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Steve Rubin 4Steve Rubin 4 

Why won't trailhead open up my playground??!! I've done all the setup, but it keeps sending me in circles to create anew ID or password. Really frustrating.

Rahul KumarRahul Kumar (Salesforce Developers) 
Hi Steve,

Then I would suggest you log out of all the accounts and log in again and also clear your browser cookies and history.
 OR
Another solution would try it in a different browser.
 
Please feel free to contact me if you need any further information.Mark, it as best answer if it resolved the issue.

BestRegards
RahulKumar
NagendraNagendra (Salesforce Developers) 
Hi Steve,

What is a Trailhead Playground?
A Trailhead Playground (TP) is your own personal Salesforce org that you'll use to tackle hands-on challenges. A Trailhead Playground is actually a Developer Edition (DE) that has been customized with Trailhead-specific bells and whistles. What else is cool about TPs?
  • You can store a TP on your Trailhead profile so you don't need to log in each time you tackle a hands-on challenge.
  • If you need a new TP, you can create up to 10 org's at any time.
  • Easily switch between org's via the hands-on org drop-down menu.
  • We've installed a managed package in your TP to customize your org with Trailhead-specific goodness, such as custom data/metadata and a welcome tab. We'll update these resources over time and push changes to your org automatically.
    As soon as you select "Create a Trailhead Playground" (TP) our trailboats will start creating a new playground for you. You can only spin up one TP at a time. Check on the org's progress by opening the hands-on org drop-down menu. If the org is still being created, you'll see a spinning arrow icon next to the org label. Once the org is created you will see it in the hands-on org's list in the dropdown and it should be set to default. Launch your new org by clicking the “Launch your hands-on org” button.

Still, if the problem persists may I suggest you to please raise a case with trailhead support team for better assistance.

You can reach trailhead support below. Please mark this as solved if the information helps.

Regards,
Nagendra.