I've only met him once, on the road near Markarth I think it was, but it was so long ago. It was before I knew of him, and I thought he was an unfriendly ghost, and immediately attacked him, but when he just rode right past me, I just left him alone. I should have followed him =(

i've seen another ghost also along my travels.he/she wasn't either headless or on a horse.i tried chasing them,but they just disappeared.

http://cloud.steampowered.com/ugc/613846549749904880/55F7A9315FB54DA5A7577D3AC3860B7A505E7FAC/! I happened upon him this way, no dragons or any enemies near.

Really? I see him all the time.

The poor thing!
I would probably not stop laughing if I ever would see that in game.

He is an Easter Egg, and this thread is in the wrong section.

He can be seen running along the roads near whiterun on horse from time to time. His purpose is to lead you into an ambush.

I've yet to see him and I don't use fast travel that much

How is this in the wrong section?

The first time I came across him, I was near the Thalmor Embassy. The second time I saw him was close to the first not long afterwards

I saw him for the first time today in Labyrinthian, after 54 levels with my Nord male and 57 with my Altmer female. I had just finished a certain area there, and it was around midnight. He came trotting through and up the hill. Shadowmere was in the wrong place, so I chased him on foot until my stamina started to get low. Then I used the Slow Time shout and caught up to him. In slo-mo, "Talk to Headless Horseman" popped up when I got very near. He wouldn't talk to me though. After that, I was able to keep up with him on foot without trouble. He got to Hamvir's Rest, then unceremoniously disappeared. No SFX or anything. He just popped off the screen. Weird.

i just saw the headless horseman also,not for the first time mind you (have just restarted with a new character she's currently level 4).was returning to dragonsreach when i saw him in the distance.i chased after him as best i could.i followed him to a fort where the bandits were shooting arrows at him.he them proceeded to fly up in the air and away (disappeared) as the sun was coming up.

Just met him outside Rorikstead last night!! He was coming over the mountain on a small trail and I followed him all the way to his final destination (Hamvir's Rest), where he simply disappeared, and I got attacked by skeletons. Thanks headless horseman. No, really, thanks.

Along the way he made a stop at Fort Greymoor. He even went off the road a bit to go all the way up to the gate. Makes me think it was one of his old stomping grounds. Maybe he was a commander there, or something. He wears Steel Plate Armor, so he must've been an officer of some sort. And his name is obviously Hamvir, cause he's buried at...Hamvir's Rest.

At least that's what he is to me now =)