#wilderwest lore
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Hiccup the First's Capital City of the Wilderwest (HTTYD)
You know, I got to thinking:
We know that Grimbeard disliked being confined to Berk, viewing it as not a PROPER PLACE for a KING, so he built the Great City of Tomorrow.
But what was the place Hiccup the First and the other Kings made their capital? Was it Berk? Or was it the Mainland but then it later became Berk?
My headcanon was that after becoming King, Hiccup the First rallied his Tribe and routed the Uglithugs out of the Mainland, which had been the Hooligans' original home before they got kicked out by them just after Hiccup was born. And a plausible theory being that after Hiccup died, or even perhaps after his son's reign, the Uglithugs took the Mainland back, forcing later Kings to rule from Berk.
What do you guys think? Plausible?
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thewolfwarriors · 1 year ago
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All these Im already working on but just kinda been lost on what to finish lately.
Feel free to make suggestions too
Elaborations below:
Wolf Warrior Guide - Been working on one for Foam Rage lately! Its the disease that wiped most of them out and dispersed them around the Wilderwest
(Once enough lore and guides are out together, Id like to make something about people making their own)
Gay Art - Been thinking of Keensharp x Thuggory art 👉👈 would be sfw of course. Theres also my first gay OC i ever made who was Alvins son! May make a ref for him
Wolf Warrior Art - OCs and Madguts being cute or doing stuff. Mewgull lore would also be fun. I just dont think people really care about my personal works and thats TOTALLY FINE. I do it for me! Ive been doing this HTTYD fan fiction for 16 years now. Im just still too shy to really post anything and need some encouragement. Asfeqektnwlwk
Gumboil - gumboil yeah as always the boil boi
Fan Fiction - Ive written several of these and just finish them like 76% and stop. I do wanna work on them again tho!! They're short little snippet stories. These will contain my OCs
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companion-of-the-dragonmark · 3 months ago
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When Was the First Kingdom of the Wilderwest Built? (HTTYD Books)
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Hello, my fellow Dragonmarkers! It's been awhile! As promised, here's the article concerning the plausible timeline of the Kingdom of the Wilderwest. This article was actually a very old one of mine that I had written during this month in 2018. Why didn't I post it on here? Because I wasn't on Tumblr until 2020. And by then, I had forgotten to post this on here. Whoops. Teehee. 😜
When did Hiccup the First end the First Human-Dragon War and built the First Kingdom of the Wilderwest?
Many fans just go with what Wodensfang says in Book 11, supporting the 1000-Year Dynasty mentioned in Book 11 rather than the 500-700-Year Dynasty suggested in Book 9. In fact, it's everywhere in the HTTYD Wiki. I guess it's because fans view Book 11 to be more accurate because it's a later book? I don't know; maybe I'm thinking too hard about this.
But I want to talk through this and thoroughly go through the pros and cons of both sides of the argument and do this right. I'd love to know what you guys think about this.
Anyway, on to the topic!  
Possible Contradiction?:
In the First Book — the Book that we're all familiar with — in Chapter 6, Page 68, says that:
"The Dragon (speaking of the Green Death) had crawled down into the depths of the ocean and had gone into a Sleep Coma. Dragons can stay in this suspended state for eternity, half-dead, half-alive, buried under fathom after fathom of icy-cold seawater. Not a muscle of this particular Dragon had moved for six or seven centuries."
Wodensfang's account of Hiccup the First in Book 9 "How to Steal a Dragon's Sword", on Chapter 12, Page 203, seems to probably confirm this when he says: "Five or six centuries ago, when I was young, it was a very dark age, and the dragons and humans were at war."
He goes on further explanation in Page 208 concerning the Green Death: "...Merciless flew to the north, and to the Open Sea. He lived so long a loner that perhaps over the centuries he forgot his youth as leader of a dragon army and became quite an ordinary killer. Rumor was that several hundred years later, he was known only as the Green Death, one of the many monsters that terrorize the Deep Sea."
So you're probably saying, "Great! There it is! There's your answer! It was 600-700 years ago! Problem solved, right?"
Wrong.
