American Heartland Tour

Witness the Revitalization of the Rust Belt

In 2022, I did a Bitcoin Tour of America on my Harley, stopping at over 30 Bitcoin meetups as I criss-crossed the nation on backroads. The Midwest was one area which exceeded my expectations in every way. Not only for the beauty of the cities and the landscapes, but the loyal and hardworking people who are renewing this land and its history.

A woman sitting on a black and orange Harley-Davidson motorcycle outside a museum with a large Harley-Davidson sign on the building. She is smiling and wearing a denim jacket, jeans, boots, and a baseball cap.

This Ride of Passage will allow you to participate in this revitalization and build connections with the ranchers, Bitcoiners and entrepreneurs making change here. Experience the lifestyle of a sovereign individual as you cruise across the prairies on the ultimate freedom machine.

It’s time to stop asking for permission and seeking convenience: we have a nation to save.

Who is this Ride of Passage For?

The Ride of Passage: American Heartland Tour is for those of you looking for a way out of a seemingly dead end. The great men and women of the Midwest are creating their own opportunities - you’re going to learn from them through this journey.

Three men standing side by side with their arms around each other in front of a brick building, with a Harley-Davidson motorcycle in front of them. One of the men is holding a drink, and they are smiling.

We’ve planned every stop and experience for you, so you can focus on participating wholly in this adventure: from shaking hands at Bitcoin meetups rallying the next generation of leaders to tilling the soul in a permaculture workshop.

Group of sheep grazing on grass field

Every detail of this ride is unique, down to the carefully selected homes and hotels you’ll stay in family style with your group of fellow sovereign individuals. We want your ride to reflect an authentic experience of the Midwest - not what some Marketing Manager in New York City thought a Hampton Inn hotel room should look like in Bloomington, Indiana.

A historic building with a covered porch and columns, featuring a sign that reads 'Propylæum'. The building has red brick walls, stairs leading up to the entrance, and is surrounded by well-maintained landscaping, including bushes, flower pots, and trees.

Veteran rider and Bitcoiner Alan Jackson will lead you across the prairies and the hills of the outer Appalachia using the Cornerman System and a detailed itinerary - so you may simply enjoy each turn as you discover the hidden heritage of the American Midwest.

A group of seven people, six men and one woman, sitting around a wooden table in a cozy, wood-paneled restaurant, raising glasses in a toast and smiling.

And as with any Ride of Passage, you’ll do this all with a vetted group of sovereign individuals who are in this for the same reason you are. Remember: you’re not a customer, you’re in our community now. And this community is tight-knit: our group will be capped at 10 riders.

This ride will take you across parts of Illinois, Michigan, Ohio, and Indiana including the foothills of Appalachia along the Kentucky border. We don’t share itineraries before any Ride of Passage to avoid spoiling the serendipity of a good adventure. The itinerary will be accessible to you while on the ride, but we encourage you not to look at it.

Dates and start location below.

Map of the American Midwest and Great Lakes region highlighting key cities such as Chicago, Detroit, Cleveland, and Columbus. The map features icons indicating locations of Bitcoin ATMs or businesses.

Now’s your shot

We only accept 10 riders per tour. Will you be one of them?

American Heartland Tour

Dates: TBD - if you are interested, please sign up below.

Duration: 8.5 days, 8 nights

Location: Starting and ending in Chicago, IL (near O’Hare Airport)

Terrain: On-road, with potential for short dirt road stretches

Ride Leader: Alan Jackson (@pursuingfreedo1)

What you need to do: Get yourself to Chicago and bring or rent a motorcycle - that’s it.

What you get:

  1. Stays in historic farms and homestays ($3,000 value)

  2. Homecooked meals on real, operating farms ($1,000 to do on your own)

  3. Several tours on operating regenerative farms (inaccessible to most)

  4. Professional videos and photos from two days of the ride ($3,000 value)

  5. Unique Bitcoin events and meetups discovered through personal contacts (took Proof of Tour to create)

  6. Packing list to ensure you’re ready to ride (my treat)

  7. Ride of Passage hat, keychain, and more (priceless)

  8. A group of likeminded Bitcoiners riding with you (priceless)

You must bring or rent your own motorcycle - suggestions below in FAQ section. We can help you get a rental.

