Day 0 – Friday, June 26: Sauk City
Sauk City sits along the Wisconsin River at the edge of the Driftless region, a gateway town known for its relaxed riverfront, easy access to quiet country roads, and proximity to some of southern Wisconsin’s most scenic riding. It’s an inviting, easygoing place to begin our tour.
Spend the afternoon exploring:
- Walk the riverfront or ride the paved Great Sauk Trail, where sculptures and statues pop up when you least expect them.
- Visit the Sauk Prairie State Recreation Area for wide‑open prairie and birdwatching.
- Settle in at Wollersheim Winery—one of Wisconsin’s most celebrated destinations—for tastings, vineyard strolls, cellar history, and a terrace overlooking the river valley.
- Take a short drive to nearby highlights such as New Life Lavender & Cherry Farm, where the Lavender Festival is underway, or Spring Green’s attractions, including Taliesin, the American Players Theatre, and the House on the Rock.
In the evening, meet your fellow riders, pick up your packet, and enjoy dinner together as we get ready for five days of great riding.
Day 1 – Saturday, June 27: Sauk City – New Glarus
57 miles; 2,376 feet of climb
Quiet back roads and rolling scenery set the tone for today’s ride. We’ll make our way to Mount Horeb—the Troll Capital of the World and one of Wisconsin’s most charming small towns—where carved trolls, local shops, and eateries (including the Grumpy Troll Brew Pub) line Main Street. We’ll also stop at a working dairy farm for a tour and a look at modern dairy practices; past riders have even witnessed a calf being born.
Once in New Glarus, our home for the next two nights, you’ll discover why it’s often praised as one of Wisconsin’s most distinctive and welcoming small towns. You can visit New Glarus Brewing Co. for a self‑guided tour and fresh samples on the outdoor patio, explore the Swiss Historical Village’s 14 artifact‑filled buildings, or stroll downtown to find all 15 painted cows and enjoy the bakery, chocolate shop, winery, and meat market.
In the evening, enjoy Swiss entertainment and a festive dinner with your fellow riders.
Day 2 – Sunday, June 28: New Glarus – New Glarus
0–63 miles
44 miles; 1,413 feet of climb
63 miles; 1,837 feet of climb
Today’s loop ride winds through scenic pastoral stretches with plenty of opportunities for coffee, pie, ice cream, and small‑town eateries along the way. Ride as much—or as little—as you like.
Afterward (or instead of riding), enjoy more time exploring New Glarus, a perennial favorite among past participants for its friendly atmosphere, walkable downtown, and one‑of‑a‑kind character. We’ll gather for a group happy hour, and dinner is on your own, but we’ll be organizing optional small‑group dinners for those who’d like to join others.
Day 3 – Monday, June 29: New Glarus – Madison
58 miles; 1,978 feet of climb
Today’s route continues through scenic, pastoral countryside. We’re in cheese country, so it’s only fitting that we stop at a cheese factory to sample their specialties. We’ll also visit a hops farm to see where local breweries source their hops before riding through the charming village of Paoli, which sits along the Sugar River and is a favorite stop for area cyclists. Later, tour a dairy plant to learn about milk bottling, cheese making, and ice cream production. Treat yourself to one of their 25+ flavors, including Badger Blast, Union Utopia, and Mocha Macchiato.
You can also stop at the free Vilas Zoo to see 200+ animals and enjoy more locally made ice cream.
Our destination is Madison—consistently ranked among the best places to live, bike, and eat in the country. With its vibrant downtown, award‑winning food scene, and nationally recognized cycling infrastructure, Madison offers the perfect blend of big‑city energy and small‑town friendliness.
Our hotel is steps from State Street, with endless eateries, brewpubs, and shops. Join the group for happy hour, then enjoy dinner on your own in this foodie paradise.
Day 4 – Tuesday, June 30: Madison – Madison
62 miles; 1,782 feet of climb
45 miles; 1,324 feet of climb
No need to pack your bags—today is a loop ride. We’ll head out through gently rolling countryside as the terrain flattens a bit, passing pastoral farmland, peaceful rural roads, and scenic stretches alongside area lakes. Along the way, you’ll find plenty of options for refueling, including coffee shops, cafés, and great mid-ride stops.
Riders looking for shorter options (15–20 miles) can enjoy local trails offering paved paths and scenic lake views.
After—or instead of—your ride, explore Madison:
- Relax at a nearby beach or rent a SUP, kayak, or canoe.
- Tour the Wisconsin State Capitol with its handcrafted furniture, mosaics, and granite dome.
- Wander the 16 acres of Olbrich Botanical Gardens, voted one of the most inspiring gardens in North America.
- Visit museums such as the Wisconsin Historical Museum, Veterans Museum, Madison Museum of Contemporary Art, or the Chazen Museum of Art.
- Explore State Street, the Capitol Square, and Memorial Union on the UW-Madison campus – a well-known gathering place on Lake Mendota.
We’ll gather for happy hour and enjoy our final dinner together.
Day 5 – Wednesday, July 1: Madison – Sauk City
52 miles; 2,171 feet of climb
Our final route takes us across the Wisconsin River via the Merrimac Ferry—one of Wisconsin’s most beloved and historic crossings. Grab an ice cream cone for the ride, then finish the tour on the Great Sauk State Trail as we make our way back to Sauk City. Showers will be available at the end.
Routes are subject to change.