The Good Land: Bike Tour to Milwaukee 2024

Fri May 17 2024 at 07:00 am to Sun May 19 2024 at 04:30 pm UTC-05:00

The Perfect Cup | Chicago

Out Our Front Door
Publisher/HostOut Our Front Door
The Good Land: Bike Tour to Milwaukee 2024
A Weekend Bikepacking trip From Chicago to Milwaukee, with a Campground Ho'down and Bike Bar Crawl
About this Event
EVENT DETAILSA Weekend Bikepacking trip From Chicago to Milwaukee, with a Campground Ho'down and Bike Bar Crawl in Milwaukee


Day 1: 80 mile ride | Day 2: 20 mile ride to Milwaukee, 10 miles-ish in Milwaukee, and 20 miles back to camp in Racine, WI | Day 3: 80 miles to Chicago (options to take a train)

Support: Self-supported - you carry your own gear. No vehicle support.

Meals: Some meals are included.

Lunch stop on Day 1: Likely Golosinas El Encanto in Waukegan.

Lunch stop on Day 2: Group to pick from assorted breweries & bars in Milwaukee.

Lunch stop on Day 3: TBD

Transportation: Our starting point is accessible via street parking, CTA Brown Line and near LSD bike route.


Pace: Casual, option to ride together as a group. 12-15mph. Intermediate level.

Trail/Route: Paved road with minimal gravel incorporated.

Lodging: Tent (camping gear not provided). We will stay at Cliffside Campground (Racine County) located 7320 Michna Rd, Racine, WI 53402 (map).


In 2024, we are mixing it up a bit for this ride. The train has consistently been a hassle, and we’ve even had to get a Uhaul to bring bikes back over the last few years. Plus, this ride is so fun, we want to welcome a few more folks along for the ride and really make the most of our time up in our favorite neighboring city. So this time around, we will leave with a crew from Chicago on Friday morning, bike 80 miles to Racine and camp at Cliffside Campground. That is standard to how we usually have run this ride.

But this year, we are going to leave our tents set up at Cliffside, ride 20 miles into Milwaukee to enjoy some food and libations, and ride the 20 or so miles back to Cliffside to camp a second night. Because we have so much love for MKE and its fine citizens (and we just want to ride with them more), we are offering a few free spots for Milwaukee folks to meet the Chicago crew when we arrive in MKE on Saturday. The MKE folks can then come back and camp a night with us at Cliffside.

On Sunday, we will get up, and the MKE folks will be on their own to ride back home, and the CHI crew will ride back to Chicago with options for folks to hop the train 35 miles into the ride in Waukegan. Otherwise, we will be riding the full 80 miles back to our original start point in Chicago.

Read more about the 2023 adventure in this blog post.

Transfers: We have limitations for ticket transfers but may accommodate in the event certain criteria are met. You may review this updated Transfer Policy flowsheet to determine what next steps you need to take.

Breweries/Bars to tour/visit:


Required Items:

Your bike!

Helmet - encouraged but not required

Tent & Camping Gear

Head Lamp

Cash/Debit/Credit Card for your food and your drinks

Photo I.D. and Emergency Contact Info

Two spare inner tubes and tools to replace a flat (guides will be able to assist)

At least 2 water bottles

Bike lights, front and rear

Lock for your bike

High energy snacks

Change of clothes, including swimsuit and/or rain gear!

Phone battery pack

Camp mug, plate/bowl, eating utensils

Welcoming, adventurous, can-do attitude


Campground fees (sites, firewood, etc.)

Dinner on Day 1. Breakfast on Day 2 and Day 3.

Education about our local history and nature

Really nice and supportive guides


Food for Day 1 lunch and Day 2 lunch and dinner (we will stop at designated restaurants for food, but the guides will not pay for these meals)



Our guides are part of a community of volunteers that believe in adventure and helping others find adventure right out our front door. They exude a welcoming, supportive, and inclusive spirit which are foundational values at OOFD. They have love and appreciation for their home and like sharing knowledge about that home with others, thus helping the riders to develop a stronger sense of gratitude for our local history and nature.

The guides will be set with the route and an extensive script about the area you’ll be riding through (a script they may have researched, written, and developed themselves)! They have set up multiple breakpoints along the way to ensure you can go the distance. So if this is your first time out on a long ride, you’ll be surprised by how far you can actually go. They will stick with you and if for any reason you must end the ride early, they will help direct you to the nearest train and way to return to the city.

They will have the tools necessary for most maintenance issues that might arise on a weekend bike camping trip. Our guides will help you with any needed repairs. *If you have your own tools or supplies, especially any that are very unique to your bike, please bring them along. Though guides will have extra tubes and patches, you most definitely should bring at least 2 extra tubes for your bike.

Keep it light and keep it tight!

Secure your belongings and keep highly used items like snacks, rain gear and extra layers accessible when packing. Keeping it light usually makes for a more enjoyable ride; So leave the kitchen sink at home. Avoid dangling straps, they can get entangled in the wheels and cause an accident; Be smart and think about your safety.

Other Stuff To Bring

You might want to bring ibuprofen, comfortable cycling gloves, sunglasses, sunscreen, lip balm and cool information you would like to share.


