Cherokee includes a web admin interface for configuring the server. To get that running you need to start it up on your server and then use SSH tunnelling to view in a local browser. So on your server run the following to start the Cherokee Admin deamon:
cherokee-admin -b &
Then on your local machine, setup the SSH tunnel as follows:
-L 9090:localhost:9090 mysite.com -N
Now, navigate to http://localhost:9090 and log in using the username and password shown in the output on your server console. You should be greeted with the Cherokee Admin home screen!