“Why did the chicken cross the road?”/“To get to the other side” is a classic riddle from the 19th century. A yo-yo version is:   
   
Q: Why did the yo-yo cross the road?
A: It was walking the dog.
     
“Walk the dog” is a yo-yo technique. “why did the yoyo cross the road? Because it was walking the dog” was posted on Twitter by Liam Fussell on January 23, 2012.
   
     
Wikipedia: Yo-yo 
A yo-yo (also spelled yoyo) is a toy consisting of an axle connected to two disks, and a string looped around the axle, similar to a spool. It is an ancient toy with proof of existence since 500 BCE.
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Techniques
Sleeping
The sleeper is one of the most common yo-yo throws and is the basis for nearly all yo-yo throws other than looping. Keeping a yo-yo spinning while remaining at the end of its uncoiled string is known as sleeping. While the yo-yo is in the “sleeping” state at the end of the string, one can then execute tricks like “walk the dog”, “around the world”, or the more complex “rock the baby”.
     
Twitter
Liam Fussell
@LiamFussell
Replying to @Turnballz
@ScottJkz @jon_fuey @katcarruthers why did the yoyo cross the road?
Because it was walking the dog
2:39 PM · Jan 23, 2012·Twitter for iPhone
     
Twitter
Yosune
@Y0YOo
Why did the yoyo cross the road?
Because it was walking the dog! Ha
2:42 PM · Mar 21, 2012·Plume for Android
 
Twitter
Air Traffic
@AirTrafficToys
Why did the yoyo cross the road?.................  Because it was walking the dog.
9:30 PM · Aug 8, 2012·Hootsuite
     
Google Books
I Even Funnier:
A Middle School Story
By James Patterson and Chris Grabenstein
New York, NY: Jimmy Patterson Books
2013
Pg. ?:
“Why did the yo-yo cross the road? Because it was walking the dog!”
 
Twitter
Kenneth Resuello
@HadouKennnn
Why did the Yoyo cross the road? Cause he was walking the dog! HAHAHA! Get it?!
8:41 PM · Jan 26, 2013·Twitter Web Client
   
Twitter
Jason
@RutterJason
Replying to @102megan
@102megan
Why did the yoyo cross the road?
To Walk the Dog 😊 #YoYoComedy
6:27 AM · Aug 14, 2014·Twitter Web Client
   
Twitter
A.R.T. NYC
@artnycgirl
Why did the #yoyo cross the road? Because it was walking the dog *LOL* | Happy National… https://instagram.com/p/3mFmb3xtwL/
12:53 PM · Jun 6, 2015·Instagram
 
Twitter
Kim Harman
@trixieedgewood
Why did the yo-yo cross the road? Because it was walking the dog.
11:43 AM · Mar 27, 2017·Twitter Web App
 
Twitter
Bird in Hand
@birdinhandchico
Why did the #yoyo cross the road? Because it was walking the dog. | Photo: igot.cherrica | #BirdinHand #ChicoCA #YOYOMuseum
2:35 PM · May 8, 2017·Hootsuite
 
Twitter
Chapman Toys
@ToysChapman
Why did the yoyo cross the road? Because it was walking the dog.
10:36 AM · Jun 9, 2020·Twitter for Android
   
Twitter
Kappa Toys
@KappaToys
Why did the yoyo cross the road? Because it was walking the dog!
The Fireball by Yomega is a yo-yo first released in 1989 - travel back in time and perfect your around the world!
#Yomega #KappaToys #WalktheDog #DadJokes #YoYo #toystagram
2:17 PM · Jun 25, 2021·Hootsuite Inc.
 
Reddit—Jokes
Posted by u/Automatic_Wrap_2166 December 23, 2021
Why did the yoyo cross the road?
It was walking the dog