The Mafia Holiday Ride in Chicago


The Mafia Holiday Ride (or simply “Mafia Ride”) is a group ride that leaves from the Deerfield Train Station at 7:30AM on holidays or holiday weekends only. The ride usually occurs on Easter, Mother’s Day, Memorial Day, Father’s Day, and Labor Day. It’s a good idea to check the Mafia Facebook Page to confirm the dates, as rides are added and removed based on weather. The course is a 54-mile loop heading up north and back. You can see it below.

What to expect on the Mafia Ride

The Mafia Ride is a large and FAST group ride. The ride does not stop for mechanicals, flats or dropped riders. Therefore if you get dropped, prepare to either take the shortcut and regroup, or ride home alone. The ride can have anywhere from 20 to over 70 riders. And the riders’ abilities vary widely, so plan to see some carnage at the back along with unsteady wheels and basic stupidity.

I do the ride to see friends and improve my group riding (crash avoidance) skills. My general goal for the ride is have fun, stay save, and avoid crashing. In this last ride over Easter, I had the added goal of riding with Theia and keeping her connected and safe too. We mostly accomplished that goal until the group decided to run a full red light with incoming 4-lane traffic. I made it through, but Theia stopped.

The ride is fairly easy if you ride in the middle of the pack so long as you know where on the route the pace changes and prepare for it. Here are the pressure points:

  • First 14 miles are “chill” with some accelerations, but nothing insane.
  • Around mile 14 the speed picks up heading due North. You can expect the pace to be over 30 mph at times between miles 14 and 25.
  • The east/west section between miles 25 and 28 can be hard in the crosswinds. The road and shoulder were repaved recently, so except for the rumble strip and traffic, this 3-mile stretch is great.
  • Once you turn south at mile 28, the next 10 miles can get very fast. The pace surges a lot and separations happen on the flats. Make sure to close down any gaps immediately or you will get dropped.
  • After mile 38 it’s pretty chill until the last section of road coming down Waukegan. The ride ends in a sprint to the Deerfield Train station. Stay out of that mess unless it’s your “thing”.

How to avoid getting dropped on the Mafia Ride

Here is how I recommend you avoid getting dropped.

  • Never ride on the front unless you know you belong there.
  • The unwritten goal of the ride is for the strong riders to drop everyone. Know that going in and plan accordingly.
  • The first separation happens around mile 17. There is a small hill then left turn at a light. If you are off the back going up the hill and miss the light, it’s game over. Move up BEFORE the hill. Get mid-pack by mile 15 or 16. Every ride people blow out the back on this short hill, so unless you are strong enough to bridge multiple gaps, move up before the hill. You can see it happen HERE.
  • After mile 14 expect every turn to be full gas. Be ready to sprint for 15 seconds out of every turn, especially in the back. Ride closer to the front if you don’t want to sprint as hard.
  • There is another small hill around mile 22 where people get dropped. Move up before the hill and prepare to go hard up it.
  • The group has no problem running red lights full speed. I don’t know why and think it’s incredibly stupid (I have a wife and kids and want to make it back home). But know this going in, and again try to ride mid-pack. Running a red from the back of the group is even more dangerous (like I did unfortunately). If you want to see this immense stupidity check it out HERE from the last ride. In all honestly, I should have stopped. There was no reason to run this and once I bridged back to the group I ended up stopping to wait for Theia anyway.

The shortcut to reconnect if you get dropped

If you do get dropped from the ride there is a shortcut you can take heading west. Normally the group turns west at 104th Street. Riders that get dropped around mile 22 can do the following:

  • Turn West on 122nd Street
  • Cross over the 94/41 and turn South on 120th Ave
  • Immediately turn West on 128th Street.
  • This will hit Hunt Club Road (136th Ave). Turn south here and the group will catch you shortly.

The shortcut saves about 10 minutes, so don’t dilly dally around. Head south on Hunt Club and ride tempo. After running the red and then stopping for Theia, we took this shortcut and picked up a few riders along the way. The group eventually caught us. The faster guys really don’t like this shortcut. The fast group is safer with fewer riders. But I had a legit reason to take the shortcut so I don’t feel bad this time.

This is the FULL Mafia Ride route (without the shortcut).

In Summary

The ride leaves at 7:30AM sharp and can get very large if the weather is nice. If you don’t like riding with 50+ of your “closest friends” don’t do this ride. Every time I do the Mafia Ride something dumb happens including: running reds, touching wheels, bumping, etc. There can be jockeying for position, but it’s not a road race. People will let you in: especially if you are strong. Watch out for carnage at the back. Nothing good happens in the back, but if this is your first time doing the Mafia and are unsure if you can hang it’s probably safer for everyone else for you to ride in the back. You will likely get dropped, but in the back you won’t take out the group.

The ride is fast and surges. It simulates a road race so prepare to go hard out of all turns. The crosswinds can be brutal and they change from ride to ride. The ride is easiest in the top 1/3 of the group. Because the ride can get very fast, close down every gap immediately. DO NOT WAIT. Every hill is hard, but none of them are longer than a minute or two. I think the unwritten goal of the ride is to drop everyone. So if you don’t get dropped, you won the ride (in my book).

I hate to sound like a “bike snob” but don’t wear a Pearl Izumi jersey that flaps in the wind. This is a fast ride with some real animals. If you are going to do the ride, get aero and look like you belong. Old kit that doesn’t fit is for the trainer, not the Mafia Ride.


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