Best Songs About Richmond

One of the jewels of the southern US, the state of Virginia has a storied history and is steeped in tradition. The capital city of Richmond plays an enormous role in the state’s past and present, and songwriters have captured various aspects of it in song for many years. Here are some great songs about Richmond.

1. “James River Blues” by Old Crow Medicine Show

Song Year: 2006

Old Crow Medicine Show’s music often sounds like the tunes of yesteryear, and “James River Blues” does, too.

The narrator travels down the James River to Richmond. He’s a boatman, and technology and advancements in transportation are rendering him obsolete. With freight shipping moving from boats to trains, he’s got little to live for anymore, and he’s adrift in life, both figuratively and literally.

2. “Rainy Day in Richmond” by Bobby Bare

Song Year: 1969

“Rainy Day in Richmond” was vintage Bobby Bare. He was as much a storyteller as a country singer, and the song tells the tale of a man stopping off in Richmond, Virginia, on a rainy day. He spends his time there thinking back on his life and relationships.

From Bare’s album, Bobby Bare Sings Lullabys, Legends, and Lies, “Rainy Day in Richmond” has Bare’s vocals, a simple guitar, and a lilting groove underlying it all. It’s a song that relies on the writing rather than fancy production values.

3. “My Cabin in Caroline” by Flatt and Scruggs

Song Year: 1952

“My Cabin in Caroline” isn’t so much about Richmond as it is about leaving Richmond. Lester Flatt and Earl Scruggs were bluegrass superstars, so it makes sense that many songs they recorded— including this one— became standards of the genre.

The song tells about a man who sets out to live in a cabin in Caroline County but to do that, he has to leave his home in Richmond and build that cabin himself.

4. “Dear John” by Aimee Mann

Song Year: 1993

After her time with one-hit wonder ‘Til Tuesday, Aimee Mann went on to a storied career as a songwriter. “Dear John,” from her solo effort, Whatever.

The ballad recounts a relationship that began years ago at a fair in Richmond and perhaps ended when the narrator’s partner went off to war. A “Dear John” letter ends a relationship, so Mann using the phrase as the song’s title foreshadows how things will end.

Mann has a recognizable sound in the song, and even though the electric guitar is featured a little more prominently than in much of her other music, it’s still definitely an Aimee Mann song.

5. “Night Train” by James Brown

Song Year: 1962

The Hardest Working Man in Show Business used “Night Train” to show off just how hard he was working.

The song began its life in the 1940s with Duke Ellington, but when James Brown added his signature funk sound to it, he also added a shout-out to many cities in the US, listing places he had been to perform his terrific live shows. One of those stops was Richmond.

He probably didn’t do too much of his touring aboard any train, but “Night Train” is, like so much of Brown’s music, so much fun to listen to.

6. “Old Richmond Prison” by Ralph Stanley and the Clinch Mountain Boys

“Old Richmond Prison” by Ralph Stanley and the Clinch Mountain Boys

Song Year: 1990

Ralph Stanley was a bluegrass music legend whose work got a boost in popularity when it got featured in the George Clooney film O Brother, Where Art Thou?

Before the film’s success, though, Stanley and his band were making great music that the bluegrass community already knew was of the highest quality.

“Old Richmond Prison,” tells the story of a young man who kills a law enforcement officer and gets sentenced to prison. As he does his time, he thinks back to life before his crime and wishes he could return home and leave Richmond Prison behind.

7. “Modern Day Bonnie and Clyde” by Travis Tritt

Song Year: 2002

A good, old-fashioned ballad in the sense that it’s a song telling a story, “Modern Day Bonnie and Clyde” tells of ill-fated lovers who commit a robbery in Tennessee. They flee to Richmond, and while counting the money in a hotel room, the police descend upon them.

The reference to Bonnie and Clyde intimates that the pair goes out in a bloody blaze of glory, but the lyrics don’t specify what happens after the police arrive.

A twist to the tale is that in this song, the woman is the criminal, roping the man into her schemes after meeting him at a truck stop. Travis Tritt brings a cool factor to the story, too.

8. “Virginia Reel Around the Fountain” by The Halo Benders

Song Year: 1994

The Halo Benders was a collaborative project featuring Doug Martsch from Built to Spill and Calvin Johnson of Beat Happening. The pair recorded God Don’t Make No Junk and included “Virginia Reel Around the Fountain” on the album.

While the song doesn’t mention Richmond specifically, the Virginia Reel in the title is a dance from days gone by, hence the lyrical reference to doing the do-si-do. It’s about as indie rock as music gets, complete with lo-fi music production values. It’s an unusual piece of music but inexplicably very cool.

9. “Richmond is a Hard Road to Travel” by Chris Thile

Song Year: 2013

Chris Thile made a name for himself as the virtuosic mandolin player in Nickel Creek. He struck out on his own for some solo work and dabbled in radio (taking over A Prarie Home Companion when original host Garrison Keillor retired) and remains a legendary player.

He contributed “Richmond is a Hard Road to Travel” to a 2013 project called Divided and United: The Songs of the Civil War, which included performances of songs from the era from artists like Loretta Lynn, Ricky Skaggs, Old Crow Medicine Show, Vince Gill, and a host of others.

The song, written in the 19th century, mentions some Civil War battles and generally describes the hardships faced by the Confederate soldiers as the tide of the war turned against them. 

10. “Oregon Hill” by Cowboy Junkies

Song Year: 1992

The Oregon Hill neighborhood in Richmond gets the treatment here from Cowboy Junkies as part of their album Black-Eyed Man. It’s got a slow-ish, bluesy burn to it as it tells of some of the people and goings-on in the area.

The lyrics get some directions wrong— they mention the state prison being north of the area, though, in real life, it was to the east— but the feel of the song captures the neighborhood’s spirit, which can be a little rough, but to the narrator, it’s home.

11. “Sweet Virginia Breeze” by The Robbin Thompson Band

Song Year: 1978

Sounding every bit the 1970s song that it is, “Sweet Virginia Breeze” sings the praises of Old Dominion. The title track from The Robbin Thompson Band’s 1978 album, the song celebrates the beauty and spirit of Virginia.

While it doesn’t specifically reference Richmond, since that’s the capital city, one would assume the city is included in all the nice things Thompson sings about the state.

It was named the official state popular song in 2015.

Top Songs About Richmond, Final Thoughts

Richmond, Virginia is a lovely city in a beautiful state. It’s no wonder songwriters have used it as an inspiration. Some of these songs are about Virginia in general, but the vital city of Richmond rears its head in all these songs, even if it’s not mentioned by name.

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