The following are our findings and comments for various sites that we use, have used, or have looked at and decided not to use. They are (very roughly) in order of best to worst.

Mt. Equinox FN33kd This is a great site, with a few things to watch out for. During the June and September contests, WB1GQR operates from the top. We have found that if we try to operate from the top, the interference between both of us is unacceptable. Therefore, we operate from the last pullover before the top which is well blocked to the top and helps a lot. It is quite open in all directions except north give or take 30 degrees. Also, if you do operate from the top, there is a hotel north of the parking lot, so that if you want to operate to the north or northwest, you have to be on the far side of the parking lot and if you want to operate to the northeast, you have to be on the near side of the parking lot. Another thing to look out for is that there is an antique race car rally on the mountain in June and it usually is the same weekend as the June contest. When the rally is on, the road is closed from about 10:00 in the morning to about 4:30 in the afternoon. The road up is a toll road, I think the toll was $9.00 for the two of us. The road is paved the entire way, but steep and you do have to watch for trees (our travel height is nearly 12 feet). Unfortunately, the hotel is now closed so there is no place for lodging, food, or restrooms at the top. Although it is a tourist attraction, we have never been bothered with too many curious people. The views are spectacular (see photo on our home page)
Sam's Point FN21tq For us this has been a good site, but the road is closed to the public and hard to get permission to use. Also the road is VERY poorly maintained (read totally unmaintained), and I am very glad I have 17 inch wheels and 4 wheel drive. If you have a setup that allows you to hike up the hill about a mile from the parking lot, it is great. Now that it is owned by a conversancy group, we do get a whole new line of questions (like how dangerous is the radiation from all these transmitters on the top)
Hogback Mt. FN32ou This site was just recently added to our list and is working out quite well. It is one of the few sites near our route that has a good shot into EMA, RI, eastern CT, southern NH and ME. (The other good one is Equinox). There is a tourist facility (read gift shop) with restrooms and limited food (hot dogs, ice cream etc.). It is quite a busy place with a lot of curious people around, but a good operating spot.
Point Lookout Inn FN22wi We picked this site to have a good place to stay overnight on Saturdays. It is quite high (nearly 2000 feet) and has a great shot to the east. We have worked W2SZ on all bands up to 10G, and have worked K1WHS and KT1J as high as 3456. There is a public pullover just down the hill east of here that is also quite good
Galway FN23xb The area around route 29 and route 147 in Galway is not at all bad. It is reasonably high at almost 1000 feet and has worked well for us. The high point on 29 west of 147 would be good if you can find a spot to be off the road well enough to be out of traffic. There are a few parking lots around, but I have not gone after permission. We just park on the side of one of the side roads.
West Charlton FN22xx We picked the area around West Charlton on route 147 mostly because it is reasonably high (around 800 feet), fairly open, and not out of our way. It is not as good a site as Point Lookout, but has worked reasonably well without too much driving
Pleasant Ridge FN31ep We chose this site just this year since it is very close to home. It is reasonably high at about 1200 feet and fairly open with not many trees. It is a residential area, but we were not bothered by the residents. Its not an ideal site, but worked reasonably well.
The following are sites that we have eliminated from our choices for the reasons given
Mount Greylock FN32jp Although this can be a great site, we can not use it because of the low overhead clearance of trees on the way up. I have used it in the 10G contest, and it is indeed a great site. Also W2SZ is at the top for all three summer contests, and there is a lot of RF in the air. When I tried a VHF contest, I operated from a ways down the road. The road is not a toll road, but there is a modest parking fee for the parking lot at the top. If you want to be on the top of the peak, it is not in the parking lot. W2SZ operates from the very top, but I understand there is a very expensive special use permit required to do so.
Overlook mountain FN22wc In our (so far unsucessful) search for a really excellent FN22 site, we did take a look at overlook. I have not been all the way to the top in many (over 30) years so I don't know the condition of the road or trees. Way back then, the visibility from the fire tower was indeed impressive and it is over 3000 feet, so it would have promise. However we did go to the gate and indeed the road is chained and locked. We have not pursued it further.
North Lake FN22xe Another attempt at a great FN22 site was unsucessful. If you pay the entry fee (modest) and go to the last parking lot, there would be a great shot to New England except for a lot of tall trees. There is a power line that comes up the hill, but from the parking lot the opening is only about 10 degrees wide. By moving around the parking lot, you can cover 30 degrees or so, but not a great deal more. I did manage to work both AF1T and W1MKY on Block Island (FN41ee) from here on 10G (about 180 miles) . All the roads off the sides of the access road have no open space either.
Mohawk Mountain FN31jt Although this is a much better site than the one we are now using for FN31, it is a long way out of the way for us about an hour each way) so we no longer go there (remember every hour of driving time is an hour less of good operating time)