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541 Wiley Parker Road
Jackson TN 38305


A Bar Crawl Through Downtown Jackson


A Bar Crawl Through Downtown Jackson

Gabe Hart


A few years ago I was talking to a friend of mine who lives in Denver about her plans for the evening. She told me she was going on a bicycle pub crawl. I had no idea what she was talking about. She explained that she and a group of her friends would rent bicycles and ride around downtown Denver and visit the local pubs and bars in the area. The idea was to have one drink at each location and then move on to the next place via bicycle. This sounded like a great idea for several reasons, but two jumped to the front of the list:

  1. There was no concern about driving a car under the influence. That’s very important when it comes to consuming alcohol.
  2. Changing venues after every drink keeps you a little more sober a little longer than sitting in one place and having multiple drinks. It also lets you experience a variety of atmospheres in one night.

I was sold. However, there was one small issue. In order to have a bar crawl, I needed multiple establishments within walking distance of one another. The only places to go downtown at the time were the Downtown Tavern and Charlie Bulldog’s.
About three years ago, I was in Texas for my daughter’s first day of school. I dropped her off at her mom’s and had a whole Sunday night to myself before meeting her at school the next morning. I was sitting in downtown McKinney, Texas, and to my right I could see The Pub at McKinney, to my left I could see Cadillac Pizza Pub, and behind me was The Celt (and Irish bar). It all clicked. I was going to finally have my own bar crawl . . . by myself. It was a little anti-climactic because I was alone, but it still gave me a taste of what a great idea it could be if I were with a group of people. Then, I got a little frustrated because I remembered Jackson had only two venues I could visit while walking.
Fast forward three years, and that’s not the case! Finally, I was able to have my first bar crawl with my friend, Josh Garcia, in Jackson, Tennessee! Lucky for you, I made notes and tried special drinks at each place. And Josh was kind enough to take some awesome pictures that capture the atmosphere of each place. So, without further ado, here is your first official guide to going on a bar crawl in Jackson, Tennessee.

Grubb's Grocery

4 Jackson Walk Plaza

Our first stop was Grubb’s Grocery. Yes, that’s right—Grubb’s Grocery store. I bet you didn’t know you could get farm-fresh groceries and local and regional beer fresh from the tap at the same place. Caitlin Dhillon guided us through the drink selection process. She recommended a Bell’s Oberon, which is the only beer they serve that’s brewed outside of Tennessee. Once Josh and I paid for our beers, we made our way out to the patio facing North Highland. Even though the temperature was pushing a little close to the record high set in Hell a few years ago, it was still easy to imagine sitting on the patio after work on a Thursday afternoon in late September. The atmosphere at Grubb’s was a great way to start our crawl. And, what’s more, the price of a pint on Thursday’s is only $2! The Oberon had a hint of citrus that I could compare to Blue Moon but with a much better quality and flavor. It  was a perfect beer to start with because it wasn’t heavy at all, nor did it have an incredibly high alcohol content. After we finished our beers and water (side note: consume water with every stop while bar crawling), we made our way west about thirty steps to Rock’n Dough Pizza.

Rock'N Dough Pizza & Brew Co.

16 Jackson Walk Plaza

Rock’n Dough holds a special place in my heart because it was the first restaurant downtown that really seemed to signal that change was taking place. We made our way to the bar. Neatly hung on the wall was a fashionable chalkboard with the beers listed along with each beer’s gravity and alcohol content. Since I went light at Grubb’s, I decided I needed to get a little serious about my drinking. I selected a beer called “2 Hops Shakur” and then turned my bandana around and tied it in the front—just to make sure I was ready. The “2 Hops” had 6% alcohol content and the beer was much fuller than the one I started with at Grubb’s. That was when I realized I needed to steal some of Josh’s cheddar bacon fries (imagine Outback’s Aussie cheese fries but better) to have some food to balance out the drinks I had consumed (side note number two: you need to eat at one of your stops, at least). While I was sneaking fries from Josh’s bowl, one of the managers at Rock’n Dough, Lewis Silvers, came to speak with us. He informed us that the bar at Rock’n Dough was about get a little more diverse. In three weeks, Rock’n Dough will receive their liquor license and, along with that, unveil a new drink menu with specialty cocktails. A few drinks stood out to me from the menu: 

