If you want to hills, I recommend Green Pond Road between Rt 80 and Rt 23. That stretch is about 10 miles long. I used to work on Green Pond Road near Rt. 80, and would bike to work from Stockholm, NJ, so I'm familiar with biking on there.
Probably the biggest hills you'll find in Rockaway, and relatively safe to bike on. The only problem is there are some sections where the shoulder almost non-existent, and there's a high curb and a guardrail, all at the same time. It's a good test of balance and control to stay as far right as possible without hitting your pedal on the curb or guardrail. Fortunately, this isn't much of the length. No traffic lights, and very few intersections, so you can ride w/o stopping for 10 miles.
This would be an out-and-back. You might be able to put a loop on end in West Milford (Route 23 has w i d e shoulders there and is very bike-friendly), but I can't think of any good ways to loop back on the Rt. 80 side. You could do Green Pond -> Rt 23 N -> Oak Ridge Road/Berkshire Valley Road -> Something else, but iding on 15 south of Berkshire Valley Road isn't very bike friendly, so things get complicated after that. Even if you continued on Berkshire Valley Road to Rt 46 or Rt. 10, I still can't think of an easy way back to Green Pond Road that's very enjoyable by bike. There could be something - I don't know all the local roads that well - just the highways and county roads.
I am going to be in the Craigmeur area to watch the cross, race and then was hoping to find a good loop right around there. I am looking for some good climbing because I have all the flats I need where I live.
good loop from there? are you on a true road bike or a cross? if you're on a cross (or just wanna ride), you could head DOWN greenpond road to meridan, hook a left, follow it to the end, hook another left, follow it to splitrock road, hook yet another left then go up, up, up. when you hit the dirt road keep going. after you cross the one lane bridge, you'll be on dirt for awhile yet then it'll hit pavement again. at the next stop sign make a right. follow that back to greenpond road and make a right. that should do.
here's a good 40 mile loop with a nice mix of scenery, a few decent hills, and a reasonable proximity to civilization. you'll pass a few delis, etc along the way if you run out of fluids. do it clockwise to finish with a climb, counterclockwise to have tougher climbs enroute and finish heading downhill. if craigmeur won't let you park there after the races, there is a church just up the road that should, or you can park by the ball fields near 23.
I'd suggest taking Rt. 80 to the Rockaway/Hibernia exit (head north at the bottom of the ramp) and parking in the lot of the former Damons resturant. Turn left heading North towards the Cragmiuer ski area for 9.9 miles. It will be a 10 mile ride to the race are4a, you can hang out, watch the races and have a bombing fast ride back to your car. the ride North will be pretty hilly and challenging though a great ride .
and here is a significantly less hilly route, 35 miles long, with more than it's share of scenery. it is a generally very hilly area. for new jersey anyway. it does however, have a long valley with an overall very gentle grade, which in this route would encompass the entire middle of the ride. you would start on a really short uphill, followed by a generally downhill direction, then slightly rolling to flat, then climb to the finish.