In Book 11 "How to Betray a Dragon's Hero", on Chapter 6, Page 98, Wodensfang tells the story of how the Dragonmark came to be, as well as a more detailed history of the Kingdom of the Wilderwest and the story of Grimbeard the Ghastly as a boy, and how he changed the Mark. 
He says at the beginning of the story: "Once upon a time, Hiccup, a thousand or so years ago, when I was young and about the size of a Saber-Toothed Driver Dragon, I met your ancestor, Hiccup Horrendous Haddock the First, and I gave him the Dragon Jewel and trusted him with the Jewel's Secret."
In Page 100, Wodensfang repeats this by saying: "For over a thousand years, it seemed like I had made the right decision to entrust the Secret of the Dragon Jewel to the humans."
I know right? I'm as confused as you are! Didn't he say in Book 9 that it was "five or six centuries ago"? Maybe even SEVEN centuries ago? Why the change? Did he suddenly get the Dragon equivalent of memory loss due to old age? Does he not know how to count?
Here's the confusing thing: if he was rounding, this might explain it. But the thing is that you can do it with small numbers, but as the number gets bigger, you can't round up in great jumps.
(Warning: Math Ahead!)
For example, say that the number is 8, you round it up to 10 (in certain circumstances) because 8 is closer to 10 than 5. However, if it's 6, then you have to round down to 5 because 6 is closer to 5. The only time that it doesn't is when you're rounding up in percentages (55.678594375 would be 56, for example).
You can't round up to 1000 years from 600, or even 700. That's too high of a jump. Especially when you're telling a historical account. For one thing, it's inaccurate, and for another, it's lazy. And it'll spread lots of confusion.
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A Roman Piece to a Nordic Puzzle | The Hint's in the Roman Numerals: 
So then, which is it? Was the Kingdom of the Wilderwest built 600-700 years ago or 1000-odd years ago? 
First off, allow me to redirect your attention once more to the references concerning the Green Death (also known as Merciless):
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The Green Death Takes His Tea by Crownflame on DeviantArt
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"The Dragon (speaking of the Green Death) had crawled down into the depths of the ocean and had gone into a Sleep Coma. Dragons can stay in this suspended state for eternity, half-dead, half-alive, buried under fathom after fathom of icy-cold seawater. Not a muscle of this particular Dragon had moved for six or seven centuries." 
And this one:
  ". . .Merciless flew to the north, and to the Open Sea. He lived so long a loner that perhaps over the centuries he forgot his youth as leader of a dragon army and became quite an ordinary killer. Rumor was that several hundred years later, he was known only as the Green Death, one of the many monsters that terrorize the Deep Sea." 
According to these two quotes concerning the Dragon Merciless, it would appear that the events were about roughly 600 years ago. The problem is that the first quote says he had been in a Sleep Coma for six or seven centuries. I don't know about you, but that doesn't seem like a lot of time to me for him to have forgotten his past and about his nemesis Hiccup. It sounds like in the latter quote, Merciless lived and journeyed alone for a long time — about 100-200 years or more — before he fell into a Sleep Coma.
What might help support this is the mention of what he had eaten in Book 1, Page 129: "He was awake now, and he had coughed up the last thing he had eaten, the Eagle Standard of the Eighth Legion, with its pathetic ribbons still flying bravely."
Now, yes, the HTTYD books are exaggeratory and any historical references are "purely coincidental," and that the Roman Dragonrustlers were about during Hiccup the Third's time (but after Book 3 was said to have fled back to Rome — which is inaccurate because Hiccup's time was during the Viking Age, over 300 years after the fall of the Roman Empire. However, I have a theory that'll explain that in the future). 
But what if we DID get historical here? According to history, the only 8th Legion in Roman history was the Legio VIII Augusta, one of the oldest Roman legions in Rome's history (along with the Legio VI Feratta, Legio VII Claudia, and the (in)famous Legio IX Hispana). They were stationed in Gaul (modern France) near the modern-day Strasbourg area (called Argentoratum in Roman times). It was founded in 65 BC by Julius Caesar during the Gaul Wars. It continued service presumedly until either before or until the Fall of Rome (400-500 AD). 
Of course, since it continued service until that time period, then it's impossible for the Green Death to have eaten the Legion, right?
