How to master the Tennessee Whiskey Trail

Uncharted Traveling
Find adventure and fun on the Tennessee Whiskey TrailPhoto by Thomas Thompson/Unsplash

I first learned about the Tennessee Whiskey Trail on a trip home from Chattanooga to Memphis, when my boyfriend (now husband) and I made the decision to take a short detour and check out the George Dickel distillery in Cascade Hollow. He was already a whiskey lover and was pretty pumped to add to his extensive liquor collection. But me, I was a different story. What exactly was whiskey neat, and was it good or bad if it burned on the way down?

So wanting to be the cool girlfriend, I figured I could choke down a few whiskey samples and fake my way through. After a VERY cool tour, we sat down at the tasting bar and I said a little prayer that I wouldn’t actually choke when I drank the first sample. Everyone else looked so calm and collected, I was obviously the only first-timer there. I swirled, and smelled, and sipped, let the spirit roll down my tongue so I could taste the front AND the back. And just like that, I was hooked on Tennessee Whiskey.

Over the next 12 months, we made it our mission to visit all 27 distilleries on the Tennessee Whiskey Trail (and a few that weren't). We knew we would have a blast taking weekend road trips and tasting whiskey. What we didn't know was how many really cool places we would get to visit along the way. Throw in a free t-shirt, and I was sold!

Read on to find out how you too can master the Tennessee Whiskey Trail in eight easy road trips!

Middle Tennessee: Where it all began

The distilleries in middle Tennessee are quite literally out in the middle of nowhere. It makes sense if you think about it though. The two oldest distilleries in Tennessee are in this area, and when they first began they needed two things. A fresh source of limestone spring water, and a location far away from the eyes of the law. That’s how George Dickel ended up in Cascade Hollow, and Jack Daniel set up shop next to a cave outside the small town of Lynchburg.

This part of Tennessee is charming and beautiful, with rolling hills as far as the eye can see. A weekend here will steal your heart, and may just turn you into a whiskey snob! There are five distilleries in this area that can easily be visited in one weekend. You just need to be strategic about the direction you travel and where you stay.

Three of them are closed on Sundays, so you’ll need to travel the route from West to East. As far as where to stay? We found an amazing Airbnb farm stay near Fayetteville for Friday night, and a different Airbnb on the square in Lynchburg for Saturday night. But you can just as easily stay in one or the other for both nights.

Here is your distillery tour route. Start out Saturday morning with Tenn-South Distillery in Lynnville. Yes, I’m telling you to start your first distillery tour by 10:00 am. Be brave. Whiskey tasting ain’t for sissies.
Tenn South Distillery, LynnvilleJenny Feleciano/Uncharted Traveling

You’ll drive through Fayetteville on your way to Southern Pride Distillery. There's a square at the corner of Main Avenue and Market Street with a couple of greasy spoons, local boutique shops, and a surprising number of antique stores. Grab some lunch and walk off the whiskey and moonshine you’ve tasted so far. These small, family owned distilleries are NOT stingy with their samples.

Plan to be at Prichard’s Distillery by 2:00, because they close at 3:00. Then plan on an early dinner in Lynchburg. Their historic square has multiple dinner options, and quite a few antique, memorabilia, and candy shops that are fun to browse in. Guys, now is a good time to reward your girl for her whiskey tasting bravery with a stop at the Lynchburg Winery tasting room.

Sunday, you’ll want to have reservations for tours at the Jack Daniel's and George Dickel distilleries in order to allow yourself travel time between the two. They’ll each take a couple of hours, but it will be time well spent! The history and stories will draw you in, and the whiskey will make you a believer.

There isn’t much between these two, so you’ll want to eat lunch in Lynchburg before leaving, or stop in Tullahoma on your way home. There's a new kid in town as well. Nearest Green Distillery, in nearby Shelbyville, is brand new and has a VERY cool story I'll let you discover on your own.
George Dickel Distillery, Cascade HollowJenny Feleciano/Uncharted Traveling

This takes care of your first whiskey tasting weekend! Feeling inspired to try some whiskey adventures for yourself? Check out my other weekend guides on how to master the Tennessee Whiskey Trail. Happy whiskey tasting, and please drink responsibly!

Chasing the Tennessee Whiskey Trail in Memphis

How to spend a weekend whiskey tasting in Nashville

Taking the Tennessee Whiskey Trail to Chattanooga

A whiskey tasting weekend in Knoxville

Tennessee Whiskey Trail: Moonshine in the Mountains

The end of the line for the Tennessee Whiskey Trail

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Local city guide for Memphis Tennessee, reporting on current events, entertainment, and all the best places to eat and drink. And a few cocktail recipes here and there!

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