I’ve been to Lynchburg and Danville from the song Wreck of the Old 97. Lynchburg was nicer IIRC.
Also been to Rockingham County and Route 33 from the Old Crow Medicine Show song Dixie Avenue.
Johnny Horton sang “North To Alaska”, which mentioned crossing the Yukon River and a place “a little southeast of Nome”. Done the first and been to the second.
There are several songs that mention Timbuktu. Done that.
Toto mentions “Kilimanjaro rising like Olympus above the Serengeti”. Climbed partway up Kilimanjaro and also spent a week in the Serengeti. I’ve also heard the “wild dogs crying in the night”, although it was daytime.
The Duprees sang about “see the pyramids along the Nile” in “You Belong To Me”. I’ve been there many times.
Like most Chicagoans, I’ve also driven on Lake Shore Drive. I’ve also danced on State Street, that great street (but not with my wife, not having one). I’ve driven the Ventura Highway in California, and visited Strawberry Fields in Central Park (not sure that one counts). I’ve been to Trader Vic’s, but alas did not have a Pina Coloda, nor was my hair anywhere near perfect.
According to Google Maps I’m 18+ hours flying time from Tulsa Oklahoma [which seems a bit optimistic to me] so, allowing a bit of time to get to the airport, Customs and baggage I’m pretty much exactly where Gene Pitney was when he dumped his wife.
Every town in Getting your kicks on Rt 66. Not obscure.
Stockbridge, MA Alice’s Restaurant
Lodi, NY heh heh, never actually stuck there but lived next town over in Ovid. Not the same Lodi as song but certainly obscure.
Marrakesh Express by CSNY. Morocco, wonderful intense smells. And some death warmed over ones as well. Not obscure, just out of the way.
For obscure - Bristol, PA “famous” in the song “Bristol Stomp” by The Dovells
I’ve seen the sun set red over Copano bay, but wasn’t on the deck of a saltwater lady at the time.
Paducah, Ky has been name-checked in several country songs, but most notably in the second verse of “Hooray for Hollywood.”
“I’ve Been Everywhere” would be a good metric. Johnny Cash’s version is well known, though I prefer Hank Snow. The towns listed on the Cash version are as follows:
Reno
Chicago
Fargo
Minnesota
Buffalo
Toronto
Winslow
Sarasota
Whichta
Tulsa
Ottowa
Oklahoma
Tampa
Panama
Mattua
LaPaloma
Bangor
Baltimore
Salvador
Amarillo
Tocapillo
Pocotello
Amperdllo
Boston
Charleston
Dayton
Louisiana
Washington
Houston
Kingston
Texarkana
Monterey
Fairaday
Santa Fe
Tollaperson
Glen Rock
Black Rock
Little Rock
Oskaloussa
Tennessee
Tinnesay
Chickapee
Spirit Lake
Grand Lake
Devil’s Lake
Crater Lake
Louisville
Nashville
Knoxville
Omerback
Shereville
Jacksonville
Waterville
Costa Rock
Richfield
Springfield
Bakersfield
Shreveport
Hakensack
Cadallic
Fond do Lac
Davenport
Idaho
Jellico
Argentina
Diamondtina
Pasadena
Catalina
Pittsburgh
Parkersburg
Gravelburg
Colorado
Ellisburg
Rexburg
Vicksburg
Eldorado
Larimore
Adimore
Habastock
Chadanocka
Shasta
Nebraska
Alaska
Opalacka
Baraboo
Waterloo
Kalamazoo
Kansas City
Souix City
Cedar City
Dodge City
I’m at around 65%
Another Hank Snow song with a town is “Duquesne, Pennsylvania”, but that only gets you one. 
You did notice that the OP specified obscure places, right?
I’ve been to the California and New Jersey Lodis, but the Ohio one is a new one on me.
Also been to Marrakesh, but not by train. My favorite place in Morocco, except for the seaside oyster beds.
Since I grew up on the Lower East Side of Manhattan, I’ve been on all of the streets mentioned in Billy Joel’s “Big Man on Mulberry Street” - the titular Mulberry, Houston, Canal, Hester, and (last but not least) Grand, the street on which I actually lived.
(Where I lived is actually a good dozen blocks or so away from the parts that Joel is really referring to, in Little Italy, which has now been mostly swallowed up by an expanding Chinatown. But I’ve certainly been to the actual parts that he’s referring to.)
I’ve been to both the Cumberland Gap and to Johnson City, Tennessee. It is most definitely not west to go from the former to the later. I was even born in Johnson City.
Been to other not so obscure places mentioned in Wagon Wheel as well.
Me and Bobby McGee: “Somewhere up near Salinas, lord, I let him slip away…”
Been there [Salinas, CA – seat of Monterey County, Steinbeck Country…] many times.
I too have been on Broadway and every other place listed in the song - including the closed Taco Bell (which no longer exists) and, of course, Dick’s.
I’ve been to La Isla Bonita (Ambergris Caye).
I have been to MANY places in many songs…
I followed the Grateful Dead for a long time and have definitely been to ShakeDown Street
The only place in a song I have ever sought out to find, and explore is Paradise KY…I have been to every place mentioned in the song, sans the original Paradise. It is now a power plant; coal fired!
Wikipedia says he changed the location in the lyrics to be a better fit for the song to be a response to the song Hot Rod Race, but the actual race between the writer (in his Lincoln) and his friend in the Cadillac was indeed up the Spiral Highway.
Here’s my obscure location from an equally (or more?) obscure song. St. Francis Dam Disaster by Frank Black (aka Black Francis of the Pixies) tells the story of the 1928 dam collapse and flood that killed 400 or more people from the Santa Clarita valley in Californa all the way down to Ventura where the Santa Clara river meets the Pacific. The dam failure ruined what was left of William Mulholland’s career and was mentioned as part of the water wars in the movie Chinatown.
I was just there a few weeks ago, standing on the remains of the “tombstone”, the center section of the dam that was still standing after the collapse. After a kid tried to climb the tombstone section, then fell and died, they blew it up and only a rubble pile remains. Plus scars on the hillside where the dam met the terrain and where the flood scoured the rock away.
Song with video made from annotated photography from the period.
Same here…often at 2AM…back in the day.
Oddly enough I can’t even find an online version of “I Hang My Hat in Ballard” by Stan Boreson
Just like the song, I have never been to Fairbanks Alaska. I have been to Lincoln (the other place mentioned in the song), but not golfing. And I have not been everywhere else, but I am working on that (it is taking longer than I thought).
Did you ever make it to Lahaina?
But don’t you want to get stuck in the Lodi in Wisconsin? I mean, they have… ummm … a duck.
I’ve been to the Bowery, Peaches Corner, and The Magic Attic. All are referenced in Alabama’s Dancing (Shagging on the Boulevard). I’ve also been on Ocean Blvd. All are in Myrtle Beach, SC. I can’t remember any other places in the song, but, due to a misspent youth, I’ve probably been to them, too.