I should point out audio books often cost money, but many, many podcasts are free.
I like:
The Fredcast cycling podcast
The Spokesmen cycling podcast
Fresh Air (npr)
This American Life
The Moth
Planet Money
Freakonomics

all are free!

Yeah, I'm getting more than my money's worth from my yearly donation to NPR!

Car Talk
Lake Woebegone
Planet Money
This American Life
Radiolab
Wait Wait Don't Tell Me
Will Shortz' Sunday Puzzle

I ride solo almost exclusively since most of my riding is my commute (about 40 minutes each way). I typically tune into NPR or a pandora station and just keep the volume to a level where I can hear my surroundings still.

Is that using a smart phone? Does your plan let you stream that much without costing zillions?

I just ride with music on solo rides. Even then it's tough but you just have to keep going.

On the road, the scenery keeps me distracted.
In Prospect Park, where there are plenty of female joggers, the scenery keeps me distracted.

+1

OP is in southern california, right? There's got to be a ride to a beach with nice "scenery" he can take in.

That would be awesome! But sadly I live inland and closest beach is 70miles round trip(I ride to there every other weekend )

I'm certainly a proponent of learning, but wouldn't having your mind engaged in paying attention to content mean it's much less engaged in the task at hand and the whole not getting run over thing?

+1

It is using my iPhone. I've got unlimited data (grandfathered in) and is relatively affordable bundled with a family plan and corporate discount.

my podcast rotation subscriptions

two johns cycling podcast
wtf with marc maron
comedy death ray radio
this american life
radiolab
freakonomics
the nerdist
doug loves movies
planet money
savage love podcast (not for everybody)
slate political gabfest
slate culture gabfest
npr story of the day
the moth

several others that i listen to irregularly but those are all pretty solid and update pretty regularly.

in a decade of 10K miles a year i've yet to be run over, and of the accidents i have had, i cant say listening to music or podcasts was a factor in any of them. if you can drive a car and have a conversation with a passenger, i cant see why operating a bicycle and listening to a podcast would be unmanagably taxing of your attention.

but its your call obviously.

I think most cyclists are introverts. You're probably an extrovert. I'm totally fine when out there on the road for 4 hours or whatever, even without music. In fact, oftentimes when I have music playing, I have to turn it off after "a while" because it's distracting me from my meditation.

Plus spring is in full swing now, so there's plenty of greenery to look at. I have no advice for you other than to keep your rides short enough to bear so you don't get burned out. Besides, 20-30 miles is plenty of time to get a good hard workout in. In fact, it's the perfect amount of time.

Bike + iPod + Open Road = good times...

Didn't realize Dan Savage had a podcast. [goes to iTunes to subscribe] Thanks.

I have solo training rides on Tues/Thurs during the week. Sat is when I have my 60mi+ fast paced group rides. The hard part of my training rides is getting motivated to get out the door after a long day of work. I usually have the same 30-40mi. route w/ ~3000ft. of climbing. When I ride solo I usually treat it as a TT and try to improve every time. I'm so focused that the thought of riding solo doesn't cross my mind.

Glad I'm not the only one who finds cycling meditative. I never listen to anything other than the wind (and unfortunately traffic) and have never ridden with anyone (the introvert part I suppose).

Thanks for the tips everybody! I am planning a new route for tomorrow's ride.

I always try to time myself but there is a huge variation in times because of traffic and signals.

I used to do a lot more rides where I saw a paved road going off to the right and decided to take it to see where it leads ... and ended up cycling the countryside, sometimes getting lost temporarily, and sometimes doing something like accidently riding a century or other long distance finding my way back. Where I live now, it's a bit more challenging to do that because this area is very hilly and you could end up on some monster climb.

However, we will look at a map and decide to head off in this direction on a Saturday to see what there is to see over there, and another direction on the Sunday to explore a different area. If there's something out there to see, even better!

check to see if any were involved in an unsolved murder.

i really do think you are on drugs

This is funny! But, next time, try wearing a Superman cape and mask. Try riding fast enough to lift the cape in the air--typically around 22-26 is where I get lift off. After the initial push you will have to work harder to keep the cape from entering the spokes and rear sprocket. But if you don't have the cape and mask, the imaginary friends would work, I guess

---begin rant---
I'm a little worried by the fact that people get bored riding their bikes solo. If cycling is a hobby, you need a new hobby. If it's a social thing, always ride with friends or make up your own friends or make calls with a bluetooth headset. If you cycle to get in shape, HTFU. I sit in classes everyday and wonder about the state of my peers when they can't keep their cell phone in their pocket for 50 min.
---end rant---

Nature, my own thoughts, and podcasts have always done it for me, in that order.

Add 'Stuff You Should Know' to the growing list of recommended podcasts.