Tucked just beyond the heart of downtown Knoxville but still a part of the buzz, the Old City invites you to look closer and immerse yourself in one of East Tennessee’s most character-rich neighborhoods. You’ll find 100+ year-old original brick pavers down Jackson Avenue, historic warehouses turned creative hubs, and a love of all things local, proving the Old City is tailor-made for travelers craving authenticity over itinerary checklists. Here’s how to spend a weekend living like a local – savoring, strolling, and discovering at your own pace.
First things first – snacks! Pick up a few gourmet goodies from Red Panda Grocery on Central, Knoxville’s answer for all your bodega needs. From there, you’re good to go!
Since you’re at Red Panda, the shortest way to get some grub is literally next door at Kaizen. Think Asian fusion from fried rice and steamed buns to curry and Thai wings.
You might be surprised to find another izakaya option just across the street in Fin-Two Alehouse. Lean into the ramen options, sushi, and yakitori.
Down the street at the corner of Central and Jackson, you’ll find Boyd’s Jig & Reel, a pub with authentic Scottish fare and live music. It’s got an enormously impressive collection of whisky – we’re talking over 1,000 different varieties! More on the building itself in the walking tour under #13 below.
Get lucky with a Friday night concert at The Mill & Mine. Otsu Dumpling is conveniently next door for small plates before the show.
Start your day with a slow walk and a strong cup of something warm (or cold, you iced coffee fiends!).
Old City Java is the heartbeat of the block, one of the OGs of Knoxville’s coffee scene since 1991. Locals camp out here with sketchbooks, poetry, or newspapers – nobody’s in a rush (how’s that for “Counter Culture”, eh?). Enjoy murals in the adjacent alley while savoring some savories (the baked goods inside come from their sister coffee shop and bakery Wild Love).
Looking for light? Awaken Coffee has the prettiest southeast-facing windows around, lending an airy feeling to this row of former warehouses built around 1890-1910. They’re known for their creative concoctions throughout the year, and serve Quills Coffee out of Lexington, KY. The Dogwood Arts Gallery is next door for some art viewing, but keep in mind they are closed on the weekend.
Find Five and Hoek at the edge of the Old City on Magnolia. They are a specialty coffee roaster focused on roasting ethically sourced coffee, direct trade coffee, and the top 1% of coffee in the world.
Walk it off with a self-guided Old City architecture tour (TLDR; skip ahead to Saturday Afternoon):
Stick to the Old City area with #5-13 on theDowntown Knoxville WalkingTour. Access the map and listings digitally or pop into Visit Knoxville for a printed guide. While you’re out and about, look out for “ghost signs” – those faded hand-painted ads from a century ago – along Jackson and Central Streets. The below is borrowed from that tour, written by our friends at the Knox Heritage (italics are editor-added commentary, accurate in 2025):
#5 Jackson Terminal 205 West Jackson Avenue – A long wooden fertilizer building built on this site in the 1860s prefigures the current structure which was built in the late 1880s with almost identical dimensions, likely on the foundation of the older fertilizer building. During the era of the East Tennessee, Virginia, and Georgia Railroad – one of the South’s major railroads of the post-Civil War period – it served as a freight depot, as it would after 1894 for Southern Railway. Today, you’ll find multiple business here: Pour Taproom, PostModern Spirits, Able Trade, and event space. We’ll come back to these!
#6 JFG Coffee Company Building 200 West Jackson Avenue – Originally the home of Bowman Hat Company, this five-story structure was built in 1924. It served for most of its history as a roasting plant for JFG Coffee beans. The building became JFG’s headquarters in 1926. JFG Coffee Company was founded in Morristown in 1882 by James Franklin Goodson as a wholesale grocery company. JFG was one of the best-known regional coffee roasters and marketers of ground coffee, tea, mayonnaise, and peanut butter. JFG was acquired by Louisiana’s Reily Foods Company (maker of Luzianne Tea) in 1965. This location closed in 2005. The building’s Romanesque influences were typical of buildings involved in the jobbing trade that developed during the latter part of the 19th century. The building was renovated into residences in 2009 by Dewhirst Properties. On the street level, you’ll find Curious Dog, some of the best hot dogs (and sandwiches) you’ve ever had in your life!
#7 Hayes-Henson Building 130 West Jackson Avenue – Haynes Henson Shoes, which had its headquarters on Gay Street, built its wholesale house here around 1907. The partnership of J.P. Haynes and James A. Henson claimed to have shoes in stores in every state in the South. Henson died not long after occupying this building, and his widow funded the construction of nearby St. John’s Lutheran Church in his memory. In the 1990s, architect Buzz Goss and Old City resident and advocate Harold Duckett renovated the building as Jackson Ateliers. Today, visitors can expect to see the RED Gallery, curated by the adjacent Robin Easter Design, featuring the work of regional artists and typically open on First Fridays. (Check out our Guide to First Friday here!)
