Adventure Planning 101

by Justyna Frank
adventure planning

I love occasional spontaneous adventures and outings, but some organized adventure planning will ensure that you optimize the time you have available.

We often complain that summer isn’t long enough, and we don’t do a quarter of the things we wanted to. If we shift our thinking about what constitutes a great trip or an exhilarating outdoor experience, it’s quite possible to pack more of those things into all seasons of the year, without spending a lot of money, waiting for a long vacation, or ideal weather.

Midwestern weather is notoriously unpredictable, and with a scaled view of adventure, and a little advance adventure planning you may be able to more easily take advantage of short pockets of nice weather off-season, and thus significantly extend your outdoor adventure season.

To help you launch an exciting season of microadventures, here’s our surefire 4-step path for going from dreaming to doing, and squeezing the most experiences and adventures into available daylight hours, almost any time of the year.


What inspires you and why?

Many of us love to look at feats of others, only to think: I could never do that. Maybe the adventure is too daring, or too expensive. Or perhaps the adventurer is much younger and fitter. Or more insane.

Or maybe it’s all in our heads. Perhaps it’s not the magnitude of feat that inspires, but the idea of unencumbered freedom, self-determination, autonomy, or something along these lines. What if you could distill that excitement to some essence that could be duplicated in a version of adventure scaled to your abilities, budget and schedule?

For example, I admire bikepackers who traverse distant and desolate lands carrying all their own gear. But the desolation isn’t what I crave. What I actually long for is riding (or wandering) unencumbered, alone with my thoughts, relying only on myself, and free to explore tantalizing detours, preferably free from my cell phone. And that can be easily and conveniently accomplished by doing a solo overnight or weekend trip.

You could argue that there’s no comparison between your local state park and a trek across the Scottish Highlands (and, on a literal level, no, there is not), or you could take my word for it, that a mid-week adventure taken today always trumps the one you have to pine for and may never realize.

What would you love to do?

To come up with your own adventures, think of what you already love to do and gravitate to when you have some free time. Maybe your list includes hiking through piney forests along mountain lakes, or exploring ice-covered beaches, or scrambling along river banks, or climbing hills, or spontaneously taking side roads, or paddling, or camping in the middle of nowhere.

Got a list? Great.

What are you scared to do?

To turn the list of the things you love into a list of potential adventures, think of the things you are too scared to do. For example, when I bike off-road, I am not afraid of climbs, but I am afraid of unknown and potentially technically forbidding trails. I don’t mind pushing my bike uphill because I’ve run out of gears and thigh strength to climb, but I don’t want to sit on the side of the trail and cry because I can’t maintain my footing over rutted singletrack or precarious ridge. Are you scared of rugged terrain, sleeping outside without shelter, going the distance, or traveling alone?

Where is your adventure sweet spot?

The trick is to reconcile what you love and what comes easily with what scares you, and find the the place where a leisure outing becomes an adventure. For example, I could pick a trail that I know to be difficult, and ride only sections of it to build confidence and gain familiarity with the terrain, and plan a detour in case I encounter something really beyond my abilities.

If you’re worried about camping without a tent, would a hammock offer a doable transition? If solo biking scares you, take a class on bike maintenance so you don’t have to fear getting stranded with a flat or other minor malfunction. Or if it’s aloneness itself that’s scary, have a partner or friend meet up with you at a designated spot after you’ve ridden some distance on your own.

Once we’ve met these intermediate challenges, we can set the bar higher.

When we dream up adventures, we put ourselves face to face with unknown. Deciding to actually pursue the unknown is scary, but also very necessary for each of us to become the best self we can be. As we traverse the gap between not knowing and knowing, we learn, adapt and grow. Learning and adapting to the not-known is how we humans thrive.


Of course dreaming alone isn’t going to get you where you want to go. Though I am a big advocate of short, local adventures, if your undertaking involves any amount of challenge, failing to prepare yourself or your equipment could be foolish.

What training do you need and where can you get it?

Your physical fitness needs to roughly correspond to the challenge ahead, but don’t let the desire for perfection keep you from living adventurously. If you haven’t been on a bike in 5 years, it’s probably not a great idea to start with a century ride (100 miles). On the other hand, if you’re generally quite fit but just not a rider, chances are you’d do fine.

However, for most of us, starting with smaller increments is probably a good plan. If you’re starting from zero, and working up to a century, start doing 5 mile rides 2-3 times a week. After a couple weeks, increase by a few miles, and add a 15 mile ride on the weekend. Alternate with some rides when you keep the distance short and go solely for speed. Keep adding mileage every week, and —if you start in early spring— by fall, when most interesting century rides in the area take place, you’ll be ready.