As Old Wrinkly used to say: "It's not im-POSSIBLE, only im-PROBABLE. The only thing that limits us are the limits to our imaginations." 
So, taking this sagely advice, let's think about this carefully.
According to Roman history, the Eighth Legion was disbanded during the first of Rome's Civil Wars (called Caesar's Civil War and the conflict was between Caesar and Scipio) soon after the Battle and Siege of Thapsus (modern-day Tunisia) in 46 BC for unknown reasons. It was reconstituted in 44 BC by Caesar's adopted son Augustus for Caesar's veterans who had loyally served him and helped him defeat Mark Antony and gain power as Rome's first Emperor.
So basically, there's a two-year gap between the disbandment and the reinstation of the Eighth Legion, which means that Merciless could've easily have eaten the Legion during that time and nobody would've been the wiser, and when Augustus reinstated the Legion two years later, he filled the ranks with other veterans who had served Caesar and Augustus.
What do you think? Plausible?
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Possible Connection to Dragon-Aging and Dates in the Book of Dragons:
Now, in Book 1, in the back of the How to Train Your Dragon book that Hiccup reads (similar to the Book of Dragons in the film) in Chapter 4 on Page 53-58, it says that the last stamped due-date was on "16 May 866 AD". The first and second due-dates stamped on there before that were "10 June 789 AD" and "9 April 835 AD".
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However, there's no mention of when that book was borrowed, or when it was returned, or the gap between the date and when Gobber the Belch had burgled it from the Meathead "Public" Library. The Hooligans seemed to have had the book for a while. So the current date of the time of Hiccup's first memoir could be anywhere from 866-900 AD — if not later! 
Suffering Scallops, it could even be in the 1000s AD!!! In Book 7, Hiccup writes in his epilogue that: "Now I am an old, old man, and the world that I created has no need for dragons. They have retreated from the civilization that I brought, along with the wolves, and the Berserks, and the monsters of my childhood."
In 1015 AD, Berserkers were outlawed, and the practice of "going berserk" as a profession and the rituals involving their cults were forbidden until by the turn of the 12th century, Berserkers had all but disappeared from human history. The end of the Viking Age was considered to be between 1066-1100 AD, so, scallops, Hiccup could very well have lived during this time.
(This could explain the crossbows in the TV series, as they were beginning to show up around this time, as well as Hiccup's quote in the first film: "300 years and I'm the first Viking who wouldn't kill a dragon!") 
And, in Book 12, Hiccup also explains in his epilogue that Sea-Dragons like Toothless can live for thousands of years, so maybe 1000-year period might be correct? There's no mention about the other sea dragons, apparently, so I guess they don't live nearly as long?
The problem is the period of growth in the Sea-Dragons. Wodensfang was probably of-age by the time he meets Hiccup the First, and he was "the size of a Saber-Toothed Driver Dragon" then. Then, as the decades and centuries went by and the Kingdom prospered, he grew to be "as large as a mountain". Then he says that hundreds of years ago, he began to "shrink in old age", as Sea-Dragons are small in young and old ages, but in adult stages they're colossal, until he shrunk to the "size of a large Viking hunting dog (probably a Norwegian Elkhound, which lived during this time and was used mainly as a guard and hunting dog)" during the time of Grimbeard the Ghastly. By Hiccup the Third's time a hundred years later, he shrunk to the size of Toothless.
Furious was still considered a baby during Hiccup the Second's time, but grew to be the size of a small elephant. Then 100 years later, he became the size of a mountain, when it doesn't seem that Wodensfang grew that big that quickly (though, to be fair, the Berserks had been feeding him well with human sacrifices for the past 100 years, among other foods, so he probably grew to be that big because of it.) He must've had an early growth spurt. lol 😂
That being said, the reason Furious and Wodensfang have different growing speeds may be likely due to Furious having been fed well since his hatchling days. Whereas it's hinted by Wodensfang himself that he's had a difficult life in his younger days, which is one of the reasons he joins Merciless' rebellion against the Vikings. So the struggle for food could've stunted his growth until he met Hiccup the First later on, at which point he grew faster as more food was available.