#8 The Daniel 118 West Jackson Avenue – This building, one of Knoxville’s more exuberant examples of the Richardsonian Romanesque vogue in architecture of the late 1880s, has served clothiers for most of its history. By 1896 it was the headquarters of the Powers, Little apparel manufacturing company. (Reversing the usual pattern, Powers, Little had its executives in Knoxville, but its factory on Bleecker Street in New York.) The company was later known as Little Brothers. In 1936, Georgia tailor John H. Daniel set up shop here and though he lived in Knoxville only a short time before moving to Virginia and a new career in politics, he founded a durable business that remained in the building for more than 75 years, gaining international renown for its fine men’s suits. Today, it’s home to lofts for lease (also known as The Daniel) with the Old City Athletic Club, a boutique gym, on the ground level.
🥪 Lunch
Work your way over to Depot Avenue (over the railroad tracks to the north). Now would be a great time to grab lunch! Your whole crew will have options aplenty inside Marble City Market, Knoxville’s first food hall. It’s got everything from Afghani cuisine to zesty fries and hot chicken.
👟 Back to It – Let's Get Those Steps In!
#9 Southern Railway Depot 318 West Depot Avenue – The Southern Railway Depot was designed in 1907 by Southern Railway architect Frank P. Milburn of Columbia, South Carolina. The Freight Depot was renovated and converted to office space in the late 1980s by the architectural firm of Bullock Smith and Partners who undertook a major renovation in 1989.
#10 Southern Railway Passenger Station 306 West Depot Avenue – Built for the Southern Railway on the site of East Tennessee’s first train station, this 1903 building originally featured a loft, weathervane and clock tower. The Station was designed by noted train station architect Frank P. Milburn. The terminal illustrates the prominence of Knoxville as a wholesaling center. At the time the terminal and depot were built, Knoxville was the third or fourth largest wholesaling market south of the Ohio River, a position brought about by the completion of rail lines that linked Knoxville with the towns and crossroads markets in its region.
#11 White Lily Building 222 North Central Street – The home of J. Allen Smith & Company, the building has come to be known as the White Lily Building, after the company’s most famous product, White Lily Flour. The original central section of the White Lily building dates to 1885. In 2007, J.M. Smuckers Company bought the White Lily brand and, in mid-2008, closed the Knoxville mill. Dewhirst Properties purchased it in 2011 and converted it into an apartment building. White Lily Flour is currently produced by Smuckers in two Midwest plants. Today, there are more lofts (also called White Lily) to be found here with Riverside Tattoo Co. on the main floor.
#12 Patrick Sullivan Saloon 100 North Central Street – Patrick Sullivan was an Irish immigrant and Union veteran who lived in this building with his large family and ran a saloon on the main floor. Sullivan’s saloon was first located near the Southern Railway Depot but moved to the present building in 1888. At the time, Sullivan’s was an anchor of the saloon district called the Bowery, which included as many as 30 saloons along a halfmile stretch of Central (roughly from the railroad to the river), as well as numerous other legal and semi-legal businesses catering mostly to travelers and working class men. In later years, the saloon was run by Patrick’s colleague Dan Dewine, who used his saloon earnings to help establish St. Mary’s Hospital, East Tennessee’s first Catholic hospital. After it closed in 1907, when the city banned saloons, the building hosted other businesses, including a boarding house, an upholstery business, and most notably Armetta’s Ice Cream, which flourished here in the 1920s and ‘30s – their advertisement is still visible in fading paint on one exterior wall. It was reborn as Sullivan’s Saloon on St. Patrick’s Day, 1988, after being restored by Kristopher Kendrick. Sullivan’s has been called the best surviving example of a downtown saloon in the southeastern United States. Today, this same beautiful building houses Lonesome Dove, celebrity chef Tim Love’s third flagship restaurant featuring an upscale “urban western” menu.
You’ll now be turning on the 100 block of Central, which was famous by 1900 for housing East Tennessee’s highest density of saloons (10 of them competed with each other on this sidewalk in 1907) but also, for many years, as one of Knoxville’s busiest business blocks. It sometimes hosted as many as 61 businesses, many of them run by Greek, Italian, Lithuanian and other European immigrants.
#13 Stevens/Manhattan Building 101 South Central Street – Druggist John H. Stevens opened his shop at this corner in 1894, and his pharmacy remained in the building until about 1914. After a period as a photographic studio, around 1925 the building hosted the Manhattan Cafe, run by the Greek immigrant Cavalaris family. With the end of Prohibition in 1933, it became an especially popular beer hall. It had a lively reputation and expanded into adjacent space to handle the crowds. After the beer hall closed in the early ‘50s, the building served as a storeroom and suffered a serious fire before it opened as one of the Old City’s first successful night spots, Manhattan’s, in 1987. In recent years, it has hosted Knoxville’s first known Scottish-themed bar, the Jig & Reel.
All that walking has earned you a brew…or two! You’ve got more choice than you have time, so here are a few ideas to get you started with neighborhood pubs and casual hangout spots:
We said neighborhood pub, right? The Public House on Magnolia is exactly that. Expect a chill vibe with a touch of hidden urban oasis. If you’d rather see and be seen, the Urban Bar & Café sits prominently with its patio facing the corner of Central and Jackson.
