Visual Description: Washington Irving inspiration.
TREPU = ERUPT, MASHE = SHAME, ORIHAD = HAIRDO, FIRDAT = ADRIFT — Giving us: EUSHEHDOADT
Clue/Question: Sleep hollow’s Horseman needed to get to New York City, so he – – –
Answer: TOOK THE METRO NORTH TRAIN FROM TARRYTOWN
Just Kidding! The Answer is: HEADED SOUTH
(But, that’s how he might get there today! But of course, there is nothing punny about taking the Metro North. Irony, yes. But, punny, no. All of today’s clue words are old favorites again. But also, all of the jumbles came up as new. I was thrown for a few seconds by both “mashe” and “firdat”. Great jumbles! It’s been a while since we’ve seen “hairdo”. The answer letter layout was a marvelous jumble. If you’re not familiar with where Sleepy Hollow is, I’m sure this might have been a struggle to answer. Jeff’s got a great sense of humor. Ol’ Ichabod was a teacher, so he shows him standing at the gate of the Sleepy Hollow Middle School. I guess he’s made peace with that nasty Headless Horseman. Be well and do good, friends.) — YUR
Unclerave's Wordy Weblog 
I love this answer! I fumbled it around despite knowing the geography relationship here, despite instantly realizing the first word would be a verb ending in -ED, and despite an obvious clue word noun to go before the -ED. I couldn’t see the compass word until only its five letters remained. Fun one. Well done guys!
You’re a very deep thinker, David! That’s usually a good thing. But, sometimes you’ve just got to go with your gut. Mine is rather large – my gut – so I don’t have to think too hard.
— YUR 😉
Sames here, David! I noted all the same things you mentioned, and dug up all the Sleepy Hollow info I could remember…but still, no light bulb moment…but finallyyyyy……eureka! Great puzzle, solution, artwork! PS, UR, Wilco played in Indy last night! =)
Very cool, jenn! Maybe, our buddy Jeff was there. He’s a diehard fan! — YUR
You’re right, unclerave, it’s easy to err on the side of overthinking the Bonus Answer, and I am guilty of that many of those times when I’m not seeing it right away.
We all fall into that trap, from time to time, David. Sometimes these are ultra-easy, and other times they’re a bit difficult. I love to be challenged, but I have to remind myself that the guys are producing these for a wider audience. At times, I can be a little too critical, and I have to remind myself that it’s just a puzzle/game.
— YUR