[10] Because of its age and constrained location in Boston's dense Fenway–Kenmore neighborhood, the park has many quirky features, including "The Triangle", Pesky's Pole, and the Green Monster in left field.

[2] Some of the changes include:[25] On May 15, 1999, then-Red Sox CEO John Harrington announced plans for a new Fenway Park to be built near the existing structure.

[40] The proposal was highly controversial; it projected that the park had less than 15 years of usable life, would require hundreds of millions of dollars of public investment, and was later revealed to be part of a scheme by current ownership to increase the marketable value of the team as they were ready to sell.

[42] A significant renovation of Fenway Park stretched over a 10-year period beginning around 2002 headed by Janet Marie Smith, then Vice President of Planning and Development for the Sox.

[61] Fenway Park is one of the two remaining jewel box ballparks still in use in Major League Baseball, the other being Wrigley Field; both have a significant number of obstructed view seats, due to pillars supporting the upper deck.

It was built there primarily for the benefit of Ted Williams, to enable him and other left-handed batters to hit more home runs, since it was 23 feet (7.0 m) closer than the bleacher wall.

Aerial shots show it to be noticeably shorter[80] than the (actual) 302 foot line in right field, and Pesky has been quoted as estimating it to be "around 295 feet".

Mark Bellhorn hit what proved to be the game-winning home run off of Julián Tavárez in game 1 of the 2004 World Series off that pole's screen.

Facing Reds right-hander Pat Darcy in the 12th inning with the score tied at 6, Fisk hit a long fly ball down the left field line.

The wall also served as a spectator-friendly seating area during the dead ball era when overflow crowds, in front of the later Green Monster, would sit on the incline behind ropes.

The base of the left field wall is several feet below the grade level of Lansdowne Street, accounting for the occasional rat that might spook the scoreboard operators.

[90] Outside Gate 5 is The Teammates statue, by Antonio Tobias Mendez, which depicts Red Sox players Bobby Doerr, Dom DiMaggio, Ted Williams, and Johnny Pesky.

"[98] The Yawkey Way Report also came with baseball cards, ponchos and tote bags, which caused Rutstein to file his own complaints with Boston city code enforcement.

[101] Since at least 1997 Neil Diamond's "Sweet Caroline" has been played at Fenway Park[102] during Red Sox games, in the middle of the eighth inning since 2002.

[104] Beginning in 2006, the Red Sox have hosted the "Futures at Fenway" event, where two of their minor-league affiliates play a regular-season doubleheader as the "home" teams.

The MVP of the 1977 contest was future major league slugger Steve Balboni, who clobbered two home runs over the Green Monster that day.

The 2009 game starred East division MVP and future Boston Red Sox Chris Sale of Florida Gulf Coast University.

Although Eddie Shevlin and Paul Doyle fought in the feature bout, Daniel J. Saunders of the Boston Daily Globe described heavyweights Battling McCreery and John Lester Johnson as "the only boxers who caused any excitement".

[117] On September 2, 1930, Babe Hunt defeated Ernie Schaaf in what The Boston Daily Globe described as a "dull bout" and a "big disappointment".

The undercard included future light heavyweight champion George Nichols, who defeated Harry Allen of Brockton, Massachusetts in ten rounds.

[147] [citation needed] On July 9, 1929, World Heavyweight Champion Gus Sonnenberg defeated Ed "Strangler" Lewis in front of a crowd of 25,000 at Fenway Park.

[160] On June 29, 1937, around 7,000 spectators saw Steve Casey defeat Ed Don George in a card that also featured Danno O'Mahony, Tor Johnson, and William "Wee Willie" Davis.

[164][165] Fenway Park has hosted ice hockey games on five separate occasions, beginning in 2010 when the third annual NHL Winter Classic was held at the stadium on New Year's Day.

[166] The Boston Bruins beat the Philadelphia Flyers 2–1 in sudden-death overtime, securing the first home-team victory in the relatively short history of the annual series.

Frozen Fenway is a semi-annual series of collegiate and amateur games featuring ice hockey teams from local and regional high schools, colleges, and universities.

[167] Fenway Park became the first stadium to host two Winter Classic games in January 2023, as the Boston Bruins once again secured a 2–1 victory, this time defeating the Pittsburgh Penguins.

[175] Since 2003, there has been at least one concert every year at Fenway by such artists as Bruce Springsteen and the E Street Band, Jimmy Buffett, Billy Joel, Shakira, Journey, Def Leppard, The Rolling Stones, Neil Diamond, The Police, Jason Aldean, Mötley Crüe, Dave Matthews Band, Tom Petty & The Heartbreakers, Aerosmith, Phish, Roger Waters, Paul McCartney, James Taylor (2015–2017 consecutively: 2015 & 2017 with Bonnie Raitt, 2016 with Jackson Browne), Pearl Jam, Foo Fighters, Dead & Company and New Kids On The Block 2011 (with Backstreet Boys), 2017 and 2021.

[179] On July 31 and August 1, 2023, Pink performed at the stadium as part of her Summer Carnival tour, and broke the record for biggest two-day attendance.

[185][186] Fenway used a series of guest announcers to finish the 2012 season[note 2] before hiring Henry Mahegan, Bob Lobel, and Dick Flavin for 2013.

Dan Shaughnessy pointed out that the numbers, when read as a date (9/4/18), marked the eve of the first game of the 1918 World Series, the last championship that the Red Sox won before 2004.