Meanwhile, there's Toothless, who's a baby, and has been the size of Wodensfang since the first book, and, according to Hiccup in his epilogue in Book 12, hasn't really grown up at all despite it being 62 years since the events of Book 12 (which if Hiccup was 10-11 when he got Toothless in Book 1, this would make Toothless 65-66 years old by Hiccup's death) and is still able to sleep on his chest. 
He must be a late bloomer. lol 😂
Then there's the Green Death — or Merciless — to consider. While he was Furious's size during Hiccup the First's time, and was considered to be a young dragon, then several centuries later, if not more, when he meets Hiccup the Third, he's still the same size! Do Sleep Comas delay aging and growth or something?
So basically we have FOUR Sea-Dragons who grow and age at various speeds! So I don't think we can glean anything from this.
So . . . 1000 years or 600-700 years? Honestly, I seem to get more confused the further I try to explain it! I hope you're having better luck keeping up than I am at the moment! lol 😂
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Time For a Little More Math! (cue the groans!):
Okay, I'm going to do a little more math. To be honest, graphs, charts, and basic math is the only math I love. If you don't like it, then skip if you'd like, though you'll miss out on the cool part. 😉🧐
I've done the calculations and I'll do my best with it. If there are any mistakes, please let me know and I'll correct them. 
I'll be using current time from 866-1100 AD and then add the date to when the Kingdom of the Wilderwest could've been established in Hiccup the First's time. 
I will be using the terms CTP (Current Time Period) and DFP (Dynasty Foundation Period) to avoid confusion.
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Whew! Okay! Now that THAT'S done and over with, let's get to the average ages of the Kings of the Wilderwest to further prove (hopefully) which date it might've been. 
I've organized it into different sections. Before Hiccup the Third, there were 12 Kings of the Wilderwest. So I'll divide the number of years that the Dynasty could've lasted to the number of Kings to get the average lifespan that each of the Kings have to be in order for this to become plausible.
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Now granted, some of these Kings could've died young (20s-30s), or very old, or in their middle-ages (pun not intended). This is the AVERAGE lifespan for each king -- not a literal statistic for each and every King. 
Unless, of course, if we were fanciful people, we might've theorized that there's some sort of magic spell in the Dragon Jewel that Wodensfang didn't mention that causes all of the Twelve Kings to die at the same age. 
In that case, if true, and if every King DOES INDEED die at the same age, then since Hiccup the Third dies at the age of 75/76, it would've been 900 years since the foundation of the Kingdom of the Wilderwest since every King would've died at the same age that Hiccup had died.
But we're not fanciful people . . . and that would be ridiculous. lol 😜
However, you're probably noticing that there are no 1000 Years among the statistics that I just showed above. That's because I had just remembered that the Kingdom of the Wilderwest collapsed a hundred years before Hiccup the Third's time. Meaning that if the Dynasty and Kingdom lasted for 1000 years, then only 900 years of that has passed as a kingdom.
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Conclusion:
So . . . WHEW! That took a long time to write (5-6 hours, though the time could've been cut in half had I not done the statistics, but then where'd be the fun in that? lol 😜)
I apologize if any of this went over your head or overwhelmed you with informational overload. If it did, then I sympathize because I'm feeling this as well — and I'm WRITING THIS! 
So my conclusion is that, basically speaking, regardless of the Kingdom being anywhere from 600-1000 years old, 100 of those years need to be subtracted since the Kingdom fell apart when Grimbeard dissolved it a hundred years prior to the current events of the Second Dragon War. So, realistically, the Kingdom — and the 12 Kings (including Grimbeard) — lasted around 500-900 years, and when Wodensfang tells Hiccup the Third about the history of the Wilderwest, he includes the 100 years into the timeframe when the Kingdom of the Wilderwest was first founded.
So I guess that, in the end, the actual date and timeline will be left up to the fans to headcanon for themselves.
If you could take anything from this, what would it be?
What current timeline do you think Hiccup the Third could be living in during the Viking Age? 900s? 1000s? 1100?
And how many years do you think that the Kingdom of the Wilderwest was established (including the 100-year gap)? 1000 years? 800? 700? 600? 
