of Glarus in Switzerland. In the early 1840's when failed crops created poverty in Glarus, 193 residents left for the New World seeking better times. They found their way to Wisconsin and bought two square miles of land along the little Sugar River for $1.25 an acre because the valley with its surrounding hilltops reminded them of home. Today, Swiss architecture abounds in New Glarus which has become known as "America's Little Switzerland." The town has many interesting places of Swiss origin to visit, has specialty shops and good restaurants and is surrounded by both beauty and scenic back roads to bike.
Our home tonight is the Chalet Landhaus, a prominent New Glarus Swiss style landmark that fits perfectly with the character of New Glarus. Even better, our upgraded hot breakfast buffet cooked fresh daily on site is included all 3 mornings, so you'll have a great breakfast waiting for you before heading out for the day's ride.
Group Dinner tonight right at Chalet Landhaus Hotel! Shortly after our Happy Hour featuring Spotted Cow beer of course.
Tuesday June 8: New Glarus Layover: 36 or 50 miles
3 Nights in New Glarus!
Today's ride takes us from Chalet Landhaus to the wonderful town of Mount Horeb and back, with an optional extra-mile loop through the beautiful valley just north of town.
Enjoy quiet country roads, rolling farmland, open valleys and classic Wisconsin scenery along the way. Once in Mount Horeb, you'll have time to explore this lively, charming community known for its unique shops, great restaurants, Scandinavian heritage and fun small-town atmosphere.
The extra loop north of Mount Horeb adds even more beautiful scenery before we head back to New Glarus. It's a fantastic day of riding with a great destination and plenty to see along the way!
Way back in PAW's 1st year, 1985, New Glarus served as an excellent location for a weekend tour that was well attended for about 20 years. Today, we are excited to have 3 nights in scenic & historic New Glarus on Old World Wisconsin. Our layover route features mileage options which include choice roads from our original routes. The area today remains unspoiled and lightly traveled, just like back in 1985. Cycle your choice of mileage and still have time to visit the New Glarus Brewery, just 1.5 miles from our hotel easily accessed by bicycle path directly behind hotel, or walk into town which is just around the corner.
Dinner tonight on your own, plenty of excellent choices await in New Glarus!
Wednesday June 9:
New Glarus Layover Loops: 20, 40 or 55 miles
Thursday June 10: New Glarus to Madison: 30 Miles
A GREAT WAY TO END A GREAT TOUR
If a great tour has to end, it’s hard to think of a better place to finish than Madison. Along the way, we’ll enjoy a network of traffic-free bike paths and quiet backroads, riding scenic country roads that are well known to local cyclists. It’s an easy, beautiful ride into Madison and a wonderful way to wrap up the tour.
And as the saying goes, PAW tours never really end...the memories last forever!
Arrival in Madison offers a variety of choices, all of them good. See some of Madison you missed before the tour, return to a good lunch spot, or stay over and enjoy an extra day. Those who have to leave will find their highway right at the door.
"PAW does it again! Superb scenery with gorgeous lakes, forests, and wildlife to enjoy. Very little traffic and good roads. Dr. J. has found roads even we from Wisconsin have not ridden on. Thanks to Dr. J. and his excellent crew for a perfect vacation." Mary Ann Duckert- Waukesha WI.
Ice-cream buffet..you know you're on a PAW trip.
Kettle-Moraine Whitewater Lakes and recreation area.
Madison Wisconsin--Beautiful riding around Lake Mendota
Traffic-free backroads are waiting!
Enjoying a terrific group dinner & making new cycling friends.
Almost back...PAW Social Hour is near!
(All roads on tour are paved)
NEW GLARUS TO MONTICELLO, ALBANY & BRODHEAD
Today’s ride takes us south from Chalet Landhaus through some of the prettiest countryside in southern Wisconsin. Expect quiet country roads, rolling farmland, open valleys and beautiful rural scenery as you make your way toward three charming Wisconsin communities.
🚴 20 miles -Monticello: Our shortest option takes you to Monticello, a friendly small town with a historic downtown and several options for a mid-ride coffee, lunch or sweet treat. It’s a perfect destination for a shorter day of riding.
🚴 40 miles -Albany: This beautiful 40-mile route winds through the rolling hills and peaceful farm country with quiet roads, wide-open views and plenty of classic Wisconsin scenery. In Albany, PAW will have a food stop waiting for you in a local park, giving you a chance to refuel, relax and enjoy some time with fellow riders. On the return trip, you’ll pass back through Monticello, giving you another opportunity to enjoy this charming little town before continuing on to New Glarus. It’s a terrific day of scenic riding, good food and small-town Wisconsin.
🚴 60 miles – Brodhead: The longest option continues all the way to Brodhead, with beautiful countryside, wooded sections and the scenic Sugar River corridor along the way. Brodhead offers several restaurants and taverns, plus the chance to grab an ice cream or other treat before heading back to New Glarus.
Whether you choose 20, 40 or 60 miles, this is a great day to simply ride, explore and enjoy the beautiful backroads of southern Wisconsin. Another Happy Hour featuring New Glarus Brewing company awaits for us back at Chalet Landhaus.