I believe it connects with the high peak trail, but with the weather I'd stick to the Tissington Its a while since I was down there [15 Years] but I sem to remember it climbs a bit.
Second Derek's suggestion of the V-Graphics gudiebook - the Tissington Trail is dullsville btw, even for southerners
Have a look at the Manifold Valley or South Buxton routes from the book, both a stone's throw from Ashbourne. Buy it as an inspiration investment and come back for more later in the year.