Please share your thoughts! I'd LOVE to hear from you!!! ^_^ 
Thank you SO MUCH for taking the time to read this and I am looking forward to reading any theories, corrections, suggestions, discussions, answers, and/or questions you may have. 
I hope this article finds you well, and I hope you have a splendid weekend! 
Long Live the Wilderwest!
— Companion of the Dragonmark
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companion-of-the-dragonmark · 3 months ago
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New HTTYD Article Coming Soon!
Greetings, fellow Dragonmarkers! Just wanted to let you know that I'm currently working on a new article for the HTTYD Books, focusing on the timeline of the books and the Kingdom of the Wilderwest.
Keep an eye out!
Long Live the Wilderwest!
— Companion of the Dragonmark
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companion-of-the-dragonmark · 3 months ago
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Thank you very much! I very much enjoy diving into the lore of the books and come up with some plausible history/backgrounds from it, despite Cressida's fantastical take on it. 😁
And as a history enthusiast, I always try to tie it up with historical events. 🧐🍷
OH! You know, that could very well work, too!! 😮👀 Good thinking. After all, there's nothing to say that it was the Western Empire's 8th Legion. It could've been the Eastern Empire's 8th Legion. 😆 That being said though, the geography doesn't really match. Not unless the Green Death/Merciless traveled to the Mediterranean. But then, that, too, could be plausible. We just simply don't know. Hence, why it's a theory. 😉
Yeah, that's true. And yeah, I always found that annoying. And Cressida, to my annoyance, has never, to this day, given us an explanation for the different growth rates. 😑 Like, help us out here, we're DYING to know! 😫
When Was the First Kingdom of the Wilderwest Built? (HTTYD Books)
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Hello, my fellow Dragonmarkers! It's been awhile! As promised, here's the article concerning the plausible timeline of the Kingdom of the Wilderwest. This article was actually a very old one of mine that I had written during this month in 2018. Why didn't I post it on here? Because I wasn't on Tumblr until 2020. And by then, I had forgotten to post this on here. Whoops. Teehee. 😜
When did Hiccup the First end the First Human-Dragon War and built the First Kingdom of the Wilderwest?
Many fans just go with what Wodensfang says in Book 11, supporting the 1000-Year Dynasty mentioned in Book 11 rather than the 500-700-Year Dynasty suggested in Book 9. In fact, it's everywhere in the HTTYD Wiki. I guess it's because fans view Book 11 to be more accurate because it's a later book? I don't know; maybe I'm thinking too hard about this.
But I want to talk through this and thoroughly go through the pros and cons of both sides of the argument and do this right. I'd love to know what you guys think about this.
Anyway, on to the topic!  
Possible Contradiction?:
In the First Book — the Book that we're all familiar with — in Chapter 6, Page 68, says that:
"The Dragon (speaking of the Green Death) had crawled down into the depths of the ocean and had gone into a Sleep Coma. Dragons can stay in this suspended state for eternity, half-dead, half-alive, buried under fathom after fathom of icy-cold seawater. Not a muscle of this particular Dragon had moved for six or seven centuries."
Wodensfang's account of Hiccup the First in Book 9 "How to Steal a Dragon's Sword", on Chapter 12, Page 203, seems to probably confirm this when he says: "Five or six centuries ago, when I was young, it was a very dark age, and the dragons and humans were at war."
He goes on further explanation in Page 208 concerning the Green Death: "...Merciless flew to the north, and to the Open Sea. He lived so long a loner that perhaps over the centuries he forgot his youth as leader of a dragon army and became quite an ordinary killer. Rumor was that several hundred years later, he was known only as the Green Death, one of the many monsters that terrorize the Deep Sea."
So you're probably saying, "Great! There it is! There's your answer! It was 600-700 years ago! Problem solved, right?"
Wrong.
In Book 11 "How to Betray a Dragon's Hero", on Chapter 6, Page 98, Wodensfang tells the story of how the Dragonmark came to be, as well as a more detailed history of the Kingdom of the Wilderwest and the story of Grimbeard the Ghastly as a boy, and how he changed the Mark. 