  1. Moscow Mule: I’ve had these before at the Downtown Tavern, and they’re a favorite of mine. The drink consists of Tito’s Vodka, ginger beer, and fresh-squeezed lime juice. I highly recommend it.
  2. Love Me Tender: I’ve never had this, but I like whiskey, so it jumped off the page. Its ingredients are Buffalo Trace whiskey, house-made blackberry-strawberry puree, and fresh-squeezed lemon juice. 
  3. Old Fashioned: This was the drink that turned me on to drinking whiskey. As soon as I heard Don Draper order one on Mad Men, I needed to do the same. Unfortunately, my voice doesn’t have the same gravitas as Mr. Draper’s, and when I order one no woman asks me to light her cigarette, but at least he and I can drink the same drink. The Old Fashioned has Buffalo Trace whiskey and Angostura orange bitters.

Lewis also told us that Rock’n Dough will once again brew their own beer in the restaurant. They also offer trivia on Wednesday nights and will soon serve pizza by the slice (cheese, pepperoni, and special of the day) on Monday nights. Monday nights will also be $3.50 pint nights. After our first two stops, Josh and I were incredibly impressed with each venue and excited that we still had three places to hit.

Fleet Street Pub

216 North Shannon Street

Up the hill and to the left of Rock’n Dough is Fleet Street Pub. It’s housed in the same building where Charlie Bulldog’s was. Fleet Street specializes in English food and beer. It is a “pub” in every sense of the word. We were greeted by Wendy Graham who was tending bar. Since I’m a bit of a novice in English beer, I had her recommend one for me. She started me off with an ESB, which is an English-Style Pale Ale. It was a perfect follow-up to the beer I had at Rock’n Dough. The ESB was smooth, and the bar was an excellent place for us to catch our breath for bit and have some conversation about the places we had been so far.

Annie Tennyson is the general manager for Fleet Street, and she spoke with us about what makes Fleet Street a great fit downtown. She explained that Friday nights are busy, especially if there’s a concert at the AMP. She also explained that one of their aims is to target the service industry. She wants Fleet Street to be a place where servers and restaurant managers can come after work to have a meal and a drink. Everything at Fleet Street is made from scratch in their kitchen, and their kitchen stays open very late to accommodate people who may want a late-night meal after work. Fleet Street opens at 11 a.m. and can stay open as late as 3 a.m. on weekends. They have dart boards, and the atmosphere is very conducive for conversation and drinks.

Like Rock’n Dough, Fleet Street has a specialty cocktail menu. There are eight cocktails on the menu. And, since I wanted to give the most accurate depiction of each bar’s selection of drinks, I felt I should probably try a cocktail. I had Wendy pick a cocktail for me. She chose the Erin Rose which is a “fine Irish whiskey, along with fresh lemon juice, grenadine, and soda. Sweet and fiery.” The choice she made was exceptional, and Josh and I were over halfway done (and four drinks in) with our bar crawl. The next two venues involved crossing North Highland and heading into the “Pokémon GO” land that was formerly known as downtown Jackson.

The Downtown Tavern

208 North Liberty Street

Our fourth stop was the Downtown Tavern. I could write an entire article on this place. It has been somewhat of a refuge for me for several years. I’ve made many friends as a result of the Tavern. I’ve listened to some incredible original music from some of those same people. I’ve brought numerous people from work to the Tavern on a Friday afternoon, and we ended up staying until the band shut down.

As Josh and I approached the door, we could hear the music before we even opened it. The crowd was sparse; the air was smoky. Before I made it to the bar, Jeremy Dyer was getting the glass of bourbon I always order ready. I stopped him and asked him to pick something for me that’s been pretty popular recently. He decided on a “Louisiana Dr. Pepper,” which is a shot. I don’t “shoot” a lot of anything, ever, but this drink was very smooth and was made of Southern Comfort, amaretto, Dr. Pepper, and sour mix.