Add a complementary discipline to round out overall fitness. Strength training is almost always a good idea, as is stretching, or a centering and stress reduction discipline, such a yoga, pilates or tai chi.

What equipment do you need?

Depending on the nature of your chosen adventures, you will need equipment. For bike-centered adventures, please refer to our bike guides here and here.

Other than that, you might need cargo carrying gear, camping and cooking equipment if you plan to do overnights, and for any adventure, you will need some survival and safety essentials, and versatile, quality outdoor apparel. Please refer to our Gear Guide and Packing Lists for recommendations of items we’ve used on our outings. It’s never too soon to start assembling your gear, so that when the opportunity arrives, you’ll be ready to go.

What do you need to learn?

I can think of no better resources for self-supported bike adventures than these two:

Adventure Cycling Association. This is the best best and most comprehensive resource for self supported bike touring, which now also features a section on simple bike overnights –an invaluable resource for those interested in microescapes. A must-not-miss for bikepacking and more rugged adventures (and gorgeous photography). Though their headliners are often epic treks through distant lands, they offer solid gear reviews, and inspiring passion for going your own way. They also now have a growing, reader-generated database of local overnight trips.

Prepare or Repair Your Bike

Bike service is our raison d’etre at Cosmic Bikes. You’re always welcome to wheel your bike to our service department, lay out your plans, and let us help you figure out the best course of action. But sometimes, you may need to think it over on your own first, and here are some ideas to help you along:

Assess your bike.

Take an honest look at your bike and decide if it fits your body, and whether it’s suitable for your intended use. This post should help you decide if you can use your existing bike or get a new one. If you’re considering a new bike for your adventures, take a look at our Guide to Adventure Bikes mentioned earlier.

Basic repairs and maintenance.

Our complete Bike Maintenance Guide will help you with everything from doing a basic safety check on your bike to help with your assessment, explaining the need for various types of regular maintenance and repairs, to working with a great mechanic and getting the most out of your service appointment.

Special upgrades.

While your bike is being serviced, or if you’re planning a new bike purchase, consider some out-of-the-box options to really dial in your equipment for your body and your intended use. Yes, options such as building up a custom bike from the frame, or getting hand-built wheels are more expensive, but will also will make an enormous difference in your riding experience and enjoyment.


Trip Ideas

Our shop website contains a compilation of Midwestern destinations easily accessible from Chicago, ranging in duration from daytrips to multi-day expeditions, depending on what your schedule allows. These trips are inexpensive and doable without taking major time off from work. Some are biking destinations, but many offer opportunities for hiking, camping and paddle sports.

This list is a work in progress (and will eventually live on this blog), and we are continuously adding other regional trips and destinations, so check back for more ideas throughout the season.

Add your own

We’ve taken most of the trips listed, but not all in recent memory. We’ll keep updating the travel log with first-hand accounts as we complete more trips this year. You can trace our footsteps, or use our ideas as a point of departure for your own. If you have any Midwestern destinations you’ve enjoyed, please drop us a line! We’d love to include them in our growing guide.

Put it on the calendar!

It’s not real until you commit. Don’t over-schedule, but do pick 2-4 trips —perhaps 2-3 daytrips/overnights and one multi-day adventure, or a ride that pushes your limits— and block them on your calendar. It will really give you something to work toward and look forward to.


This is obviously the best part!! If your bike is in decent shape, there’s no reason you can’t head out right away: this weekend, or even in the morning before work.

Favorite short trips.

For a quick 10-12 mile ride, head out to Moraine Hills or Waterfall Glen. Barring deep snow or ice, these crushed limestone trails are doable on almost any bike, offer beautiful scenery year-round, challenge you with their rolling terrain, and best of all, they are loops, so you don’t have to retrace your steps.

Breakfast Ride.

Our favorite way to squeeze in adventure into less than two hours in to cook breakfast outside, which you can do at the lakefront, or any of the Chicago area forest preserves, such as LaBagh Woods, Skokie Lagoons or anywhere along the North Branch Trail.

Join others.

If you’re reluctant to venture out on your own, join others, and benefit from experience of people who’ve already done this, before you decide if you’re ready to venture out on your own. In Chicago, Out Our Front Door organizes a number of overnight camping trips led by experienced volunteers, departing from Downtown Chicago throughout the year.

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