He says at the beginning of the story: "Once upon a time, Hiccup, a thousand or so years ago, when I was young and about the size of a Saber-Toothed Driver Dragon, I met your ancestor, Hiccup Horrendous Haddock the First, and I gave him the Dragon Jewel and trusted him with the Jewel's Secret."
In Page 100, Wodensfang repeats this by saying: "For over a thousand years, it seemed like I had made the right decision to entrust the Secret of the Dragon Jewel to the humans."
I know right? I'm as confused as you are! Didn't he say in Book 9 that it was "five or six centuries ago"? Maybe even SEVEN centuries ago? Why the change? Did he suddenly get the Dragon equivalent of memory loss due to old age? Does he not know how to count?
Here's the confusing thing: if he was rounding, this might explain it. But the thing is that you can do it with small numbers, but as the number gets bigger, you can't round up in great jumps.
(Warning: Math Ahead!)
For example, say that the number is 8, you round it up to 10 (in certain circumstances) because 8 is closer to 10 than 5. However, if it's 6, then you have to round down to 5 because 6 is closer to 5. The only time that it doesn't is when you're rounding up in percentages (55.678594375 would be 56, for example).
You can't round up to 1000 years from 600, or even 700. That's too high of a jump. Especially when you're telling a historical account. For one thing, it's inaccurate, and for another, it's lazy. And it'll spread lots of confusion.
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A Roman Piece to a Nordic Puzzle | The Hint's in the Roman Numerals: 
So then, which is it? Was the Kingdom of the Wilderwest built 600-700 years ago or 1000-odd years ago? 
First off, allow me to redirect your attention once more to the references concerning the Green Death (also known as Merciless):
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The Green Death Takes His Tea by Crownflame on DeviantArt
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"The Dragon (speaking of the Green Death) had crawled down into the depths of the ocean and had gone into a Sleep Coma. Dragons can stay in this suspended state for eternity, half-dead, half-alive, buried under fathom after fathom of icy-cold seawater. Not a muscle of this particular Dragon had moved for six or seven centuries." 
And this one:
  ". . .Merciless flew to the north, and to the Open Sea. He lived so long a loner that perhaps over the centuries he forgot his youth as leader of a dragon army and became quite an ordinary killer. Rumor was that several hundred years later, he was known only as the Green Death, one of the many monsters that terrorize the Deep Sea." 
According to these two quotes concerning the Dragon Merciless, it would appear that the events were about roughly 600 years ago. The problem is that the first quote says he had been in a Sleep Coma for six or seven centuries. I don't know about you, but that doesn't seem like a lot of time to me for him to have forgotten his past and about his nemesis Hiccup. It sounds like in the latter quote, Merciless lived and journeyed alone for a long time — about 100-200 years or more — before he fell into a Sleep Coma.
What might help support this is the mention of what he had eaten in Book 1, Page 129: "He was awake now, and he had coughed up the last thing he had eaten, the Eagle Standard of the Eighth Legion, with its pathetic ribbons still flying bravely."
Now, yes, the HTTYD books are exaggeratory and any historical references are "purely coincidental," and that the Roman Dragonrustlers were about during Hiccup the Third's time (but after Book 3 was said to have fled back to Rome — which is inaccurate because Hiccup's time was during the Viking Age, over 300 years after the fall of the Roman Empire. However, I have a theory that'll explain that in the future). 
But what if we DID get historical here? According to history, the only 8th Legion in Roman history was the Legio VIII Augusta, one of the oldest Roman legions in Rome's history (along with the Legio VI Feratta, Legio VII Claudia, and the (in)famous Legio IX Hispana). They were stationed in Gaul (modern France) near the modern-day Strasbourg area (called Argentoratum in Roman times). It was founded in 65 BC by Julius Caesar during the Gaul Wars. It continued service presumedly until either before or until the Fall of Rome (400-500 AD). 
Of course, since it continued service until that time period, then it's impossible for the Green Death to have eaten the Legion, right?
As Old Wrinkly used to say: "It's not im-POSSIBLE, only im-PROBABLE. The only thing that limits us are the limits to our imaginations." 
So, taking this sagely advice, let's think about this carefully.