FAQs: Why take this tour instead of another? What motorcycle will I ride? How about flights? — all of these are below.

  • - A bed in a historic home, hotel, or farmstay every night of the ride.

    - Several homecooked meals on local farms

    - All local experiences

    - Ride of Passage collectible swag

    - Professional videos and photos from two days of the ride

    - Packing list to ensure you’re ready to ride

    You must rent or ride your own motorcycle. Suggestions on where to rent can be found in the FAQs below.

  • Part of the Ride of Passage experience is to release your need to know. While we provide you with a detailed itinerary prior to the trip, we encourage you not to look at it unless you’re lost. That way every day is a mystery waiting to be discovered, with no unconscious expectations limiting your experience.

    What we can say: expect to ride 3-5 hours per day with stops every two hours or so. There is a map on this page which will give you some idea of the places and cities we’ll visit, and I’m happy to give more color when we speak about joining the ride.

Still not sure?

If the info below doesn’t answer your question, shoot me a note at evan@rideofpassage.live

  • With over 40 years of motorcycling experience covering 5 continents, Alan is no stranger to group rides and engine troubles. He’s also one of the friendliest people you’ll ever meet. This guy cannot resist saying hi to the person next to him in line, and if he’s paying for something you can bet he’ll leave his tip in Bitcoin.

    When he joined the first Ride of Passage in Thailand, Alan gave out >$300+ worth of Bitcoin to random strangers he met at every stop. When Bitcoin takes off in Thailand, we will have Alan to thank.

    The American Heartland tour itinerary was planned by me, Evan (Captain Sidd) based on my Bitcoin Tour across the USA, which was sponsored by Swan Bitcoin, Unchained Capital, Bitcoin Magazine, and Upstream Data.

    While I, Evan (Captain Sidd) won’t be able to join you on this ride, Alan and my team joining forces means you benefit from my Bitcoin Tour experience as well as Alan’s much richer motorcycling experience.

  • Simply put, no other motorcycle tour even knows about the stops you will visit or activities you will do, because they aren’t commercialized. They were built on personal connections through the Bitcoin network. You will also have the opportunity to build your own connections in this network as you ride. Big tour operators are entirely disconnected from the world we will show you on this Ride of Passage.

    Additionally, the Ride of Passage is designed as a transformation on two wheels, not just a motorcycle tour - that means we have surprises and events planned for you that no other motorcycle tour operator even considers.

  • If I showed you the itinerary, it would be half as fun. If I tell you exactly where you’re going to go and what you’re going to do, your mind will create expectations (unconsciously!) of what that will be. You will carry those expectations into the experience, and that will limit your ability to absorb everything about that experience. I want you to join this ride as open as possible, not clouded by expectations, so that the journey is as exciting, inspiring and transformational as possible.

    I know that knowing more about what you are seeing and doing can enrich the experience — but that can occur while you’re on the ride.

    Let this journey be revealed as you ride the road ahead. I will share the itinerary with you before the ride just for ease of travel, but you won’t need to look at it. I want each day’s experiences to be a joyful surprise.

  • The two options I suggest for renting motorcycles in Chicago are EagleRider Chicago and Riders Share.

    EagleRider Chicago is located in Des Plaines, IL right near Chicago’s O’Hare Airport. You can find touring motorcycles from $150 - $300 per day depending on model and insurance. I have a contact at EagleRider who can secure group discounts if enough riders rent through them.

    Rider’s Share allows you to rent a motorcycle directly from another individual. This can be cheaper than EagleRider, although you have to consider travel costs and time to reach the pickup point. Look out for the max miles per day as well; you’ll do ~1200 miles in total, sometimes 300+ in a day. These motorcycles come with commercial insurance, and sometimes gear is included / optional as well.

    Keep in mind:

    1. You’ll need to be ready to depart from near O’Hare airport at 11am on October 4th.

    2. You will ride 3-5 hours a day during this trip, so pick something comfortable for you.

    3. You are responsible for ensuring your bike is in working order, as we won’t be able to slow down the trip for you in the case of a breakdown.

  • I’m willing to bet you’d like to never have to ask this question again. That is freedom. 

