By Rich Schott
This adventure kicked off bright and early, or should I say, dark and early! We were up at 3:30 AM to catch our flight and landed in Nashville around 7:30 AM. We hit the shops and dove headfirst into the quintessential Nashville experience looking for a new pair of cowboy boots. We stumbled upon Doc Holidays and then discovered the most amazing Sunday Brunch Bluegrass session at Acme Feed & Seed. Seriously, bluegrass and brunch? A match made in heaven.

A quick pit stop at Lainey Wilson's place, Bell Bottoms Up, to say hi to friends who had just arrived in Nashville. Then, it was time for a much-needed nap to recharge for the whirlwind days ahead. Dinner and live music at Assembly Food Hall was next on the agenda. The concept is fantastic, with a ton of different food options and a lively atmosphere.
Later, we met up with our friends Mike, Grace, Jimmy, and Charley from New York to dive into the heart of Nashville's honky-tonk scene. We hit Rippy’s, Alan Jackson’s AJ’s Good Time Bar, and ended the night at Garth Brooks' Friends in Low Places. The highlight of the evening was discovering Tera Lynne Fister, an incredible band that had us hooked from the first note.
Day two was all about continuing the boot search. I'm a big fan of Ariat; their boots are seriously comfortable, which I did find the perfect pair. Lunch was at Sun Diner, where we indulged in hot chicken and waffles. Spicy and sweet – the perfect Nashville combo!

More friends arrived in the afternoon – Jerry & Vivian from Michigan and Judy from Florida – and we all headed back to Broadway for another round of honky-tonk hopping. We started at Kid Rock’s Big Honky Tonk, where we caught another fantastic band. Then, it was on to John Rich’s Redneck Riviera. This place is super patriotic, and we even got in a few games of cornhole on the rooftop bar.
Dinner was at Blake Shelton’s Ole Red, where Wild Bill and the Bruisers put on an absolutely awesome and entertaining show. We also made a stop at Morgan Wallen’s This Bar for more great music and, of course, had to pay homage to the legendary Tootsie’s Orchid Lounge.
To cap off the night, we ventured to Bon Jovi’s bar – JBJ’s – to rock out to an 80s hair band. It was amazing to experience such a wide variety of music all in one day. We ended up clocking over 24,000 steps in our cowboy boots!
The third day took a more touristy turn. We met up with friends for a bus tour around Nashville. We hopped off for lunch at the Farmers Market, which was bursting with delicious options. Back on the bus, we made our next stop at Losers Bar and Riley Green’s Duck Blind. We heard whispers that Riley Green and other musicians might be making a surprise appearance the next day.
Abandoning the rest of the bus tour, we decided to head back to the hotel and get ready for the main event: the Grand Ole Opry! This was a first for Jen and me, and it was truly an unforgettable experience. The lineup was incredible: Lainey Wilson, Lauren Alaina, Russell Dickerson, Dan + Shay, Carter Faith, Gabby Barrett, and Noeline Hofmann.
After the show, Ubers were impossible to find, so we ended up walking a mile to Scoreboards for dinner and more live music. This place had a great vibe, and it was the perfect spot to wind down the day. We added another 14,000 steps to our cowboy boot count – we definitely get around!
Our final day, started a bit later. We grabbed lunch in Printers Alley and indulged in some bourbon, moonshine and wine tastings at Big Machine Distillery and Nashville Barrel Company. We had tickets at the Ryman Auditorium to see Bill Murray and his Blood Brothers. However, after hearing about the possible pop-up appearance, we decided to take our chances and check it out.

We headed over to Losers Bar, and it was definitely more than just a pop-up appearance. It was a full-blown, free concert in the parking lot for their 21st Anniversary! The lineup was insane: not only Riley Green, but also John Pardi, David Bryan (keyboardist for Bon Jovi), Drake White, Love & Theft, Myles Morgan, and DJ Travisty.
It was the perfect way to wrap up our Nashville adventure – an awesome evening of music and camaraderie. Nashville, you were amazing! The combination of incredible music, delicious food, friendly people, and of course, cowboy boots, made this trip one for the books. We can't wait to come back!
Wild Bill and the Bruisers @ Ole Red
Lainey Wilson @ the Opry
Dan + Shay @ the Opry
Riley Green @ Losers 21st Anniversary
You can find more videos on our Good Life Destinations YouTube Channel