According to Roman history, the Eighth Legion was disbanded during the first of Rome's Civil Wars (called Caesar's Civil War and the conflict was between Caesar and Scipio) soon after the Battle and Siege of Thapsus (modern-day Tunisia) in 46 BC for unknown reasons. It was reconstituted in 44 BC by Caesar's adopted son Augustus for Caesar's veterans who had loyally served him and helped him defeat Mark Antony and gain power as Rome's first Emperor.
So basically, there's a two-year gap between the disbandment and the reinstation of the Eighth Legion, which means that Merciless could've easily have eaten the Legion during that time and nobody would've been the wiser, and when Augustus reinstated the Legion two years later, he filled the ranks with other veterans who had served Caesar and Augustus.
What do you think? Plausible?
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Possible Connection to Dragon-Aging and Dates in the Book of Dragons:
Now, in Book 1, in the back of the How to Train Your Dragon book that Hiccup reads (similar to the Book of Dragons in the film) in Chapter 4 on Page 53-58, it says that the last stamped due-date was on "16 May 866 AD". The first and second due-dates stamped on there before that were "10 June 789 AD" and "9 April 835 AD".
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However, there's no mention of when that book was borrowed, or when it was returned, or the gap between the date and when Gobber the Belch had burgled it from the Meathead "Public" Library. The Hooligans seemed to have had the book for a while. So the current date of the time of Hiccup's first memoir could be anywhere from 866-900 AD — if not later! 
Suffering Scallops, it could even be in the 1000s AD!!! In Book 7, Hiccup writes in his epilogue that: "Now I am an old, old man, and the world that I created has no need for dragons. They have retreated from the civilization that I brought, along with the wolves, and the Berserks, and the monsters of my childhood."
In 1015 AD, Berserkers were outlawed, and the practice of "going berserk" as a profession and the rituals involving their cults were forbidden until by the turn of the 12th century, Berserkers had all but disappeared from human history. The end of the Viking Age was considered to be between 1066-1100 AD, so, scallops, Hiccup could very well have lived during this time.
(This could explain the crossbows in the TV series, as they were beginning to show up around this time, as well as Hiccup's quote in the first film: "300 years and I'm the first Viking who wouldn't kill a dragon!") 
And, in Book 12, Hiccup also explains in his epilogue that Sea-Dragons like Toothless can live for thousands of years, so maybe 1000-year period might be correct? There's no mention about the other sea dragons, apparently, so I guess they don't live nearly as long?
The problem is the period of growth in the Sea-Dragons. Wodensfang was probably of-age by the time he meets Hiccup the First, and he was "the size of a Saber-Toothed Driver Dragon" then. Then, as the decades and centuries went by and the Kingdom prospered, he grew to be "as large as a mountain". Then he says that hundreds of years ago, he began to "shrink in old age", as Sea-Dragons are small in young and old ages, but in adult stages they're colossal, until he shrunk to the "size of a large Viking hunting dog (probably a Norwegian Elkhound, which lived during this time and was used mainly as a guard and hunting dog)" during the time of Grimbeard the Ghastly. By Hiccup the Third's time a hundred years later, he shrunk to the size of Toothless.
Furious was still considered a baby during Hiccup the Second's time, but grew to be the size of a small elephant. Then 100 years later, he became the size of a mountain, when it doesn't seem that Wodensfang grew that big that quickly (though, to be fair, the Berserks had been feeding him well with human sacrifices for the past 100 years, among other foods, so he probably grew to be that big because of it.) He must've had an early growth spurt. lol 😂
That being said, the reason Furious and Wodensfang have different growing speeds may be likely due to Furious having been fed well since his hatchling days. Whereas it's hinted by Wodensfang himself that he's had a difficult life in his younger days, which is one of the reasons he joins Merciless' rebellion against the Vikings. So the struggle for food could've stunted his growth until he met Hiccup the First later on, at which point he grew faster as more food was available.
Meanwhile, there's Toothless, who's a baby, and has been the size of Wodensfang since the first book, and, according to Hiccup in his epilogue in Book 12, hasn't really grown up at all despite it being 62 years since the events of Book 12 (which if Hiccup was 10-11 when he got Toothless in Book 1, this would make Toothless 65-66 years old by Hiccup's death) and is still able to sleep on his chest. 
