The dates after the song and artist are the year that each one became a state.
1. Delaware - Brigid Kaelin - December 7, 1787
2. Pennsylvania Pal - Red River Dave - December 12, 1787
3. I'm From New Jersey - John Gorka - December 18, 1787
4. Going To Georgia - Ralph Stanley - January 2, 1788 - Listen Below
5. Connecticut Snow - David Stephens - January 9, 1788
6. Massachusetts - Aaron Lewis - February 6, 1788
7. Maryland, My Maryland - Tennessee Ernie Ford - April 28, 1788
8. South Carolina Low Country - Josh Turner - May 23, 1788
9. New Hampshire Naturally - The Shaw Brothers - June 21, 1788
10. 'Mid The Green Fields of Virginia - Jim & Jesse - June 25, 1788
11. New York Town - Flatt & Scruggs - July 26, 1788
12. Under North Carolina Skies - Cecil Campbell & His Tennessee Ramblers - November 21, 1789
13. Rhode Island - The Bluerunners - May 29, 1790
14. Moonlight In Vermont - Willie Nelson - March 4, 1791
15. Blue Moon of Kentucky - Bill Monroe - June 1, 1792
16. Tennessee Waltz - Patsy Cline - June 1, 1796
17. Beautiful Ohio - Hank Snow - March 1, 1803
18. Beautiful Louisiana - The Shelton Brothers - April 30, 1812
19. Indiana (Back Home Again In Indiana) - Stuart Hamblen - December 11, 1816
20. Mississippi Gal - Ernest Tubb - December 10, 1817
21. Illinois - Brett Eldredge - December 3, 1818
22. Alabama - The Louvin Brothers - December 14, 1819
23. Tombstone Every Mile - Dick Curless - March 15, 1820
24. Missouri - Merle Travis - August 10, 1821
25. My Arkansas Sweetheart - Jimmie Davis - June 15, 1836
26. Saginaw, Michigan - Bobby Bare - January 26, 1837
27. Come And Live In Florida - Undergrass Boys - March 3, 1845
28. Yellow Rose of Texas - Wilf Carter - December 29, 1845
29. Iowa Rose - Eddie Dean - December 28, 1846
30. Milwaukee, Here I Come - Porter Wagoner & Dolly Parton - May 29, 1848
31. Blue Yodel No. 4 California Blues - Jimmie Rodgers - September 9, 1850
32. Missing Minnesota - Rich O'Toole - May 11, 1858
33. Portland Oregon - Loretta Lynn - February 14, 1859
34. North To Kansas - R.W. Hampton - January 29, 1861
35. Wheeling Back To Wheeling West Virginia - Kidd Baker - June 20, 1863
36. When It's Night Time In Nevada - The Cass County Boys - October 31, 1864
37. My Nebraska Homestead - Red Steagall - March 1, 1867
38. Colorado - The Vic Willis Trio - August 1, 1876
39. Dakota Wind - The Flying J Wranglers - November 2, 1889
40. Casey Tibbs (South Dakota Cowboy) - Rusty Richards - November 2, 1889
41. Back On Montana Plains - Patsy Montana - November 8, 1889
42. It's Raining In Seattle - Wynn Stewart - November 11, 1889
43. Idaho-Ho - Deuce Spriggins w/ Ken Curtis - July 3, 1890
44. In The Hills of Old Wyoming - Jimmy Wakely - July 10, 1890
45. The Red Hills of Utah - Marty Robbins - January 4, 1896
46. Oklahoma Hills - Jack Guthrie - November 16, 1907
47. Land of Enchantment, New Mexico - The Sons of The San Joaquin - January 6, 1912
48. Arizona Sunset - The Reinsmen - February 14, 1912
49. North To Alaska - Johnny Horton - January 3, 1959
50. Blue Hawaii - Hank Locklin - August 21, 1959
Bonus Songs
51. Canada I-O - Stu Phillips
52. South of The Border (Down Mexico Way) - Gene Autry
