Do I need to go to the webpage between upgrades, and can this be bypassed?

The documentation for the upgrade process specifically states:

Running the website - First request

Open the upgraded website in a browser. When handling the first request, the system performs certain tasks required to finalize the upgrade. This includes the import of new objects. Processing of the first request may take longer than usual.

Important: The first request must be performed using the upgraded project files. The process will not be successful if you only upgrade the database and connect it to a new Kentico project.

The short answer is YES you need to run the site after each major AND minor upgrade. See below:

Upgrade v7 -> v8.0, run site
Upgrade v8.0 -> v8.1, run site
Upgrade v8.1 -> v8.2, run site
Upgrade v8.2 -> v9.0, run site
Upgrade v9.0 -> v10.0, run site
Upgrade v10.0 -> v11.0, run site

With an upgrade from v7 to v11, you're going to be performing 6 upgrades. In my 10 years experience with Kentico, you're better off starting with a new install of Kentico 11 and migrating your custom code and content to that instance. The upgrade will be too painful and cost you more time and money in the long run.

Hi Jason,

There is no shortcut for bypass the step's it's should be performed in incremental manner.

Recommended: In your site if no custom development made then you can go with an upgrade process else better to start with new installation as suggested by Brenden.