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Description

This is the earliest appearance I’ve found of horseshoes as the quintessential pony lawn game. Also the first appearance of hot air balloons as a major source of aerial adventure hijinx, beating Tales by 6 or 7 years.
 

 
My Little Pony and the Country Fair (1984)
 
Remarks from the source posts –
 
Comments [part 1]: I love the arm randomly thrusting a candied apple at Blossom from off-page. It looks like it’s going to end up in her mane.
Also, Medley is a special pony! You can tell because she is super strong. Not because she’s green and talks.
Comments [part 2]: The description of Medley taking flight is lovely.
 

safe2232494 artist:julio herrera1 artist:sharon lisman1 applejack (g1)798 blossom254 medley352 peachy110 pony1662628 g122071 official12931 adrift2 book45130 carnival213 church334 everypony laughs ending15 fair66 fairground ride7 ferris wheel285 flying57389 high res411288 high striker24 horses doing horse things1550 horseshoes3106 horseshoes (game)5 hot air balloon1261 janet1 jerry5 my little pony at the country fair2 nickering9 picture book12 random house2 rescue386 steeple7 story980 writer:melinda luke1

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when she felt her wings unfold
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Goodbye Ponk Pie Hat
@Background Pony Number 17  
And I thought it was just the stock pony art. But there’s all sorts of weird stuff going on in this one
 
  • Blossom hurling those horseshoes directly at Medley. Aren’t you glad—CLINK! that her aim—CLINK! is so perfect–CLINK!?  
  • The ponies on the ground are huge in the aerial shots.  
  • AVERT YOUR EYES FROM THE BEING IN THE BELFRY, CHILDREN  
  • That ferris wheel doesn’t seem to have any safety harnesses at all, let alone ones what work for two children and a small horse.
Background Pony Number 17
My Little Pony - 1992 Edition

Okay, getting a serious eldritch horror vibe from this comic.
 
The ponies are looking straight at us.  
In every pose.  
In every panel.  
They’re not even paying attention to where they’re going or what they’re doing.  
Their vision is fixed on the 4th wall. At us.