There needs to be a naval battle!

@kleptomage  
Indeed, Equestria is a complete cluster fuck in both Technology and time period.

@Navanastra  
It truly is a bizarre design for a cargo ship. There are good reasons historical ships didn’t look like this.
 
Equestria’s technology level has always been schizophrenic. Generally it’s about early Industrial era but then they have things like chainsaws and hydroelectric dams.

Look at the size of these things, and with those dinky little sails they have i wouldn’t be surprise if these ships are as movable and nimble as a man trying to push a boulder. Especially if they are loaded.
 
Also really weird mix going on here, a 1930s/1940 style New York but the harbor is filled with like 16th or 17th century cargo ships. This world makes no sense.

Thats right all the slave sheep get off the boat and into the pens with you. next it will be sheering them and hot box in no time. i mean only the black ones of course

@Vree  
We saw a yacht in the “Raity takes Manehattan”episode but it looked like your standerd looking modern yacht. I like the old timey yet still decidedly pony look of these ships,helps give more flavor to the ponyverse than any modern looking ship would.

You know what? I think this is actually the first time we saw what MLP ships look like.

@Ebalosus  
Seemingly, as suggested by another comment, sheep are being moved to the north where Manehatten is located to get their sheared wool closer to the seamstresses who manufacture the materials for the armour worn by the enlisted fighting very near that region: North Equestria.
 
Nothing fully indicated Sombra’s Crystal Empire is winning because part of the country has been conquered. It’s possible Equestria was taken off-guard and the war could be won in four, five years just as ours was on Earth.
 
If I find out I’ve been the only individual referencing WWII this whole time, I’m going to kill myself. XD

@Darth Sonic  
While the ponies may have some flying machines it’s unlikely those helicopters in the show can be suitable for anything other than recon, which a Pegasus could probably do easier and faster or maybe transporting suplies maybe.  
I’m not sure if they really have any wing based aircraft but the only other flying machine I see that would be effective would be the airships which would be invaluable as transports or bombing ships. Sombra didn’t seem to have any Pegasus of his own with his crystal pony army so they could probably only take out the airships with some sort of magic which Equestria could possibly counter.
 
It’s difficult to think how qudrapeds with magic as a resource and no guns would fight a large scale war. The supposed peaceful nature of Equestria probably meant at the beginning of the war, Equestria was not at all prepared for total war. It’s doubtful that was Celestias plan to deal with Sombra Though even in the prime timeline she seemed surprised by the Empires resurgence.
 
From we see from the show Equestria has seemed to to modeled into a total war economy and if those circle like things on the pie sisters uniforms really were hydraulics akin to an “exo suit” as some theorize then it would suggest there has been a significant progression in technology or perhaps the technology has always existed and we just never saw it. One could only speculate how magic could effect the war though it’s possible tactics similar to WW1 might soon appear such as weaponized gas, long range artillery and possibly even trench warfare and tanks.

@Hollow_Shades_resident  
Oh yeah, they do! So that makes this one of those awkward “bombing runs and swords” universes? How do yo even manage a battlefield like that?

>Checks map of Equestria
 
Uh, isn’t the whole Crystal War a case of land war in asia type situation?

Would be cool to see a Taipan! style kind of trading game in this timeline…

@Manual_Monaro  
That thing has got to be the least utilitarian truck in the history of motor vehicles, but still, if it showed up in the show I wouldn’t complain. Much.
 
@Hollow_Shades_resident  
Yep, and Jet Set’s name and cutie mark indicate that they also have jet planes. Seems like Equestria has reasonably modern vehicles, even though we don’t see them that often.

@FSin  
A sailing boat, modern boat with a chimney and a tourist yacht were all in Rarity Takes Manehattan.

@Background Pony #ACFD  
Plus they have airships and helicopters in the show.

I love those ships! And is that figurehead a sea pony? :o
 
@Background Pony #ACFD  
Well, Applejack supposedly has her own truck…
 

@Keith Mowz  
I’d guess that they probably do have trucks, since self propelled vehicles have either been shown or mentioned a few times now. Like you said, though, they still can’t really beat ships for this kind of scale.

Anyone else getting a Warcraft-y feeling from these ships?
 
Those kind of exaggerated proportions the whole series has had since the original game and are present in bulk both in Warcraft 2’s ships and their WoW versions.

@thps48  
Presumably they’re just shipped up the coast from where they’re raised. Its much easier to move large amounts of cargo in bulk via ship compared to rail (smaller cargo cap and vulnerable to the tracks being sabotaged; war time and all) or carts. (since they don’t have truck technology.)

@thps48  
The processing centers they need to work the sheep’s wool are probably in that area.  
The sheep have probably been in farms and grazing fields and now they need to transported to where they can be processed.

Why are they emigrating a species that already bleeding lives in Equestria? XD

@Evowizard25  
Thank you. I knew I was being neglectful about that.

@FSin  
No, we’ve seen a few ships, such as in Rarity Takes Manehattan.

Ah yes, the not-slaves must do their part too.

Maybe I’m being forgetful but are these the first actual ships we’ve seen in the series?