Originally Posted by MN Tigerstripes
I don't ride my horse onto their property to ask. Clean yourself up, put on some decent clothes (not dressy, but clean and well fitting) and drive your car down to ask if it's ok.
Tell them who wants to ride, your best bet is just yourself, most landowners don't want randoms coming on their property. At first ask for a specific date/time, you have a much better chance of a onetime yes than a blanket yes. At least at first, after the landowner gets to know you a little better they may just offer for you to ride whenever you'd like.
To up your chances of getting free rein to ride whenever you'd like be respectful of their property. Don't ask to ride when it's wet, clean up after yourself and your horse (yes this includes manure if its on a yard or driveway), be SAFE (landowners worry about liability a lot), if they have small children offer a pony ride. Basically be nice, respectful, and develop a relationship with them.
ITA -- or, in our case, get to know the ONE neighbor who knows everyone else and already has done all this, invites you join HIS riding group and then introduces you to these people and facilitates the extension of such permissions. Treat their property as you would want a "guest" to treat your's and you are more likely to be well -received/allowed back. Many of the people who allow our group (we don't always ride in one group - just using that to refer to the overall members of our bunch who often ride in ones or twos and sometimes as a whole group) actually appreciate having extra eyes and ears on their property who can report things that are amiss (ie broken fences, noticing activity from those NOT supposed to be there, etc).
If you aren't sure who owns a particular piece of property (very common where we are at because many of the larger farming families own parcels scattered about), try talking with your neighbors, etc to figure out just who it is so that you can contact them.