Aarakocra in 5e have a flying speed of 50 feet. But there doesn't seem to have a whole lot of other specifications on flight.
How can I give characters challenges when many of them are avoided through flight? For instance:
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An inescapable pit is made escapable with flight.
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Scaling a tower or mountain is made simple by flying to the top.
How can I keep challenges like this without getting rid of their flight all together?
Best Answer
There are ways to prevent easy flight -- Strong Wind (DMG p.110) is the most obvious -- but maybe the more important response to your question is to ask:
Why does flying need to be countered or prevented?
Early-access flight isn't unique to aarakocra. Many spellcasters can cast Levitate at 3rd level and Fly by 5th, and Druids can wildshape into birds at 8th level. A number of classes, races, or items can provide short-range teleportation at low levels, which brings up many of the same questions. If your story depends on the heroes being unable to access specific physical locations, you're going to have a lot more problems than one guy with wings.
But I think you'll find that it doesn't happen as often as you fear.
Unless the entire party can fly or teleport, they can't really bypass most situations by just flying over it. Okay, one guy got over the castle wall -- what now? Either he's alone in enemy territory and has to find the drawbridge controls, which is a nice little adventure beat of its own, or he throws a rope down and everyone else has to climb up, which is making rolls to accomplish a task (and not real different from the barbarian climbing the wall first, or the rogue throwing a grappling hook up). And if the party spends resources (spells, items, etc) to bypass a problem, then what's wrong with that? They're correctly using their characters' abilities to face challenges.
Some of your questions make me a little worried. What is an 'inescapable pit', exactly? Is it immune to being climbed (how?), grappling-hooked out of, and so on? Do you really want that in your game? If you feel you need to continually put 'no return past this point' signs in front of your players, you might be railroading them too much. They should be moving forward because they want to finish the job, not because it's impossible to walk any other direction.