Downtown Owensboro is crawling with excitement—literally! Join us Wednesday, May 22 for the first-ever Small Biz Crawl, an all-day celebration of our local businesses and the vibrant heart of our city during National Small Business Month.
Whether you’re sipping coffee, shopping for gifts, enjoying live music, or snapping selfies, there’s something for everyone. And yes, there are cash prizes on the line.
Here’s your full guide to crawling like a pro:
1. Who’s Participating?
This year’s Crawl features a fantastic mix of Downtown OBKY businesses and pop-ups hosted by downtown locations. All purchases from any of these registered participants count toward the $1,000+ in cash prizes—so shop, eat, and explore freely!
Downtown Businesses
These brick-and-mortar businesses call Downtown Owensboro home and they’re ready to welcome you in!
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Brashers Lil Nashville (4 PM–2 AM)
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Byron & Barclay (11 AM–6 PM)
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Don Mario’s (11 AM–9 PM)
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Ghostly Productions (12 PM–7 PM)
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Goodwood Brewing (11 AM–9 PM)
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Gramps Coffee & Donuts (7 AM–3 PM)
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Kate & Waverly Home (10 AM–5 PM)
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Kingdom Cords (10 AM–6 PM)
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Lure Seafood & Grille (11 AM–10 PM)
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Mellow Mushroom (11 AM–9 PM)
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Pub on Second (4 PM–10 PM)
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Red Swing Coffee (7 AM–5 PM)
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RiverValley Behavioral Health at The Crowne (8:30 AM–6 PM)
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RYco Jewelers (10 AM–5:30 PM)
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Simply Chic Home, Gift & Floral (10 AM–7 PM)
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SIP Wine Bar (1 PM–Midnight)
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The Brew Bridge (3 PM–10 PM)
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The Creme Coffeehouse (7 AM–9 PM)
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Willow & Pine Market (10 AM–8 PM)
Guest Pop-Ups
These incredible local businesses don’t have a brick-and-mortar downtown, but thanks to their generous hosts, they’re popping up just for the Crawl!
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Aesthetic Dental & Skin Institute (9 AM–3 PM)
Hosted by Gramps -
Bonnie Rae Boutique (10 AM–5 PM)
Hosted by Simply Chic Home, Gift & Floral -
Bluegrass Bourbon Dessert Bar (4 PM–Sellout)
Hosted by Pub on Second -
Dano’s Cigar Lounge (4 PM)
Hosted by Pub on Second -
Formation Clay (5 PM–8 PM)
Hosted by Willow & Pine -
Hyacinth House (11 AM–6 PM)
Hosted by RiverValley Behavioral Health at The Crowne -
Jackie Blue Handmade (5 PM–8 PM)
Hosted by Willow & Pine -
Krazy Kat Studios (5 PM–10 PM)
Hosted by The Brew Bridge -
The Little Flower Farm (4 PM–8 PM)
Hosted by Willow & Pine -
Whipt Creations LLC (4-8 PM)
Hosted by SIP Wine Bar -
20/20 Walker Consulting (8 AM–6 PM)
Hosted by RiverValley Behavioral Health at The Crowne
2. Live Music & Entertainment
Here’s who you’ll catch live and loud across Downtown OBKY:
- WBKR’s Chad & MKat (Live remote broadcast from 11 AM–1 PM)
You’ll find this dynamic duo roaming downtown, stirring up fun and interviewing folks on the fly. They may not be live music, but they’re absolutely live entertainment. - Andy Brasher (12–2 PM at Mellow Mushroom)
- Brad Smith & Scott Riches (4–6 PM at Willow & Pine)
- Paul Montgomery (6–8 PM at The Pub on Second)
- Joshua Orion (4–6 PM at Byron & Barclay & 6:30 PM at Lure Seafood & Grille)
Wherever you crawl, the soundtrack’s going to be good.
3. Crawl Cam Challenge
We want proof you crawled. Snap selfies at any (or all!) of the following spots during the Crawl for a chance to win some great prizes from downtown and maybe even a feature on our socials!
- If you can catch them… a selfie with WBKR’s Chad & MKat as they roam downtown stirring up fun during their live remote
- Turning in your receipts at Hampton Inn Riverfront
- With one of the musicians
- In front of your favorite Downtown OBKY shop
- With something tasty you bought (food or drinks!)
- With the Blue Bridge in the background
- With your favorite downtown mural
Post your pics with #SmallBizCrawl and tag Downtown Owensboro and/or GOEDC’s socials to enter.
4. Turn In Your Receipts to Win CASH
Every receipt = one entry! Make a purchase at any participating business (downtown or pop-up), then turn in your receipts for a shot at $1,000 in cash prizes:
- 1 Grand Prize: $500
- 5 Additional Prizes: $100 each
How to enter:
Drop your receipts off at the Hampton Inn & Suites Downtown Owensboro/Waterfront by 10 AM on Friday, May 24. Winners will be announced shortly after during a live video on the Downtown Owensboro Facebook page!