Here is a list of bike races in the Chicago area, plus things to do on a bike for May of 2025. Events are divided into races for competitive cycling, and rides for social outings or non-competitive endurance events (like brevets).
Pic from The Garden, Chicago’s north side bike jumping park.
Published April 25, 2025
Tailwind’s Pit Tips for Criterium Racing
What is the Half Acre Cycling Skyway Crit?
Who and What: The Half Acre Cycling Team puts on an annual two-day road bike racing event called the Skyway Criterium. It’s a lap race open to anybody at any skill level. Prizes come in the form of medals and pride.
When: Saturday & Sunday, April 19 & 20, 2025
Where: The road and area around the Calumet Park gymnastics building, on Chicago’s southern edge. The course goes in a bean-shape on S. Ave G, Crilly, and 100th Dr.
Tailwind Neutral Support at the Race
We are extremely happy to be given the opportunity to help out with the Half Acre Cycling Skyway beginner Criterium series this upcoming April 19th and 20th. The importance of Half Acre Cycling’s commitment to inclusivity and effort to bring new bike racers into the Chicago racing scene is huge!
@boxwrenchben has been a race mechanic for twelve years now, having gone to the US Olympic Training Center in Colorado Springs to obtain a professional mechanic’s license in the fall of 2012, and worked Neutral Support professionally for the first time for NRS and Events in the Spring of 2013. He has worked as a neutral support race mechanic or pro team mechanic at races every year since 2013.
The Skyway Crit Series is great for new racers because the course is beginner friendly and the focus is on the lower categories, rather than some of the bigger race series in the area that cater to Category 1 and 2. A big part of crit racing that is often overlooked by new racers is how the race pit, technical assistance, and free laps during the race all work. The foundation of providing neutral support at a race is being able to provide technical assistance to the racers while at the same time adhering to the rules of the race, and also helping racers re-enter the race safely after taking a free lap. One of the requirements of obtaining a USA Cycling mechanics license is to take and pass the USA Cycling Officials license test. This ensures that the mechanic can work with the race officials to make sure everyone can race safely and fairly.
A lot of bike racers (new and experienced) don’t actually have a great understanding of how neutral support, the race pit, and free laps work at a race. We’ll go over some of the fundamentals here, and don’t be afraid to ask the mechanic(s) in the pit (whenever they aren’t busy) or any race official (same) if you have any questions. You can also go to the USA Cycling website and download a pdf of the official 2025 rulebook. Criterium racing rules are covered in chapter 3:
Any and all technical support must take place in the pit, no matter what point it is in the race. No rider is allowed to take a new wheel or have their bike worked on anywhere on the course other than the pit.
Don’t, under any circumstances, run into the pit and just grab a wheel for yourself or any other rider! (thankfully nobody has done this at Skyway any of the years I have worked it) You have to be given a spare wheel by the mechanic in the pit. If there was a big crash and there are multiple riders in the pit, this is especially important. It can be hard to be calm when your heart rate is up and your adrenaline is pumping. I can assure you though, if you just grab a wheel without permission and re-insert yourself into a race, you’ll be disqualified and that’s the end of your race.
You are expected to have your equipment in reasonable racing shape before the race. Neutral support is not a replacement for regular maintenance. If you come to the pit with a non-race incident mechanical, you will not be given a free lap. You can still re-enter the race, but you will either be chasing the field or you will be a lap down. Incidents where I have seen a racer not allowed a free lap include, but are not limited to: Bike stops shifting because derailleur cables are corroded. Bike stops shifting because it has electronic shifting and the rider forgot to charge their battery. Chain is skipping badly because it is so worn out it won’t engage cogs properly. Bike got a flat tire, but tires are worn way past the point they should have been replaced. Tubular tire comes off due to glue being old, or tubeless tire goes flat due to sealant being old and dried up. Bars, stem, or seatpost slip due to having damaged bolts or not having been tightened properly. Don’t be that person. Bike shops like Tailwind are here to inspect your bike before the race. If you have a race incident during the race and it is still in the part of the race where free laps are available, you are instructed to make your way to the pit as quickly and safely as possible.
A race incident is defined as a mechanical failure not caused by lack of maintenance, or a crash the rider was involved in. Being involved in a crash is defined as actually ending up on the ground. Stopping or slowing down to avoid a crash unfortunately doesn’t make the rider eligible for a free lap.
In most criterium races (including Skyway) you are allowed to cut the course or travel against the race direction (not on the course) to get to the pit.
