Best Bluegrass Songs (you'll wish you heard earlier)

65 Best Bluegrass Songs (you’ll wish you heard earlier)

Bluegrass music would never have happened if it wasn’t for the various races that settled in America. During the 1600s many English, Irish and Scottish people moved to the “new world”, and took with them the basic musical styles that become the roots of bluegrass. Many of these settlers moved to places like Virginia, West Virginia, North and South Carolina, Tennessee and Kentucky.

They started to write songs about their daily life living in a new land, many were living on remote farmsteads or mountainsides. Their songs and music reflected the way they lived and how they worked etc. Many called this music Country, Mountain or Hillbilly music and as it developed influences from Gospel and the Blues mixed in with it.

Table of Contents

A Brief History Of Early Bluegrass

By the early 1900s most homesteads had at least one fiddle player, guitarist or banjo picker, in many cases they had all three. Around this time a fellow from Rosine Kentucky called Bill Monroe and his brother Charlie left the family’s farm and moved to Chicago to find work. After some time they formed a band called the Monroe Brothers.

When they split up Bill ended up forming another band called Bill Monroe and the Bluegrass Boys. Bluegrass was born, they went on to play at the Grand Ole Opry in 1939. In 1945 Earl Scruggs joined the band, he was a banjo player with a particular picking style that’s still used and known as Scruggs Style.

65 Best Bluegrass Songs 

Let’s get started with the best Bluegrass songs, in no particular order. We’ll start with Bill Monroe & The Bluegrass Boys.

Uncle Pen – Bill Monroe & The Blue Grass Boys

Uncle Pen was actually about Bill Monroe’s real Uncle Pen who was christened James Pendleton Vandiver born in 1869 in Butler County, Kentucky.

Foggy Mountain Breakdown – Earl Scruggs & Lester Flatt

This is the original 1949 version that was used on the soundtrack of the film Bonnie And Clyde. After the film, the instrumental was re-recorded but at a slower speed. This version is how it was supposed to sound.

Blue Moon Of Kentucky – Bill Monroe & The Bluegrass Boys

Written by Bill Monroe in 1946 this track went on to be a hit for Elvis Presley in 1954.

I’ll Fly Away – Alison Krauss & Gillian Welch

This 1929 hymn by Albert E. Brumley has been covered literally 100s of times, this version featured on the soundtrack of the 2000 film O Brother, Where Art Thou?

Wagon Wheel – Old Crow Medicine Show

Originally written and recorded by Bob Dylan, this bluegrass version by the Old Crow Medicine Show was released in 2004.

 Freight Train – Jim & Jesse

The McReynolds brothers from Virginia were Bluegrass performers from 1945 until 2002.

Rocky Road Blues – Bill Monroe & The Bluegrass Boys

Written and first recorded in 1946 by Bill Monroe this track epitomises the spirit of Bluegrass.

Goin’ Back To The Pickin’ Shack – The Hillbilly Gypsies

This original track by the Hillbilly Gypsies from West Virginia proves that Bluegrass is alive and well even now.

Sittin On Top Of The World – Molly Tuttle and Billy Strings

Live from the Grey Fox Bluegrass Festival in Oak Hill NY. These two great guitarists make this old Bluegrass standard their own.

Black Mountain Rag – Doc Watson

Black Mountain Rag was composed during the 1930s by fiddle player Leslie Keith. Doc Watson gives one of the best renditions here.

Bluegrass Express – Rhonda Vincent & The Rage

Written and first released in 1964 by Bobby Osborne and covered many times over the years. This cover expresses the way it should sound.

Kentucky Waltz – Bill Monroe

Written by Bill Monroe in 1946 this was Bill’s most successful song on the C & W charts.

Sally Goodin – Byron Berline

First released in 1923 by the Texas fiddler Eck Robertson, this tune is a classic.

Sparkling Brown Eyes – Joe Val & The New England Bluegrass Boys

Written and released in 1938 by Bill Cox and Cliff Hobbs and covered numerous times like this one from 1982.

Orange Blossom Special – Southern Raised Bluegrass

It’s time to board the Orange Blossom Special with this version by Southern Raised Bluegrass with a hint of classical thrown in for free.

