27 Best Songs About Massachusetts

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“Sweet Baby James” by James Taylor

Song Year: 1970

“Sweet Baby James” comes from James Taylor’s second album. This song wasn’t as popular as the hit “Fire and Rain,” but it’s a memorable tune with Taylor’s signature guitar style slowed down to resemble a waltz.

The song is about his nephew James. The lyrics describe the family’s life in Boston and evoke the cold New England winters.

“Alice’s Restaurant” by Arlo Guthrie

Song Year: 1967

“Alice’s Restaurant” is a blues song that tells a memorable story inspired by real events. The story begins at a restaurant in Stockbridge, MA, where Arlo Guthrie is enjoying a Thanksgiving dinner and ends up with the singer becoming ineligible for the military draft.

It’s a memorable song against the Vietnam War despite its humorous tone.

“M.T.A.” by the Kingston Trio

Song Year: 1959

“M.T.A.” is a satirical song about the Massachusetts Transportation Authority increasing the subway fare in Boston. The song tells the tragic story of a man who never came home because he didn’t have enough change to get off the train.

It’s a fun novelty song, but it’s memorable because of the serious tone of the introduction that tricks listeners into thinking the lyrics will be about a real-life tragedy.

“Dirty Water” by the Standells

“Dirty Water” by the Standells

Song Year: 1966

“Dirty Water” refers to the River Charles that flows through Boston. This classic ‘60s song describes life in Boston, including crime and factory work.

However, the tone remains positive thanks to the upbeat tempo of the song and the singer’s repeated love for the city of Boston.

“Please Come to Boston” by Dave Loggins

Song Year: 1974

“Please Come to Boston” is a beautiful pop and folk song that earned Dave Loggins a Grammy Award. The ballad is about the singer asking a girl to follow him around the country. He asks her to come to Boston and stay there with him for a while.

The girl answers that the singer should come back home to Tennessee and settle down.

“Miss Massachusetts” by Tori Amos

Song Year: 2007

“Miss Massachusetts” is a song that Tori Amos improvised during a concert in Boston. It’s a humorous song about an encounter between Miss Massachusetts and Donald Trump.

The song is a fun tune that showcases Tori Amos’ talent when it comes to writing original lyrics.

“Maryland, Massachusetts” by Nelly

Song Year: 2013

“Maryland, Massachusetts” is an upbeat RnB song from Nelly. The rapper repeats the name of two states in the hook, which is a possible reference to drugs since the states’ abbreviations come together to form the acronym MDMA.

“Massachusetts” by the Andrew Sisters

Song year: 1942

“Massachusetts” is a classic song featuring the Andrew Sisters’ signature harmony. The song is about missing Massachusetts and wanting to come home to New England.

The lyrics also make fun of the New England accents by highlighting how the pronunciation of some words is different.

“Roulette” by the Red Hot Chili Peppers

Song Year: 2022

This recent track from the Red Hot Chili Peppers is a bittersweet song that looks back on a relationship. The lyrics have multiple references to music from the ‘70s and ‘80s and suggest this love story took place back in college.

The singer compares his ex-girlfriend to a ‘Massachusetts threat,’ which might be a catchy rhyme or a reference to them attending college in Massachusetts.

“Small Town” by Nappy Roots

Song Year: 2008

“Small Town” is a rap song that celebrates life in a small town and talks about wanting to get away from a busy city. The chorus refers to Massachusetts and West Virginia, two places the group associates with the countryside.

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