Ten years ago, this stretch of Main Street south of downtown was mostly quiet warehouses. Today it's arguably the most walkable, most-talked-about corridor in the city — and it's about a 15–20 minute walk (or a quick 5-minute drive) from our Chattanooga loft.
Start with coffee at Velo Coffee Roasters or a bagel at Niedlov's, then spend the morning working through Main Street's shops and galleries — much of the neighborhood's art scene lives on building walls and inside coffee shops rather than in formal galleries, so keep an eye out as you walk.
For dinner, Southside's food scene runs deep: State of Confusion for wood-fired dishes and ceviche, Bluegrass Grill for a hearty brunch any time of day, or Main Street Meats if you want a proper butcher-shop dinner. Chattanooga's brewery corridor is concentrated here too — OddStory Brewing, Five Wits, and Wanderlinger are all walkable from one another, so you can hit two or three without moving the car.
When the sun goes down, Southside turns into Chattanooga's best nightlife stretch. Station Street fills with live music and dancing, JJ's Bohemia and Barrelhouse Ballroom book everything from indie rock to local funk, and The Signal draws bigger touring acts if you want a proper show.
Anchoring it all is the Chattanooga Choo Choo — the century-old train station turned hotel, music venue, and restaurant complex that gives the neighborhood its name and its history.
Southside is close enough to explore on foot, far enough from your Highmark Collection stay to feel like a proper night out.
Lewis Jones is the founder of The Highmark Collection, a boutique collection of thoughtfully designed short-term rentals in Asheville, Chattanooga, and Greenville. After a career in leadership roles with IBM and Kyndryl, he created Highmark to bring the same focus on service, detail, and consistency to the guest experience.
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