Blue Side Of the Mountain – Steeldrivers

The Steeldrivers when Chris Stapleton was with them. Written by Chris Stapleton and Mike Henderson. 

The Legend Of The Rebel Soldier – The Country Gentlemen

Written by Charlie Moore and recorded in 1971,  this track is about a Confederate soldier missing his home from his prison cell.  It seems to be based on the Irish folk song Kevin Barry.

Salt Creek – Tony Rice

First recorded, written and released in 1931 by the Kessinger Brothers, Salt Creek was made famous by Bill Monroe.

Mule Skinner Blues – Bill Monroe

Written by Jimmie Rodgers and George Vaughan and first recorded in 1930, this track has been covered many times. Originally titled Blue Yodel#8.

Mountain Dew – Grandpa Jones 

Written in 1928 this Bluegrass classic started life as The Good Old Mountain Dew but the title got shortened over the years.

Sunny Side of the Mountain – Jimmy Martin

This track has had many covers over the years. This version from the self-described King of Bluegrass Jimmy Martin.

Ground Speed – Earl Scruggs

Written and recorded by Earl Scruggs in 1961, showcases the skill of Earl on that banjo.

Jerusalem Ridge – Mark O’Connor

Co-written by Kenny Baker and Bill Monroe in 1970, Jerusalem Ridge has been covered many times. Mark O’Connor is a fiddle master and brings that tune alive.

Rocky Top – Osborne Brothers

First released in 1967 by the Osborne Brothers was voted as one of Tennessee’s official state songs. 

I Am A Man Of Constant Sorrow – Soggy Bottom Boys

Another Bluegrass standard, covered by many. This version by the Soggy Bottom Boys was featured on the soundtrack of the film O Brother Where Art Thou?

Molly and Tenbrooks – Brooklyn Bluegrass Collective

Another Bill Monroe classic Bluegrass track. Played for us this time by the Brooklyn Bluegrass Collective.

Paradise – The Seldom Scene

The Seldom Scene treats us to this John Prine song about the devastation caused by strip mining.

Fox On the Run – North Country

First recorded by the English band Manfred Mann in 1968, where it reached number 5 in the singles charts. Introduced to bluegrass by Bill Emerson where it has become a favourite among bluegrass musicians and listeners too.

Sweet Dixie – Bill Emerson and Sweet Dixie

Bill Emerson of The Country Gentlemen, performing here with his band Sweet Dixie, a track entitled Sweet Dixie.

In Hell I’ll Be In Good Company – The Dead South

The Dead South are a Canadian Bluegrass band from Saskatchewan. From the album Good Company and with a great catchy tune we bet you’ll be whistling this one long after it’s finished.

Old Number 7 – The Devil Makes Three

This track about the Jack Daniel’s distillery refers to the brand name assigned to the distillery for government registration.

Crying Holy unto the Lord – Flatt and Scruggs

This song illustrates just how integrated the musical genres are that make up Bluegrass.

The Wreck of the Old 97 – Lester Flatt

Lester Flatt relates the tale of the American rail disaster when the Southern Railway mail train was travelling too fast to remain on schedule and derailed. With just 18 crew members on board the crash accounted for 11 fatalities and 7 injuries, another survivor was a crate full of canaries that escaped and flew to safety.

You’ll Never Leave Harlan Alive – Patty Loveless

Patty Loveless’ version of the Darrell Scott song You’ll Never Leave Harlan Alive. The opening lyrics say

“In the deep dark hills of eastern Kentucky

That’s the place where I trace my bloodline

And it’s there I read on a hillside gravestone

“You’ll never leave Harlan alive””

Ghosts Of Mississippi  – The SteelDrivers

Another track by the Steeldrivers featuring Chris Stapleton.

Better Way – Watchhouse (fka Mandolin Orange)

Just a beautiful song, played live at Fresh Grass in 2021.

Ghost Riders In The Sky – Southern Raised

This old classic given a new twist by Southern Raised, an award winning band.

All I Want Is You – The Nashville Bluegrass Band

From their 1987 album, entitled The Nashville Bluegrass Band. 

Blue Virginia Blue – Larry Sparks

From the album Silver Reflections released in 1994.

This Heart of Mine – Billy Strings

Billy Strings performs This Heart Of Mine in 2017 for the Creekside Sessions.