The drink matched the energy in the bar and the music. Josh and I grabbed a table and listened to the duo Blair & Madison cover country songs from the 90s and take requests—even if they didn’t know them. Listening to them reminded me that the Tavern is one of the only places in Jackson that values original music. I’ve spent many Wednesday nights listening to people from Brooklyn to Los Angeles who were passing through Jackson. I became a fan of Christian Lee Hutson and The Bones of J.R. Jones because I saw them play in Jackson on Wednesday. I’ve listened to local artists like Brandon Clifton, Dylan Evans, and The Kernal play their music to a crowded bar at 10:30 p.m. on a Wednesday night. There is so much that this place offers that most people in Jackson have never heard.

If you want the most bang for your buck, come to the Tavern early. Happy hour lasts until nine and the bartenders are some of the best in town. If you want conversation, the regulars are all very friendly. If you want live music, they have it four nights a week. Even on the Thursday night that we were there, the Tavern felt electric. After one more drink, we decided it was time to walk to our last stop.

Miss Ollie's

111 East Lafayette Street

At the bar we asked the bartender to pick out something for us. He chose “Death by Chocolatini,” which seemed fitting as a last drink of the night. I guess anything with the word “death” in it would be fitting for the end of any evening. When I asked the bartender what was in it, he wouldn’t divulge any information. I guess that added some mystery to it, but at that point in the evening I wasn’t too concerned about the amount of alcohol in any beverage I was ordering.

My first sip of “Death by Chocolatini” made me realize that there was most certainly a vodka base to the drink, and that was okay. The drink was very smooth and very easy to drink, which made for a fitting end to our crawl. The atmosphere of Miss Ollie’s is extremely inviting and very favorable for people wanting end their night with a drink and a nice place to sit and have conversation. Miss Ollie’s also doesn’t allow smoking, so it makes it a nice alternative for people who don’t like being around smoke. As Josh and I finished off our last drink, we talked about how different each of these locations had been and that we had been able to visit each one in one night.

A few nights later, I was downtown with some friends and there were people everywhere. The courthouse was lit with colors of the Pokémon teams. There was a line out the door of Woodstock Bake Shop because they had stayed open late. People (including myself) were downtown hunting Pokémon, and I told my friend, “There’s nothing here except virtual creatures and people are everywhere. People will come downtown if we give them a reason to come here.”

I think Jackson is just scratching the surface of what it could be. I truly believe that any thriving community has to thrive downtown. It shouldn’t thrive with chain restaurants and strip malls. And, if it does thrive with those things alone, what does that say about its character? Bar crawls aren’t about drinking, they’re about fellowship. They’re about experiencing different people and different atmospheres. They’re about movement. We don’t ever want to be stagnant on our same bar stool drinking our same drink every night. If people are downtown, businesses will be downtown eventually. Get a group of people together, start at Grubb’s and finish at Miss Ollie’s, and create your own story one night. Experience what Jackson has to offer now because I believe it’s on the edge of something special.

I truly believe that any thriving community has to thrive downtown. . . . If people are downtown, businesses will be downtown eventually.

Gabe Hart is an English and Language Arts teacher at Northeast Middle School. He was born and raised in Jackson, graduating from Jackson Central-Merry in 1997 and Union University in 2001. Gabe enjoys spending time and traveling with his daughter, Jordan, who is eight years old. His hobbies include reading, writing, and playing sports . . . even though he’s getting too old for the last one. Gabe lives in Midtown Jackson and has a desire to see all of Jackson grow together.

Photographer Josh Garcia is a commercial photographer who landed in Jackson in 2008. With a B.A. in English from Union University in his back pocket, he’s abandoned other adjectives for “home” when describing this city. He enjoys reading, writing, photography, and cultivating community around the dinner table. #INFJ