When to bug out? Excellent question.
Ideally, the best time to bug out is an hour before an emergency crisis hits (or before the rest of the population learns of it), the roads would be normal, gas still available, stores no more busy than usual...however, short of ESP or a crystal ball, I don't know to see the future before it gets here (...if you manage to find a way to do so, I'd appreciate a tip on it

).
Realistically, the best way to know when to bug out is by situational and environmental awareness. Watch the news every day, listen to what your neighbors and coworkers are concerned about...is there a hurricane off the coast headed your way, are there any concerns in the news for a terrorist action in the near future, are the local merchants worried about a union strike cutting off the flow of food and goods to their stories (resulting in shortages and possible rioting/looting), have there been any "social" incidents that might spark civil unrest and violence in the streets (such as a police shooting of an immigrant, minority or unarmed suspect, local politicians cutting off government services due to tax shortfall, etc.).
The things to look for really vary depending on you, your situation and your location in the country, as the potential pitfalls are different in each person's case, so take stock of your situation to see what effects you the most.
There are certain red flags you should think out and discuss with your family, to decide in advance when you will say screw it and hit the road.
If there are angry protests over government cutbacks of services and protesters are rioting, breaking windows and setting cars on fire at city hall...and you live out in the burbs, you are probably safe to hunker down and stay put.
If there is a trucking strike that shuts off the flow of goods to area markets and food is flying off the shelves and not be restocked, you are probably okay to live on your reserve foods, but to be on the safe side you might want to keep the doors locked, a gun loaded and keep your ear to the ground in case things start to deteriorate. (Again, it depends on where you life).
If there is an train wreck and a huge cloud of chlorine gas is forming from leaking tanker cars...and drifting towards your area...grab you BOB, lock up the house, move any important stuff you absolutely need to the car (meds, shotgun, the kids, the pets, etc.) and get rolling.
If there is an outbreak of a new strain of mutant virus, for which there is no cure, and people are dying in the streets of downtown, and the governor has ordered a state of emergency, and the national guard is moving in to quarantine your area...don't even turn off the T.V....grab your BOB, wife, kids and fly like the wind...otherwise you'll find yourself in a traffic jam where nobody is moving and the national guard is instructing everyone to go home from behind the business ends of M-16s.
You really need to think it through and work out what and when you'd bug out in advance...and then keep your ear to the ground in case any of those events come to pass. If events unfold and you no longer feel safe, that should be a red flag in and of itself. If the event is as bad at you thought it might be, you will have been very wise to run when you could. If the event passes without being a crisis...there is nothing to stop you from turning around and going home. Don't worry about feeling foolish for running if a feared crisis didn't materialize...better safe than sorry.