At the line before the start whistle, the race officials will announce which race lap free-laps will end. Please pay attention to that announcement. You will also be told when you arrive at the pit whether you are getting a free lap or not.
If you come into the pit alone, you will be pushed back into the race by the mechanic. The intention is to get you back into the race pack in the same position as you left the group for the incident. Please wait for instruction on when to start pedaling and take the push. Either all of the riders re-entering the race get a push, or no riders get a push. At Skyway, there is only a single mechanic in the pit, so if there is more than a single rider re-entering the race, those riders will need to stand and wait to be told by either the mechanic or officials when to start pedaling to re-enter the race.
Come on down and check out the races! The cost of entry is low and day-licenses are available at registration, but we recommend you pre-register to make sure you get a spot.
Here’s a shot of Ben pushing a rider back into the field during the Tour of America’s Dairyland.
Published April 1, 2025
Fueling Your Ride with Tailwind: Nutrition and Hydration for Cyclists
The ancient wisdom says that you should be hungry by the end of a long ride, but the latest science shows that you should actually be comfortably fed the whole time. Modern cycling nutrition strives to get as much fuel into your body as possible without hitting the hard physical limit – known as your puke factor. The professionals in the world tour races eat 120 grams an hour or more, which adds up to 5,400 calories a day, almost three times the amount a normal American consumes.
Why Is It So Important to Eat While Riding?
The amount of steady energy output your muscles can exert is partly a function of how much fuel they have, in the form of glycogen. So long as the glycogen’s there and metabolic waste is managed, your muscles can keep working almost indefinitely. The easiest source of muscle glycogen comes from simple carbohydrates like brown sugar, but fat, protein, and salt also help keep you going, and a little ginger keeps the mixture from coming up. The nutrition products Tailwind recommends balance these factors to get you the fuel you need while also helping you keep that fuel in your stomach.
Our Products and Why We Like Them
Tailwind
Source: Tailwind Nutrition
No relation to the shop! But we do like the name. Tailwind started on a hot day at a bike race with the founder’s head in a trash can, spewing out the “nutrition mix” recommended by other riders. He thought there has to better way, and after research and experimentation he came up with the formulas now used in Tailwind nutrition products. These gels and hydration packs are made to be palatable and easy on the gut, especially on long, brutal rides or races. We get great feedback on these products.
Gu
Source: Gu Nutrition
The grandmother of sports nutrition, Gu has been selling energy gels since 1993. They have an impressive selection of science-backed products including chews, gels, drink mix, cookies, and capsules in a variety of flavors. Gu products work for any type of endurance athlete and they’re one of the most popular choices.
Scratch Labs
Source: Scratch Labs
Scratch is best known for their hydration options, which come in several flavors, with vegan options as well. Their hydration mixes were developed specifically for professional cyclists, and are able to hydrate better than plain water due to their electrolyte blend. What makes them different than something like Gatorade is less sugar, more sodium, and no artificial flavors or colors – just real fruit. Scratch is one of the most popular nutrition brands we sell.
Untapped
Source: Untapped
Using pure Vermont maple syrup as its primary ingredient, Untapped offers highly digestible nutrition with few highly processed ingredients. Maple syrup makes a great endurance fuel because it is low glycemic, meaning it digests slower than regular sugar, so you refuel your muscles without sudden energy dips. It also has natural amino acids and antioxidants, plus it’s water-soluble so it goes down easy and stays in your stomach.
How Much Should I Eat and Drink?
That’s a question with varying answers, but generally if you are out for part of the day you should aim for 60-90 grams an hour, which equals one or two gel packets. For hydration, most experts suggest you drink before you get thirsty – so take a swig every fifteen minutes or so, depending on how hot you get. The longer and harder your ride, the more you should imbibe, up to the point where you feel sick or heavy-in-the-gut, of course. With practice, you may be able to eat as much as 150 grams an hour, which will keep your energy levels topped up.
For short rides lasting less than an hour you probably won’t drain your glycogen stores or need major refueling. You should still eat something like a single gel pack after your warm-up because studies show activating your taste receptors and getting your gut juices moving lets your body release a little more energy than it normally would.
Personal Story: Gas Station Nutrition versus Tailwind-Approved Nutrition
The Fall Color Festival in southern Wisconsin is 22+ miles of rough single track where a hundred riders are let loose all at once. The first time I raced it I only had 1 water bottle, and my nutrition consisted of candy bars and granola packets I picked up at the gas station on the way up. I figured that would be plenty for just 22 miles, as I had ridden that far before on just one bottle and some snacks.
