Had the oppportunity to play Fenway for the first time in 15 years with Brad Miller and Geoffrey Childs and I have to say it's a course that's way too undervalued when course ratings are mentioned.
The facility has been artfully restored throught the efforts of Gil Hanse and the inherent design qualities that made Tillinghast a top flight architect are there for all to see. The interplay between the bunkering and putting surfaces is simply first rate.
In regards to the "walk in the park" test Fenway is indeed no different than many courses you find in the older suburbs because of the amount of development that has encircled them over the years. The property is a sheer delight and walking it is pleasure. Without doubt, Fenway has better land than neighboring Winged Foot although both courses at WF are more demanding through and through.
The only weak aspect of the course, in my mind, is the 1st hole. However, keep in mind the revered Cypress Point has a weak link as well with the 18th hole there. I also don't believe the "tree issue" is that big a deal with Fenway. Yes, there can be some tweaking here and there (i.e. 5th / left side, 8th / left side (?), left side at the 9th, pulling out the small ones behind the 12th green, the over hang at #17 and some work on #18). If people really dig their heels in with the "tree issue" other courses such as Ridgewood (NJ) will take even more of a drop when evaluated.
Fenway competes, in my mind, at such a level that a case can be easily made that the depth of holes there are better than three other NY metro area courses currently ranked in the top 100 by GD with two of them also being Tillinghast layouts. They include the following:
Quaker Ridge
Somerset Hills
Maidstone
Fenway has enough diversity in all of its holes to thoroughly test all types of players. As far as Jeff Lewis' comment / re: 6th hole, I say leave the hole at 245 yards for those who have the b*lls to play it from there. GC had no problem with the hole yesterday after smashing a first rate driver to 20 feet and calmly stroking it home for a sweet two.
Unfortunately, they day we played was one day removed from a major rainstrom that hit the area in Saturday. Play Fenway under firm and fast conditions and you will be tested in order to properly control all of your shots -- especially on the greens!
I've played 92 of the current GD 100 Greatest listing and can't for the like of me believe Fenway isn't among that listing -- in fact, I'd say the course has serious credentials for even top 50 consideration.
I hope to return when conditions are a tad drier because the design ingredients will only be more magnified.
P.S. If for some reason the course could ever add on about 150-200 yards the demands would only be even more intense. As I said previously, I'd love to see Bethpage Black have the green contours you find at Fenway -- then you'd have the ultimate test for the world's best instead of the flat cookie-cutter types you find at too many holes at the Black.