Worried Man Blues – Wade Mainer

This Bluegrass standard, still popular to this day. Performed here by Wade Mainer.

Midnight Rider – Greensky Bluegrass

What an amazing transformation of this old pop classic. Greensky Bluegrass have done a great job here.

Walk In The Irish Rain – Bluegrass Hoppers

You can certainly hear the Irish influence on this track.

Girl’s Breakdown – The First Ladies of Bluegrass

The First Ladies of Bluegrass is an all female group who made their debut, along with special guests Phoebe Hunt and Sally Van Meter, in the summer of 2018 at the 46th annual Rocky Grass Festival in Lyons, Colorado and yes that is Molly Tuttle playing guitar.

Going Up The Country – Del McCoury & Friends

Another pop classic being given the Bluegrass treatment, this time the Canned Heat song from 1968.

Fraulein – The Tennessee Bluegrass Band

This fine quintet performs the Jimmy Martin classic Fraulein.

Daniel Prayed – Ricky Skaggs and Patty Loveless

This gospel/Bluegrass song performed by two great Bluegrass stars, Ricky Skaggs and Patty Loveless.

 Pretty Polly – Ralph Stanley and Patty Loveless

Another Bluegrass standard performed by two accomplished Bluegrass stars.

Catfish John – Nitty Gritty Dirt Band

Written by Bob McDill and Allen Reynolds and first released on Bob McDill’s album Short Stories in 1972 Performed here by Alison Krauss, Jerry Douglas, Randy Scruggs and The Nitty Gritty Dirt Band.

Blue Side Of The Mountain – The SteelDrivers

Another classic Steeldrivers song featuring Chris Stapleton.

C’est Le Moment  – Caleb Klauder Country Band

Performed live at Pickathon 2013.

Reuben’s Train – Foghorn Stringband

This Bluegrass standard is performed here by Foghorn Stringband.

Turkey in the Straw – Sam Bush & Sierra Hull

Another classic Bluegrass tune, played here by Sam Bush & Sierra Hull.

Drink Up and Go Home – Bill Monroe & The Bluegrass Boys 

This classic Bluegrass song performed in 1959 by Bill Monroe and the Bluegrass Boys.

Little Maggie – Billy Strings and Molly Tuttle

This Bluegrass standard is performed by 2 of the next generation of Bluegrass stars, Billy Strings and Molly Tuttle.

Wayfaring Stranger – Hayde Bluegrass Orchestra

Another Bluegrass standard performed this time by the Hayde Bluegrass Orchestra live at John Dee in 2018.

Nine Pound Hammer – Lonesome River Band

This classic Bluegrass song first performed in 1927 by Al Hopkins and his Buckle Busters. 

Big Spike Hammer – Russell Moore & IIIrd Tyme Out

Big Spike Hammer originally by Doc Watson is another Bluegrass classic performed here by Russell Moore & IIIrd Tyme Out.

Girl At the Crossroads Bar – Thile and Daves

This Larry Sparks song has been covered numerous times. This time by Thile & Daves

Tennessee 1949 – Larry Sparks

Released in 1987 by Larry Sparks and still a great track today.

Cotton Eye Joe -The Hillbilly Gypsies

This old standard Performed at Rockville Hometown Holidays 2013 by the Hillbilly Gypsies.

 Will The Circle Be Unbroken? – Nitty Gritty Dirt Band

Another classic Bluegrass/Gospel song performed here by the Nitty Gritty Dirt Band.

Nashville Cats – Del McCoury Band

A Bluegrass version of the classic 1966 song by the Lovin Spoonful.

Tennessee – Jimmy Martin & the Sunny Mountain Boys

Jimmy Martin was born in Sneedville, Tennessee, so this track was personal to him.

When My Blue Moon Turns To Gold Again – Bill Monroe

The Father of Bluegrass performing this classic Bluegrass track that was also sung by Elvis Presley in 1957 on the Ed Sullivan Show and it was on his album Elvis from 1956.

What About You?

That’s our 65 Best Bluegrass songs, what did you think of them? Have we missed any you would have included? How about some of the younger artists we chose? Do you think they merit inclusion?

What songs would you have in your top 5 Bluegrass songs? And sung by who? Let us know in the comments.

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