The race ended up taking three hours. I was the third-slowest finisher and felt like I was going to die when I finally made it to the finish line. It took me days to recover, and in hindsight I think I had a minor heatstroke.
The next year I raced it with a full compliment of Gu gels and chews, plus Scratch Labs hydration in my bottle with plain water in my hydration pack to wash it down. I set my Garmin’s timer to remind me to eat and drink every 15 minutes too, just in case.
Despite having the same fitness levels between both races, my second attempt finished 30 minutes sooner than my first. More importantly, I felt great the whole time and even sprinted against another racer at the end – just for fun of course, we both still finished 45 minutes behind the race leaders.
After the race I drank Scratch Recovery Mix and felt good enough to ride my bike to work the next day. Yeah, I was tired, but not dead like the year before.
Final Thoughts
If you’re new to cycling nutrition, it’s a good idea to grab a bunch of different brands, flavors, and textures to see what you like best. Use them during low-pressure training rides and never try something new on a race day. Once you figure out your preferred brands and delivery systems, work on stomaching as much as you feel comfortable with to keep your glycogen stores topped up. Have questions? Ask our friendly staff or one of the team members out at Chicagoland races.
Published March 10, 2025
Fighting Bike Theft in Chicago: Statistics, Trends, and Prevention Tips
Bike Theft Statistics
Bike theft is up 15% in 2024-25.
Most bike theft occurs in sheds and garages, not out in the open.
The thefts that occur in the open involve cutting or disabling a lock, meaning the theft was planned and executed with specific tools.
Most theft happens at night in late spring and summer.
The most attractive bikes to steal are hybrids and other city/commuter bikes worth less than $1000.
Learn more details from Bike Index, and while you’re there, make sure to register your bike.
Why is Bike Theft Growing in Chicago?
The short answer is that cycling is becoming more popular. Chicago is the fastest-growing city for cycling in the nation, after all, and there are more bikes on city streets than any time since the turn of the century. This popularity means there’s a market for stolen bikes, and a growing number of potential victims. This post explores the products and methods Tailwind recommends to keep your bike safe from thieves.
How to Thwart Bike Thieves
Locking your bike to something solid is the best way to keep it from getting stolen – even when it’s already on your personal property. At Tailwind, we carry high-quality locks from Abus, but it’s important to understand their product line and when to use each type of lock. Here’s a quick rundown of the types of locks we sell and when to use them:
U-locks
These are the most common type of lock in Chicago, and for good reason. The design is simple and it fits in a backpack. Bang for buck, u-locks provide the most security at a given price point. The Abus Granit series will cover the needs of most cyclists as it can only be defeated by an angle grinder, which takes time and creates a lot of sound, sparks, and smoke. For even greater protection, the AbusGranit Super Extreme 2500 can even fend off power tools. Use this lock when you need to leave your bike in the loop overnight but be careful what you lock to. A thief might think it’s easier to cut down the bike rack instead of the lock.
What makes Abus special and why do we prefer them? For one, they have offices in Chicago and understand the unique needs of all-year cyclists in the Great Lakes region, so their locks hold up against snow, rain, and salt. But from a security standpoint, the way Abus u-locks are constructed means they have to be cut twice to fail. Most other u-locks on the market fail after just one cut. Also, all Abus locks are made from hardened steel, whereas cheaper locks off Amazon.com are made from softer steel that cuts more easily.
Source: Abus
Folding Locks
These locks seek to fix some of the problems with u-locks, mainly that they’re bulky and hard to get around some objects. Folding locks retain a lot of the security of a u-lock but fit in a coat pocket. The Abus Bordo series come in lightweight and heavy-duty versions, and the 6500 series will work for commuters who leave their bikes at the train station during daylight hours. A big perk of Abus folding locks is that they come with elegant holsters that attach to water bottle cage mounts on almost any bike frame.
Source: Abus
Chain Locks
These locks allow you to secure oddly shaped objects to each other. They’re also easy to store in a backpack or pannier. The Granit Citychain Xplus grants the most security in this line. Like Abus u-locks, all Abus chain locks require two cuts to fail.
Pro tip: you can combine an Abus chain with an Abus u-lock to secure more bike components or to give you the versatility to lock to awkward objects.
Source: Abus
Goose Locks and Infinity Loops
Sometimes you don’t need maximum security and a lighter, easy-to-use lock can do the job. For these tasks we suggest the Goose Lock or the Infinity Loop. The Goose Lock is flexible, but it holds its shape. This is a nice feature in winter when you’re wearing bulky gloves and it’s also nice in low-light conditions because when you let go of an end you don’t have to worry about it falling to the ground limply.