Dress for the season and in layers. In the spring and fall, outside temperatures at times may be great to wear a T-shirt but when biking, the wind can make your chest, hands, and fingers cold and the weather may change without notice. Bring a pair of gloves and a sweater/windbreaker if need be. If a little rain is in the forecast, bring a rain jacket. Don’t be afraid of the rain!!! Some of the best views are when a storm is on the horizon. If it gets intense, there are shelters along the way to wait it out.

What kind of bike do I need?

All bikes are welcome! On most rides, the routes are mixed terrain ranging from paved road to limestone and gravel; super skinny tires aren’t ideal but we’ve seen them work. A bike rack or other systems to keep your gear off of your back/shoulder is a great idea, though if that is how you roll, no worries, though we strongly advocate riding without a backpack, at least on our longer rides.

Do you rent bicycles out to the public?

We do not.

What if I get tired?

We champion perseverance. Our guides will support and encourage you to push on because the reward of completion is great. In the event of injury, major bike failure or just not being able to push on, the guides will help direct you to the easiest way to return home (usually via Metra or other forms of public trans). Very few of our rides provide van support and if the ride does provide it, it will be explicitly mentioned in the ride description. However, this vehicle should not be relied upon for mere fatigue. There are limited seats.

What happens if it rains? Is the event cancelled?

No, we ride rain or shine. Some of the best views are after a rainstorm. Your safety is our top priority, so if there is severe weather we will break and seek appropriate shelter along the route, then continue on to our destination.

How fast do you ride?

General rule of thumb is a steady 12 miles per hour, though some of our advanced longer distance rides the pace will vary from 12 to 18 mph. On shorter beginner rides, as well as Family and Youth rides, the pace can be as low as 8-10 mph.

What happens if I'm too slow or too fast?

On most rides, we do our best to ride together as a group. Separation in the group can occur, but we do not leave anybody behind. A guide will always be riding at the back and at the front (and usually at least one floating in the middle). This is not a race, so everyone will do their best to keep the pace of the lead guide and should not plan to ride faster than the lead guide. In the case that a rider is consistently falling significantly behind the rest of the group, a guide may consult with that participant and advise on an alternate method to reach camp or home. This is always a last resort, and rarely happens, but if that participant and their accompanying guide are likely to arrive at camp hours after the rest of the group, those suggestions may arise.

What happens if my bike breaks?

First, always bring two spare inner tubes. Our Guides carry extra tools and supplies, are always ready to help and are trained for emergency repairs. We are usually too far from a bike shop in case anything major happens. Although, if a roadside repair is not possible, then a trek to the nearest Metra Station or best mode of public transportation may be the best option (we’ve even had folks call a friend or an Uber).


Participant Cancellation: No Refunds. | By registering, you acknowledge and agree there will not be a refund if you cancel or do not show up for the event. Tickets cannot be resold. We are a small organization and due to the small group size of our rides, a ticket cancellation or no show has a real impact on the planning of the tour. As such, we cannot provide any refunds for a participant's cancellation. Please contact the ride organizer if you are no longer able to attend.

Organizer Cancellation: Full Refund | Nobody wants an event to be canceled. In the rare circumstance the organizer cancels the event at their discretion, registered participants will receive a full refund.To date, this organization has canceled minimal events; primarily in response to the Covid19 pandemic.

Weather and Rain: We do not cancel an event for rain, storm, or any other weather. We ride rain or shine. Chicago weather is typically passing, if the weather requires, we will pause the ride and wait in a sheltered space then continue biking.Some of the best views of the lake and greenery on the trails are after a rainstorm.

Inclusivity and Non-Discrimination Statement (included in the Waiver)

We at Out Our Front Door believe in the radical inclusion of all people on our bike camping trips. Regardless of your race, gender identity, sexual orientation, economic status, or even the types of bikes you ride, we want you rollin’ with us. We want everyone to feel welcome. As a participant of an Out Our Front Door event, you are inherently agreeing to Ride and Let Ride.

If you exhibit any micro-aggressions observed by leaders, such as being judgmental of another’s bike, touring experience/skill, mansplaining, or generally being unfriendly you will be politely yet firmly corrected by OOFD leaders. If you commit any serious offense such as repeated unwanted flirtation, sexual harassment, overt racism, etc., you will be asked to leave the tour without a refund and will no longer be welcomed on future rides.

If you feel you are a victim of any of the above or have observed it, please raise the issue with one of our ride leaders, and they will handle the issue accordingly and with appropriate discretion.

We have this policy in place because we want everyone to feel safe and welcome. Out Our Front Door is an open community of bike campers, and we will forever work to bring all sorts of folks into the fold. Thank you for being a positive contributor to that community.


We're the Out Our Front Door Organization. A bike camping community for Chicagoland.

See Our Full Schedule Of Events Here

As a community organization, Out Our Front Door’s mission is to immerse, educate, and preserve the history, culture, trails, and native habitats of the Lower Lake Michigan Basin Area through exploratory adventures. Established in 2015 with the North Loop Ride, we now have many different resources, events, and programs ​we offer the public.

Drop us a friendly visit at: ​ Facebook | Instagram |


Event Venue & Nearby Stays

The Perfect Cup, 4700 N Damen Ave, Chicago, United States


USD 115.00

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