Creating a custom navigational menu

Hi,

I have a blog about running/hiking/racing/travel. (www.hikeinhongkong.com).

There are posts from 2003 and what I want to do is to build a custom menu based on the post title.

For example: these are some post titles:

Race: Wilson Trail: Oct 2012, running Wilson on an ankle sprain
Race: Wilson Trail: Oct 2011, quitting Wilson trail halfway
Race: Trailwalker: November 2011, Finishing in 16 hrs 15 minutes
Race: Trailwalker: November 2010, leisurely pace 18 hours

What I want is a menu on the side bar that navigates like this:

RACE -> Wilson Trail –> Oct 2012, running Wilson on an ankle sprain
-> Wilson Trail –> Oct 2011, quitting Wilson trail halfway
-> Trailwalker –> November 2011, Finishing in 16 hrs 15 minute
-> Trailwalker –> November 2010, leisurely pace 18 hours

So, it’s a hover menu on the Sidebar that pulls up links to Posts based on the title.

I am a coder (Perl mainly) but does anyone have any relatively easy way of doing this?

Thanks!!

Vince