The only stretch where you might see a bear is in the Delaware Water Gap National Recreation Area and Worthington State Forest, in New Jersey of all places. While I have never had the pleasure of seeing on during the numerous times I have ridden up there, sightings are relatively frequent. As noted, they usually try to avoid human interaction.
South of Port Jervis, NY camp at the campground at Worthington State Forest. $25/night for non-residents of NJ. At least one of the group sites has a bear locker. Use it if you stay there. The place is nice and along the river. Flush toilets and showers.
There are not any services along the route from Port Jervis to Delaware Water Gap, PA except for water and bathrooms at Old Millbrook Village. When you get to Worthington, you can set up camp and make the relatively easy ride to DWG for supplies and then return to camp. There is no grocery store there, but there is a diner and a convenience store at a gas station. There are also a couple of other places to eat.
South of DWG there is not much in the way of camping except in/around Portland, PA, which is not that far from DWG. The next logical place to camp is Dogwood Haven in Upper Black Eddy, PA, slightly off route from Milford, NJ. The place is a bit dated but the owner is a very nice guy, and it's pretty quiet and surrounded by wood. At least through last year he was offering a discounted rate of $15 for cyclists. That's cheap when you consider that Driftstone on the Delaware, a bit south of Portland, charges some $35. Haven't been there this year so I don't know what he's charging.
I am extremely familiar with this part of the route down to Philly. Send me a private message if you would like more information that you will ever need.