Ooh, Monkey’s Bar at Central and Depot is another great pick. If you’re lucky, you’ll see the namesake Monkey (the resident Golden Retriever) when you order your drink.
To catch a game before the game, you’ve got the Local Smokey and the Old City Sports Bar.
Negroni enthusiasts need look no further than Brother Wolf, and its adjacent Osteria Stella for tasty tapas.
Begin an elegant evening at Kefi, where Greek small plates meet Tennessee ingredients. Top notch cocktails will transport you to the Mediterranean.
A casual nosh for dine-in or to-go? Look no further than Good Golly Tamale!
We mentioned Pour Taproom and PostModern Spirits earlier, these two share an enormous patio in the heart of the Old City. The former will have you sampling every kind of brew around (just tap your bracelet to the wall), and the latter will showcase some of the best of Tennessee Whiskey Trail. Head further up Jackson for more tasty Tennessee Whiskey Trail action at Knox Whiskey Works.
⚾ Saturday Evening: Take Me Out to the Ball Game + Late Night Music and Fun
America’s favorite pastime awaits at Covenant Health Park! Catch a Knoxville Smokies Game (baseball) or One Knox/One Knox Women (soccer). Find a game that fits into your schedule, and plan around it for the perfect weekend.
After the game ends and as the sun dips, the rhythm shifts. The Old City glows with music, dancing, and late-night eats to celebrate that post-game win.
Barley's Taproom is the first option you’ll come to outside the stadium, serving up wood-fired pizza and a massive craft beer list typically with live music and open until 2pm on Fridays and Saturdays.
Beloved bar meets creative, independent, and experimental music and performance. That’s no other than the Pilot Light, a beacon in the Old City for 25 years!
Open until 1pm, the Alchemy Lounge & Cigar Bar is a luxury cigar lounge and cocktail bar with a 1920s-era hunting lodge aesthetic with leather couches and chairs, a large walk-in humidor, and Spanish cedar walls.
Nightclub seekers have several options all down the block on Central. Hannas Café, Southbound, Wagon Wheel, and Carleo’s all have their own sound and scene.
Davinci’s Pizzeria and Calzones is the end to your evening eats – open til 3am on Fridays and Saturdays!
Ease into Sunday with brunch at some of Knoxville’s favorite hot spots!
Babka to make your bubbe blush? Blini for your bestie? Instagram-worthy icon? Oh yeah, it’s here at Potchke. This concise menu will get you out of bed, and you better, because it’ll be busy in no time. Order a pastrami or a lox bialy and start the day right.
The classic brunch pick has to be STIR. Expect all your favorites plus, bloody marys, mimosas, and craft cocktails in the dining room or on their dog-friendly patio. Southern Grit is another great option, offering biscuits, fried green tomatoes, and pimento cheese dip.
A beer with brunch…Balter Beerworks has you covered. This mechanics garage turned gastro-dream is perfect for a bennie and a brew.
After brunch, celebrate The Maker City spirit with independent boutiques, one-of-a-kind finds, and gallery gems.
The Back Pocket blends vintage fashion and upcycled designs. Look closely for this shop, they’re below ground level on the northwest corner of Jackson and Central. Contra is another fun find for the vintage hunters!
Bethie Lou’s Fabulous Gift Store is exactly that, a fabulous place for fabulous gifts! You’ll find funny things, locally made things, and eclectic things of all kinds. Boldure Gifts is another charming stop (pun intended), with jewelry and handcrafted roses.
If you’re extra lucky, you might be here for an Old City Market, happening on West Jackson on First Fridays AND the third Sunday of the month. The perfect time to get handmade goodies to remember your visit! Another First Friday stop to add to your list is Able Trade, a membership based shared wood and metal shop designed for the industrial entrepreneur. When they’re open, they invite visitors to pop in and chat with these makers creating in real time.
Wrap up your visit with something that is quintessentially Knoxville: Pretentious Craft Co.! It’s the only place in the world where you can drink a beer brewed on site, from a glass handblown on site, and see the entire process from start to finish!
❤️ Why We Love It
In Knoxville, there’s no rush. No checklist. Just conversations with coffee shop regulars, run-ins with local artists, and slow-paced discoveries on every block. Whether you’re traveling solo, with a partner, or bringing friends along for the ride, the Old City invites you to be here not just see here.
If you ask around, locals will tell you what we’re telling you now: the Old City isn’t a destination.
It’s a neighborhood – and for a weekend, it’s yours!
Author
Kristen Combs
Kristen Combs is the Director of Communications & Social Strategies for Visit Knoxville. With an extensive knowledge of Knoxville as a tourist destination, Kristen is also the author of 100 Things to Do in Knoxville Before You Die, published by Reedy Press and available in the Visitors Center Gift Shop. Find Kristen on Instagram at @100thingsknoxville.
