This Fat Ass is a Graduate Level run, meaning you will be on some of CT's most technical and gnarly trails: first the Regicides (West Rock's "Blue" trail) and then The Quinnipiac Trail (another of CT's famed Blue trails). Hence, the Blue 2 Blue Challenge (h/t Alex McDaniel for the idea). There's probably a good 6,000 feet of climbing and the majority of it is extremely technical.
This is an out-and-back starting at West Rock Playground (alternately named "Amrhyn Field") in New Haven, climbing up the Westville Feeder Trail and depositing you onto Regicides for about 6+ miles of some of the gnarliest, rockiest trail you can imagine. Then, the fun really starts as you climb up High Rock to the intersection of the Q Trail. You will follow blue blazes down to the first aid station at Brooks Rd, then climb up to Mad Mare Ridge before a nice little descent to a one mile road section on Downs Road, crossing Gaylord Mountain Road, then continuing on asphalt before going back on dirt right before the Y Camp. You'll summit Mt. Sanford at mile 12, then cross Route 42 near Holiday Hill before another climb up to the backside of Roaring Brook Park (home to CT's tallest waterfall). Then you'll continue on to the turnaround aid station where the dirt hits Cornwall Ave in Cheshire.