Milwaukee
This weekend vacation to Milwaukee is a vibrant mix of urban excitement and nature. Cycle along the scenic lakefront trail, where you'll discover stunning parks and some of the best riding paths in the area. Arrive to Milwaukee where we will have your hotel and dinner at a local Milwaukee restaurant booked for you. Start the next day with a walking tour through the city’s thriving neighborhoods, each offering its own unique charm—from the historic Third Ward with its chic boutiques and trendy eateries to the lively Brady Street. Return to Chicago by car, carrying with you the memories of Milwaukee’s charm and excitement.
Itinerary
Day 1
Departure
Bikers will be asked to arrive at the meet-up location at 7am on Saturday morning with everything they need for the ride. Check our packing list for more details on what to pack. Riders’ bags will be loaded up into the vehicle while the riders apply sunscreen provided by our team.
Before rolling out, your guide will conduct a morning brief to review the 90 mile route, safety protocols and address any concerns or preferences among the riders.
Rest Stops
A rest stop will be scheduled for every 15 miles, but this increment is often adjusted based on the fatigue of riders, the weather conditions, and the need for any bathroom breaks. The riders have full say of how often rest stops are made to ensure everyone has a comfortable and safe ride.
Landmarks
The group will stop to see the Bahāʾī temple, listed on the National Register of Historic Places and the only Bahāʾī place of worship in North America. The next stop on the ride will be the ‘Home Alone’ house, the location of the famous Christmas film that took place in the Chicago Suburbs.
Lunch
The group will roll into Kenosha where they will go to one of the area's best restaurants, Anna's on the Lake. The team will fill up water and re-apply sunscreen before hopping back on their bikes.
Arrival in Milwaukee
Your bags will be waiting for you at the Hilton Milwaukee hotel, where you can shower and change before dinner. Dinner in Milwaukee promises to be a culinary delight, giving riders a taste of the city’s vibrant food scene.
Day 2
Tour of Milwaukee
After breakfast at the hotel, meet your tour guide who will take you on a tour of Milwaukee’s best attractions and reveal to you all the city’s biggest secrets. You will have plenty of opportunity to chat with your guide and ask questions while you visit the City Hall, Historic Third Ward, and many other sights.
Brunch
Milwaukee is known for its brunch, the group will enjoy some of the city’s best food at Blue’s Egg. The restaurant is known for its delicious take on classic American breakfast and lunch dishes, including eggs benedict and pancakes.
Landmarks
After brunch, the group will have free time to explore some of Milwaukee's unique attractions, including its renowned breweries and captivating museums. Notable spots include the Milwaukee Art Museum, the National Bobblehead Hall of Fame Museum, and the Black Holocaust Museum. The city is also home to over 40 breweries, with iconic names like Schlitz and Pabst leading the way.
Return to Chicago
After lunch, get driven back to Chicago. You'll arrive between 4-5pm on Sunday, and you'll be able to collect your bike and bags from the drop off location.
What to Expect
You'll traverse mostly flat terrain that shifts between suburban areas and secluded bike paths. Expect southward winds along the lake, so be prepared to experience some headwinds during your ride.
This tour is perfect for beginners who enjoy moderate distances and terrain. This start of this route is a great warmup to get you comfortable on the saddle before heading on roads that are more heavily trafficked. When booking, riders will have the ability to select the speed that best fits them. Keep in mind the longer the distance the slower your pace will be able to maintain.
All food and lodging will be included in the trip price. Riders need to come prepared with all necessary gear included in our packing list. Luggage transportation each way and transport of your bike back to Chicago is included. Our support vehicle will be available for any of the circumstances highlighted in our safety packet.
Check out the resources page for frequently asked questions. We also encourage you to reach out with any concerns using our contact form.
Hilton Milwaukee