He must be a late bloomer. lol 😂
Then there's the Green Death — or Merciless — to consider. While he was Furious's size during Hiccup the First's time, and was considered to be a young dragon, then several centuries later, if not more, when he meets Hiccup the Third, he's still the same size! Do Sleep Comas delay aging and growth or something?
So basically we have FOUR Sea-Dragons who grow and age at various speeds! So I don't think we can glean anything from this.
So . . . 1000 years or 600-700 years? Honestly, I seem to get more confused the further I try to explain it! I hope you're having better luck keeping up than I am at the moment! lol 😂
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Time For a Little More Math! (cue the groans!):
Okay, I'm going to do a little more math. To be honest, graphs, charts, and basic math is the only math I love. If you don't like it, then skip if you'd like, though you'll miss out on the cool part. 😉🧐
I've done the calculations and I'll do my best with it. If there are any mistakes, please let me know and I'll correct them. 
I'll be using current time from 866-1100 AD and then add the date to when the Kingdom of the Wilderwest could've been established in Hiccup the First's time. 
I will be using the terms CTP (Current Time Period) and DFP (Dynasty Foundation Period) to avoid confusion.
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Whew! Okay! Now that THAT'S done and over with, let's get to the average ages of the Kings of the Wilderwest to further prove (hopefully) which date it might've been. 
I've organized it into different sections. Before Hiccup the Third, there were 12 Kings of the Wilderwest. So I'll divide the number of years that the Dynasty could've lasted to the number of Kings to get the average lifespan that each of the Kings have to be in order for this to become plausible.
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Now granted, some of these Kings could've died young (20s-30s), or very old, or in their middle-ages (pun not intended). This is the AVERAGE lifespan for each king -- not a literal statistic for each and every King. 
Unless, of course, if we were fanciful people, we might've theorized that there's some sort of magic spell in the Dragon Jewel that Wodensfang didn't mention that causes all of the Twelve Kings to die at the same age. 
In that case, if true, and if every King DOES INDEED die at the same age, then since Hiccup the Third dies at the age of 75/76, it would've been 900 years since the foundation of the Kingdom of the Wilderwest since every King would've died at the same age that Hiccup had died.
But we're not fanciful people . . . and that would be ridiculous. lol 😜
However, you're probably noticing that there are no 1000 Years among the statistics that I just showed above. That's because I had just remembered that the Kingdom of the Wilderwest collapsed a hundred years before Hiccup the Third's time. Meaning that if the Dynasty and Kingdom lasted for 1000 years, then only 900 years of that has passed as a kingdom.
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Conclusion:
So . . . WHEW! That took a long time to write (5-6 hours, though the time could've been cut in half had I not done the statistics, but then where'd be the fun in that? lol 😜)
I apologize if any of this went over your head or overwhelmed you with informational overload. If it did, then I sympathize because I'm feeling this as well — and I'm WRITING THIS! 
So my conclusion is that, basically speaking, regardless of the Kingdom being anywhere from 600-1000 years old, 100 of those years need to be subtracted since the Kingdom fell apart when Grimbeard dissolved it a hundred years prior to the current events of the Second Dragon War. So, realistically, the Kingdom — and the 12 Kings (including Grimbeard) — lasted around 500-900 years, and when Wodensfang tells Hiccup the Third about the history of the Wilderwest, he includes the 100 years into the timeframe when the Kingdom of the Wilderwest was first founded.
So I guess that, in the end, the actual date and timeline will be left up to the fans to headcanon for themselves.
If you could take anything from this, what would it be?
What current timeline do you think Hiccup the Third could be living in during the Viking Age? 900s? 1000s? 1100?
And how many years do you think that the Kingdom of the Wilderwest was established (including the 100-year gap)? 1000 years? 800? 700? 600? 
Please share your thoughts! I'd LOVE to hear from you!!! ^_^ 
Thank you SO MUCH for taking the time to read this and I am looking forward to reading any theories, corrections, suggestions, discussions, answers, and/or questions you may have. 
I hope this article finds you well, and I hope you have a splendid weekend! 
Long Live the Wilderwest!
— Companion of the Dragonmark
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