    I found that freedom for myself now, but I didn’t find my path until I got out of my comfort zone and met people who could show the way. That took a leap a faith, and my 3-month journey across the USA - where I met many of the people I’ll introduce you to - was a massive part of that.

    Take a week off now and let the relationships you build on this trip be the beginning of escape from the rat race. On this ride you’ll meet people from all walks of life who made their own escape.

    If you work at a Bitcoin company: Instead of sending you to a dull conference in an overpriced American city to shake a few hands, take this ride and make many lifelong connections within the human Bitcoin network.

  • For your comfort, I recommend you bring your own motorcycle gear: including helmet, gloves, jacket, pants, and boots.

    Expect brisk fall temperatures and some riding at night. I will include more information on a Packing Guide for you as well.

  • You must get travel insurance in order to ride (which covers repatriation to your country, if you’re not American). You can get this through your health insurance provider. Be sure the policy covers motorcycles and traveling within the USA. The Ride of Passage and its operators and partners do not take any responsibility for injuries or extra costs incurred while on this journey. All participants will need to sign a liability waiver as well.

  • Given the need to book accommodation and experiences in advance, you’ll need to put down a non-refundable deposit in Bitcoin. The remaining balance will be due by a later date specified on your deposit receipt. If the trip does not meet the minimum riders to run, all deposits will be refunded (in US dollar terms).

  • As I shook the hands of hundreds of Bitcoiners across the USA in 2022, I learned that we have more in common than an interest in Bitcoin. We are interested in sovereignty in general: in money, in career, in food, in education, in mindset and more. 

    The Ride of Passage is pointed at sovereignty; we will meet people who went from city life to thriving homestead. People who built unique Bitcoin mining operations revitalizing small towns. People forming sovereign communities and markets built around interest in Bitcoin.

    Every exploration on this journey is pointed straight at the aim of achieving freedom and sovereignty in mind, body and spirit. 

    If that isn’t Bitcoin, I don’t know what is. 

  • Need to store your car (or truck and trailer) for the week? Thanks to O’Hare airport, you have a few options. For cars and trucks the long term parking lot at O’Hare is a great option.

    For trailers, try calling the following lots and asking them if they can fit your specific truck/trailer.

    AF Truck Center

    Park It O’Hare - 847 894 5141

    You may also want to search through HotelTruckParking and ParkSleepFly.

What’s so special about the Midwest?

Led By

Alan Jackson

With a half-century of motorcycling under his belt (across 5 continents!), Alan is practically marinated in motor oil. A globe-trotting pilot by trade, he spends his days giving Bitcoin tips to everyone within earshot and posting it all on Twitter. He was on the very first Ride of Passage in Thailand, and now it's his turn to lead you on a journey through the Heartland of America.

Here’s what we do

  • "Ride of Passage is a fitting name."

    “This experience opened my mind again to the freedom of the open road, and broke through a lot of fears. One of the most action packed and exciting adventures I've ever been on.”

    TechEngineer

  • “I took a leap of faith."

    “The perfect blend of the right place, the right group, the right time, and the right vibe. There is no event like this. I guarantee it will change you to your core.”

    SatSymbol

  • "A phenomenal experience."

    “Evan's team curated meaningful experiences that went far beyond just riding motorcycles and sightseeing. I left with a deeper understanding of myself, the culture I was visiting, and what it means to be self sufficient - not to mention a week of amazing riding with friends.

    Wes

  • “Nothing short of badass."

    “What Evan's team created with this Ride of Passage was no ordinary tour. Far beyond a group ride through Thailand, we participated in pioneering a new international lifestyle based on truth and local connections.”

    Texas Slim

  • "The bar is set high."

    “We trusted Evan's team and traveled halfway around the world, leaving behind family and the comforts of life. What they delivered was an experience few travelers to Thailand would ever have the opportunity to enjoy.”

    Alan Jackson

BROUGHT TO YOU BY

Evan Rally

Evan (AKA Captain Sidd) crossed the USA solo on a Harley in 2022, visiting over 30 Bitcoin meetups and shaking thousands of hands. His team now develops unique trips around the world inspired by his own explorations on two wheels.

A young man with dark hair and a mustache wearing a gray cap and a dark green sports jersey with various logos, smiling while sitting at a dining table at night. In the background, there are blurred lanterns and other people.