"Where is the best place to hunt for truly difficult spelling words?"
Why not use the same tome that gets scoured every year by the cruelest word judges in the world — Websters Unabridged Dictionary. For the uninitiated, that's the official spelling dictionary used in Scripps National Spelling Bee.
And that's what I've done on this page. In fact, each and every one of these words has actually appeared at least once in a round of Scripps National Spelling Bee. For some of the words, I've included a spelling bee moment from the informative book, American Bee. Each one of these snippets contains a friendly word of warning for future Bee hopefuls.
NOTE — You may find an alternative spelling of a word in your own preferred dictionary, but it is more likely that you won't find it listed at all! They are not just difficult spelling words. They are pretty darn obscure ;-)
APHAERETIC
adj. Relating to the omission of the first letter of a word (e.g. 'round' for 'around').
This was the word bullet that shot down Scott Firebaugh in the 2011 AARP Spelling Bee. Firebaugh was the 2010 AARP Champ, but was relegated to 3rd place in the 2011 event after misspelling this word as APHORETIC*. I was following the event at the time, and that is exactly how I spelled it!
BOEOTIA — bē.ō.sh(ē).ə
n. A district in Ancient Greece.
BORBORYGMUS — bȯr.bə.rig.məs
n. A rumbling of the intestines.
"Then again, the spelling of even apparently rule-bound words from Latin and Greek antiquity must be handled with care. A speller at the 2003 National Bee, Michael Martinez, from New Mexico, learned this the hard way. He was given the lovely borborygmus... He spelled it, reasonably, using the Latinate suffix ous meaning 'full of,' as borborygmous - which is precisely how the word sounds. And then, of course, he was sent offstage. Speller beware."
DAGUERREOTYPE — də.ge.rō.tīp
n. An early photographic technology.
ORFEVRERIE — ȯr.fe.vrə.rē
n. Gold or silver jewelry.
"The words are now torturous. Aliya Deri gets orfevrerie, a conflagration of French and English history that resembles the Battle of Hastings, yet she greets it with an unabashed smile. Her French classes allow her to slay the word with comparative ease. She's looking like she could take the trophy."
PRAIRILLON — prā.ril.yən
n. A small prairie.
"He was dealt the word prairillon, a French word referring to a small prairie. He attempted a characteristically French spelling of prerillion, a misspelling that put Jody-Anne in position to win."
PSITTACINE — si.tə.sīn
adj. Relating to a particular family of parrots.
RIJSTTAFEL — rīs.tä.fəl
n. An Indonesian rice dish.
SCHEHERAZADIAN — shə.her.ə.zä.dē.ən
adj. Strangely fabulous.
"Ashkay, in an uncharacteristic gesture, pauses in spelling scheherazadian. He masters the first syllable then stares off to his left. The audience holds its breath. Rarely has a full ballroom been so still. He announces that he will start over... When he starts again, he announces each letter with an even cadence, like a drummer at a solemn occasion slowly tapping out a somber beat. He's correct. The crowd breaks into applause, in response to which Akshay slowly blinks and mummy-walks back to his seat."
n. The edible corm of the 'chestnutty' Iridaceae family of plants.
David Riddle, multiple adult spelling bee champion, astounds the audience by spelling this word correctly and, in the process, winning the Williamsburg Adult Spelling Bee. The word was voted the hardest word ever spelled in the six-year history of the bee!
VITROPHYRE — vi.trə.fī(ə)r
n. A type of glassy rock.
VORAGO — və.rā.gō
n. A deep chasm.
"Kerry, however, runs into a wall. Her word is vorago. But it doesn't sound like vorago; it sounds like varago, or possibly verago, or, maybe, vurago. Formed from a Latin root, the word means an engulfing chasm; an abyss. And that's exactly what Kerry looks into as she considers the word. She doesn't know it, and she's going to have to guess."
Had enough? What?! You mean you're hungry for...
More Difficult Spelling Words?
Well, since I've just been talking about the National Spelling Bee, here's another nasty spelling list. Below are all the words that have won the Scripps Bee for the last 20 years. In other words, each of the words in this list was the final word that was correctly spelled by the last speller standing after months of grueling playoffs!
You can find the meaning and pronunciation of each of these words, along with thousands of other ridiculously difficult spelling words, in Websters Unabridged Dictionary.
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. For the uninitiated, that's the official spelling dictionary used in Scripps National Spelling Bee. 
