I Petted a Possum at the Southland Street Fair 2026

The Southland Street Fair took over Southland Drive on Sunday, September 27, 2026, from noon to 8 p.m. It's free to get in. The Southland Association puts it on every year, and the city closed the road between Southport Drive and Southview Drive for the day. We got there late in the afternoon. Here's what we saw, ate, and drank.

Parking

I came in the back way. I took Harrodsburg Road, turned right onto Lane Allen, then right onto Southland Drive. There are a handful of businesses just before the police barricade where people were parking. I pulled into an unmarked business lot on Mitchell Avenue, and I saw cars filling the Guardian Savings Bank and HealthFirst Bluegrass lots too. From there it was about a five minute walk to the barricade where the fair starts. If you get lucky you might grab a spot in front of the shops near South of Wrigley, since the barricade sits just past that parking lot entrance.

My wife drove separately and came in from the other end. She parked in the Oleika Shriners Temple lot, and she said people were parking there and at the other businesses on that end just before the road block. So either end works. Pick whichever side you're coming from.

The vendors

The whole street is lined with booths on both sides, more than a hundred of them. A lot of it is craft, and a few stopped me. Consider the Lilies was doing permanent jewelry. Doorcandy by Meg had some really creative fall door hangers. Left Hand Wood Craft had handmade pens. Modern Zen Candle Company had a tent, and so did El Gato Azul, a local t-shirt printing company. There were several jewelry tents, a crochet booth with crochet art, and one selling pet accessories.

I spotted the Ugandan Student Education Fund booth again. I bought from them yesterday at the Kentucky Pop-Ups fall market at Hamburg, so apparently they're working the whole weekend. Small town in the best way.

Food

Bluegrass Caribbean Chefs had a menu of fish sandwiches, pulled pork sandwiches, red beans and rice, plantains, jerk chicken sandwiches, and fish nuggets with fries. Next to them Cardira's Colombian food had a menu I'd call eclectic. The one thing I recognized was the hot dog colombiano, which looked really good. They also had beef or chicken empanadas.

Jasmine Rice was there with Thai food. Taqueria La Princesa had tacos, quesadillas, burritos, and a few other things. Gourmet Grilled Cheese had a whole lineup of different grilled cheese sandwiches. The one that caught my eye was The Blind Pig, a pork barbecue grilled cheese with cheddar and barbecue ranch for dipping, eleven dollars even.

What we ate

We went with Jasmine Rice and I ordered the chicken pad thai to split. Pad thai usually comes in a few levels of heat, but at the fair they were only serving the base level, no heat at all. Chicken, noodles, carrots, onion, green onion, and bean sprouts with a lime wedge on the side, and a sweet taste to it. It was excellent pad thai as always from Jasmine Rice. I highly recommend you go try their food at the restaurant.

The beer garden

The beer garden is set up in the parking lot in front of the Habitat ReStore, the Doo Wop Shop, and the Local Lex Market, right next to Marikka's, and that's where we ate. There's a small stage at the back of the lot. Tahlsound Music Festival put together the music for the whole day, and a band was playing the entire time we sat. People brought their own lawn chairs and set up around the folding tables, so if you've got a chair in the trunk, bring it.

West Sixth, Mirror Twin, and Ethereal were all pouring, plus Beeserker Meadery and Wise Bird Cider, and Castle & Key was there too. My wife grabbed a 32 ounce stadium cup of Hazy But Lazy IPA from Mirror Twin for us to share, and it was a great beer! If they have it on tap at their brewery I highly recommend it. It might top my go-to there, Mos Def. The first cup is twelve dollars and you keep it, then refills are ten.

The pets

There were almost as many pets at this thing as the Woodland Art Fair, and that's saying something. I met Pixie struttin' her stuff down Southland like she owned the road in her ice cream sandwich costume, and I just had to meet her! Then I met Sadie the Possum. She was in a purple dress with a floral top, out on the pavement next to her bubble backpack carrier, and she was happy to be out walking around investigating things. They have cold noses. I can finally check petting a possum off the ole bucket list.