Sorry if this is an already addressed topic which I just missed, but I am curious what the worst/scariest road on your daily commute. I am talking about traffic, careless drivers, hills anything.

Myself here in Minneapolis it is the stretch of Lake street inbetween Minnehaha and 4th street (where the trail starts). Although this is only about 2 miles of my commute, it really can be quite dangerous at 8:30 rush hour. Huge traffic, giant potholes and ruts forcing you half way into the middle of the street, giant buses cuting you off etc. There are other routes, but something about riding along with the traffic makes me go faster. I will probably change it when they finish the Greenway Corridor closer to my neck of the woods.

I climb a hill on my return trip home that is a 12% grade over .7 miles. The thing is murder! Funny thing - I don't even have to go this way unless I choose to. . . and I do about once a week. I'm striving for CKOM (Commuting King Of the Mountains) in this town

Edit: And I'll also add that I only have a double (39/25) and I also have loaded panniers, so it is a bit of masochism.

Washington Street from Sullivan Square into Union Square is so full of potholes and traffic and busses and lotsa UPS trucks in the morning (the depot is right there)... but its the potholes that really make it annoying. All the roads around here seem to be falling apart. At least we have the Big Dig though.

Overall, I have pretty good semi-rural roads most of my way to work. 26 Miles. I would say 2-3 miles do I feel to be riskier. Most of the roads I travel have wide bike lanes and light traffic.
The two miles. No shoulder to speak of and high traffic.
St Route 79 south, entering Temecula has very high traffic volume as you approach I-15. There is enough room to share with cyclists in the right lane if the motorists chooses to. Luckily, road officials have put in a pedesterian cross walk under the freeway on ramp. With the pederterian 'cross walk' light flashing that is the ONLY way, traffic entering the on ramp WILL stop.
The other one mile is on Winchester Road, St.Route 79 north.... No shoulder and lots of traffic. For just one mile.
22 miles of relative comfortable riding. That is good.
Worst bike maneuveur is negotating traffic and lane crossing at freeway entrances.That is scarry.

Well the ride home has a hard climb 1/2 mile from my place. Really a killer, especially when the wind is normally in my face the whole ride home. I won't complain about traffic out here. I got it way better than a lot of you folks in the large cities.

The good trade though is that I can walk down to the pub and do the crossword puzzle over a Belhaven by candlelight... so sometimes I can accept the traffic as a necessary evil... and... it is fun to dance with the cars sometimes.

Yeah I pick out a particular car when I start riding on a busy street, and he is my mark. I then try and beat them to a particular point, usually where I have to turn off. I would say 70% of the time I win, especially when the traffic is bad, I can just slither my way through the traffic jam.

The roads are fairly smooth around here, or at least smooth enough for my MTB with 1.75" tires and suspension fork. But there is a stretch through a semi-industrial area where I have on occasion been stopped by trains at adjacent tracks. Trains that are in no hurry to get anywhere.

With the three new offices that I just aquired, one is on Chicago and Lake, and I have to work there one day a week so I'll be dealing with the stretch from 4th to Chicago so I hear yah (I've done it before for meetings). Of course mine is a tiny stretch compaired to yours, I don't envy you. Other wise, my regular route is about 95% quiet easy riding, I've just got this 3/4 mile stretch by my house that can be a little dicey with the narrow road and traffic.

The majority of my ride is quiet residential streets, but the last one is horrible. It is a six lane rode with a bike lane. The speed limit is 50/km but the average speed is around 80/km. The police have radar set up 2-3 times a week. Never works. I jump onto the side walk for this one. Even riding the bike lane here scares the willies out of me. Its full of crap and the cars pay no attention to anything. Gives me nightmares just thinking about riding on that road.

Coming back home on Hermitage, there's a section where I go under a bridge which carries the I-95/I-64 traffic. On the far side of the bridge, there's an exit ramp from the freeway. Although there's a stop sign at the end of the ramp and visibility for the cars is limited by the bridge supports, very few of the cars come to a full stop. This is a section I exercise great care on, needless to say. Too bad Hermitage is basically a straight shot to and from "work" and little travelled compared to the other possible routes.

The Esplanade in Surfers Paradise. Potholes everywhere, and the highest moron quotient in Australia. But for the notoriously slow Queensland traffic lights, I'd ride the six-lane Gold Coast highway instead.

I've got a one mile stretch of 4 narrow lanes with curbs and slightly uphill. 35mph limit, but no one does less than 45. Getting 2 foot of clearance from a passing vehicle is a miracle on this stretch.

The roads on my commute are good with bike lanes for the most part. The only dicey point is where Martin Way goes under the I-5 freeway. Both directions the commute involves freeway traffic exiting & entering the freeway through the bike lane. There is a Top Foods Super Market entrance that has a similar situation where traffic from the 4 lane arterial exits through the bike lane into an entrance lane to the market. Kind of freaks you out to have vehicles traveling at 40+MPH passing on your right and left but you get used to it and it doesn't happen often. Also, My commute has very little traffic in the morning and only light traffic in the afternoon. Some of my co-workers arrive & leave later during the full rush hour & it sounds like they have a worse commute than I do. Don

On my commute there is about a stretch of Springrove Ave that gets bad in the afternoon. There is about a mile of it that gets narrow and traffic gets pretty backed up up there. The lanes get narrow and there are a few lights right in a row and they do not let to much traffic get through at a time. On intersection on that stretch leads to the on/off ramps to I-75 and gets heavy traffic in the afternoon. I need to be on my toes on that mile because cars are always changing lanes jockeying for position.

I don't have any freeway entrance merges on my commute. I hear they are trouble-spots.

In general, there are a few things that make it dangerous for me when I encounter them:

1) Dangerously rough pavement. I try to avoid this when possible.

2) Debris from wind storms, ice, etc. This can be strewn far out into the lane so I have to anticipate my moves well in advance.

3) Fast downhills. One of the things that makes biking safer in my opinion is the slower speeds I travel. 30 mph to 40 mph is fun, but a potentially serious crash, too. No margin for error, here.

4) Blind hills/corners. My horn and lights come in handy here. When an motorist approaches me on one of these from ahead or behind, I might beep to let them know I'm there. This also applies to busy intersections, sun setting behind me (blinding motorists to my presence,) etc.

I'm not as concerned about being hit by motorists while I'm upright as I am about crashing due to road conditions or my mistakes while I'm surrounded by traffic. That's how that lady in Boston was killed. She she was doored in a bike lane and she bounced into traffic, under the wheels of a bus. So debris, road imperfections and similar hazards (like dooring) concern me more than traffic itself.

this is the worst for me.

When I lived in California, I was blown away by all the people who chose to ride on the narrow and winding Hwy 1 which has perilous drops next to the ocean. These weren't commuters; they were taking their vacations!

I did something similar out here last year, the Great Ocean Road in Victoria. One of the most inspiring cycling experiences I've ever had -- I'm planning a return one day.