kottke.org posts about fenwaypark
The under-construction facade of the new Apple Apr 29 2008
Susan Orlean attempts to answer the question Jan 19 2006
Design and Fenway Park Sep 15 2005
One of the pre-conference events was a talk at Fenway Park followed by a tour of the ballpark. Janet Marie Smith, VP of planning and development for the Sox, kicked things off with how the team (especially the new management) works really hard to preserve the essential character of Fenway while at the same time trying to upgrade the park (and keep it from getting torn down). She talked about the advertisements added to the Green Monster, which was actually not a purely commercial move but a throwback to a time when the Monster was actually covered with ads.
Lots of talk and awareness of experience design...the Red Sox folks in particular kept referring to the "experience" of the park. One of the speakers (can't recall who, might have been Jim Dow) talked about how other ballparks are becoming places where only people who can afford $100 tickets can go to the games and what that does to the team's fan base. With Fenway, they're trying to maintain a variety of ticket prices to keep the diversity level high...greater diversity makes for a better crowd and a better fan base and is quite appropriate for Boston (and New England in general), which has always been an area with vibrant blue collar and blue blood classes.
Janet also referred to the "accidental" design of the park. Like many other urban ballparks built in the late 19th/early 20th centuries, the placement of the streets constrained the design of Fenway and made it rather an odd shape....these days larger plots are selected where those types of restraints are removed. And over time, the game has changed, the needs of the fans have changed, and the fire codes have changed and the park has changed with the times. In the dead ball era, the walls of the stadium weren't for hitting home runs over; their sole function was to keep people on the street for catching the game for free, so the Fenway outfield ran over 500 feet in right field -- practically all the way to the street -- where there's now 30 rows of seats. Jim Holt observed that American butts have gotten bigger so bigger seats are called for. Fire codes helped that change along as well...wooden seats, bleachers, and overcrowding are no longer a large part of the Fenway experience (save for the wooden seats under the canopy).
The design talk continued on the tour of the park. Our guide detailed how ballparks are built around specific ballplayers. Yankee Stadium was the house that Ruth built but it was also seemingly (but not literally) built for him with a short trip for his home run balls to the right field wall. Boston added a bullpen to make the right field shorter for Ted Williams. Barry Bonds does very well at PacBell/SBC/WhateverItsCalledTheseDays Park. And more than that, the design of Fenway also dictated for a long time the type of team that they could field, which had some bearing on how they did generally. Players who played well in Fenway (i.e. could hit fly balls off of the Monster in left) often didn't do so well in other parks and the team's away record suffered accordingly.