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Bikepacking Trip To Milwaukee

Out Our Front Door
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Endorsed by Curators:
May 12 7:00AM - 7:15PM

A Weekend Bikepacking trip From Chicago to Milwaukee and Back. With aBike Bar Crawl in Milwaukee and a Campground Ho'down


Start: Buckingham Fountain, Chicago, IL

Meet: 6:00 am at Buckingham Fountain Sat. morning

Ride to: Milwaukee & Camp Overnight

Return to Chicago by Train. Arriving back at 7:17 pm Sunday evening

Registration comes with Guided Tour, Campsite & more. Bring your tent and camping gear on your bike.

Day 1: 80 Miles |Day 2: 28 miles then Train home

All Are Welcome.


  • Campsite reservation
  • One Return Amtrak Train Ticket
  • Dinner upon arrival and warm breakfast
  • Campfire & S'mores
  • Adult beveragesInterpretative Trail Guides
  • Special Trip Collectible
  • MilwaukeeBar/Brewery Exploration


Milwaukee the good land is a 2 day, 1 night bike camp-out from Chicago to our neighbor to the north Milwaukee, where we will bike to and camp at cliffside park in southeast Wisconsin along beautiful lake Michigan. Enjoy warm campfire and cool beverages in route to a bar-bike crawl in Milwaukee followed by a leisurely train ride back home to our beloved city of Chicago.

Breweries/Bars to tour/visit:

  • Lakefront Brewery
  • Palomino (classic MKE tavern)
  • Wicked Hops Pub
  • Maybe some more (day of decisions)


  • Your bike, Tent, sleeping bag and gear.
  • A Water bottle, high energy snacks, bike lock, spare inner tube, bike lights & a Helemt
  • Personal Items and change of clothes- There are showers at the site so bring your own soap, small towel and deodorant.
  • Cash/Card for Lunch and Drinks: We will be stopping at affordable restaurants along the way for lunch. Note: You are more than welcome to bring your own main meals.


The Tour Guides will have a bike tool kit, an air pump, a presta/schrader valve adapter, tire lever, chain breaker, and a crescent wrench (for those older bikes), a multi-toolkit, lights and emergency packet. Our guides will help you with any needed repairs. *If you have any of the above items please bring them along at your own convenience.

Our Guides have worked with historians, biologists, forest rangers, and leading people in their fields to deliver a one kind trip. They have setup multiple break points along the way in all the right places to ensure you can go the distance. So if this is your first time out on a long ride Youll be surprised on far you can actually go.


Bike rack

  • We suggest to purchase a back rack if you do not have one already. A bike back rack will improve this trip and any future riding you do on your own. A bike rack will also keep the weight off your shoulders. Stop in your local bike shop to help get your bike geared up.

Keep it light and keep it tight!

  • Secure your belongings and keep highly used items accessible when packing. Light weight usually makes for a more enjoyable ride; So dont bring your living room furniture on the ride. And Avoid dangling straps, they can get entangled in the wheels and cause an accident; Be smart and protect your safety.

Other stuff

  • You might want to bring, a photo device, pain relievers, comfortable cushion bike gloves, sunglasses, sunscreen, lip balm, information to share.


  • Bring some swim wear we might go for a quick dip in the lake. Dress for the season, during spring and fall make sure to bring gloves for your hands and layer your clothing. Even when the weather is nice, when riding your bike the wind can make you chilly really quick.If a little rain is in the forecast bring a rain jacket. Dont be afraid of the rain!!! Some the best views is when a storm is on the horizon. If it gets intense there are shelters along the way to sit it out for the moment.


Can anyone ride this trip?

  • Yes! It is a challenge. Just about anyone who has ridden a bike for a day can do the tour. You should build up your riding distance/endurance to at least 50 miles. Not sure you can ride it? Check out our website

What kind of bike do I need?

  • It's really up to you. But we recommend a Touring, Road, Urban or Hybrid bike. These types of bikes make for a more comfortable ride. Attaching a bike rack will help carry your daily supplies and keep weight off your shoulders.

What type of trails do you ride?

  • The trails on Day 1 are mostly paved bike paths and very little counrty roads. Day 2 trail conditions range from group road riding, single trek, and paved bike paths.

Do you rent bicycles out to the public?

  • At the moment no

What if I get tired?

  • We champion perseverance and the challenge. We encourage to push on, the reward of completion is great. But if turning around is an absolute must, there is always a train station relatively close by throughout the entirety of the tours.

What should I bring for the bike trip?

  • Always bring a spare inner tube. Dress for the season. During spring and fall make sure to bring gloves for your hands and layer your clothing. Even when the weather is nice, when riding your bike the wind can make you chilly really quick.

What happens if it rains, is the event cancelled?

  • No. We still ride if there is rain. Some of the best views are after a rain storm. Though safety is our top priority. So if there is extreme severe weather we will break and wait it out in a provided shelter, then continue to our destination.

How fast do you Ride? What is the pace of your tours?

  • The pace we ride at is around 12-15 miles per hour. This is to accommodate everyone riding the tour and to be able to take in all the views.

What happens if I'm too slow? What happens if I'm too Fast?

  • We ride together as a group. We do not leave anybody behind. A guide will always be riding at the back and at the front.

What happens if my bike breaks?

  • First, always bring a spare inner tube. Our prepared Guides are always ready to help, are trained for emergency repairs, and carry extra tools and supplies.


Individual/Participant Cancellations: No Refunds | We are a small organization and due to the small group size of our rides, a ticket cancellation/no show has a real impact into the planning of the tour and as such, we cannot provide any refunds for a participant cancellation. By registering you acknowledge and agree there will not be a refund if you cancel or do not show up for the event.

Organizer Cancellation: Full Refund | Nobody wants an event to be cancelled. But in the very rare case the organizer does cancel the event at their discretion due to unforeseen circumstances, then registered participants will receive a full refund. To date this organizer has never cancelled an event.

Weather and Rain: We do not cancel an event for rain or a storm. We ride rain or shine. Understand that Chicago weather is typically passing, if it gets intense we will wait it out in a provided shelter then continue biking. FYI-Some of the best views and greenery are after a rain storm.


We're the Out Our Front Door Organization. A Chicago Bike Camp Collective

See Our Full Schedule Of Events Here

We provide online resources and exploratory adventures by immersing and educating in the history, culture and the uniquely beautiful natural habitats of the Lower Lake Michigan Basin Area, including Illinois, Wisconsin, Indiana, and Michigan.


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