The Infinity Loop works like an adjustable length of rope, allowing you to get a snug fit when locking. This is great for CTA bus users and Metra commuters because you can lock firmly to the racks so the bike won’t jostle about.
Source: Abus
Cable locks
Sure, a cable lock is better than nothing, but not by much. At the shop, sometimes we can cut through these locks with one hand and a pair of snips. These locks should really only be used to secure parts of the bike, like saddles. For long sporting rides it’s a good idea to carry a light cable lock in case you have to lock up for a minute to use the bathroom somewhere.
How to Properly Lock a Bike
Four words: Frame, rear wheel, rack. Ideally, you want to lock these with one lock, then use a secondary lock to secure the front wheel to the frame. After that, a cable lock through the saddle will send a strong message that your bike isn’t the one.
At the very least, lock your frame to something sturdy. According to Bike Index data, thieves want the entire bike, not just parts off of it – but they’ll take what they can.
More advice: don’t lock to trees or wood fences, they can be cut (and your lock hurts the tree bark), and avoid locking to street signs, as they’re designed to be easily removed by city workers. Parking meters are typically good for u-locks so long as you can’t just lift the bike up and over the head of the meter.
Note that any bike lock can be defeated by somebody with enough time, tools, and effort. Even if you have an unbreakable lock, a thief with a van can pull the bike rack out of the ground.
Need a bike rack? We can help you out with that too, but give us a few days to special-order it.
Final Thoughts
The crew at Tailwind have been riding and locking bikes on city streets for decades. We know a few tricks and tips beyond what’s mentioned in this article. Feel free to come by any time to pick our brains.
Published February 24, 2025
The Tailwind Gift Guide for Chicago Cyclists
Chicago cyclists don’t all hibernate in the winter, but the city’s cold winds and icy roads demand gear that ensures both warmth and safety. If you’re looking for the perfect gift for a winter cyclist, here are some recommendations that will make their rides more comfortable and enjoyable.
Bar Mitts
Bar Mitts are a must-have for any winter cyclist. These handlebar covers provide excellent protection against the cold, keeping hands warm even in the harshest conditions. Made from neoprene, Bar Mitts are windproof and water-resistant, ensuring that cyclists can maintain a firm grip on their handlebars without sacrificing warmth. They are easy to install and remove, making them a convenient addition to any bike. The big advantage of using Bar Mitts is that you do not need big, clunky gloves, so it’s easier to manipulate the shifters and brakes. Available for any style of handlebar, including road and mountain bike.
45NRTH Balaclava
The 45NRTH Balaclava is designed to offer protection against the cold while maintaining breathability – but also durability for year-after-year use. Made from a blend of merino wool and synthetic fibers, this balaclava provides has anti-microbial properties built in, and is also machine-washable. It covers the entire head, neck, and face, leaving only the eyes exposed. Pair it with ski goggles for full-face coverage. The ergonomic design ensures a snug fit, preventing any cold air from seeping in. One size fits most!
45NRTH Sturmfist 5 Gloves
The 45NRTH Sturmfist 5 Gloves are specifically designed for winter cycling, featuring a combination of merino wool and synthetic insulation and an ergonomic fit that contours around the handlebar to avoid the finger-bunching you get in non-cycling gloves. The outer shell is windproof and water-resistant, while the inner lining provides excellent warmth and comfort. Pro-tip: if you’re between sizes, remember that your hands tend to swell while riding, so consider sizing up.
Continental Top Contact Winter II Tires
Safety is paramount when cycling in winter, and the Continental Top Contact Winter II Tires are designed to provide superior traction on icy and snowy roads. These tires feature a special rubber compound that remains flexible in low temperatures. The tread pattern is designed to channel water and slush away from the contact patch, reducing the risk of slipping. Studded tires are a good option, but on Chicago’s mixed terrain, with ice, snow, and bare concrete, the Top Contacts offer better flexibility. We have these tires in multiple sizes, so it’s a good idea to bring your bike into the shop to get it properly fitted.
What Else? Consider Gifting a Fit or Tune-Up!
Tailwind Cycles offers fit services and bicycle maintenance year-round! If you’re looking to buy the cyclist in you life something that they’re guaranteed to use, look into a service package with Tailwind.Follow the blog for more info and check out our Instagram @tailwindcycles to see what we’re working on right now!
