Here's the dilly... I estimate my usual ride from Clifton to Glen Ridge and back is about 35-40 miles with some decent hills and one killer hill (Eagle Rock Reservation) which I call "Terminator 2: Judgement Day". My friends and I name all the hills after Arnold movies ha ha. I did this ride just under 3 hrs last weekend. The only crap parts are cutting through some parks where peeps get in the way and some traffic lights.
You're definitely welcome to come out here but if you wanna do an assessment of each other's riding skilz b4 that, I'm def down to meet in CP this weekend. I haven't made it there this year yet.
Whatever you want to do is cool.
Steve