Downtown Owensboro is crawling with excitement—literally! Join us Thursday, May 14 for the 2nd Annual Small Biz Crawl, an all-day celebration of our local businesses and the vibrant heart of our city during National Small Business Month.
Hosted during National Small Business Month, the Crawl invites the community to explore locally owned businesses, discover pop-up vendors, enjoy live music throughout downtown, and support the small businesses that help make Owensboro vibrant.
Whether you stop by for lunch, stay all evening, or make a full day of it, there will be something happening around every corner.
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!
- Big Whiskey’s Owensboro | 11 AM – 1 AM
10% off appetizers, $11 steak & fries, and $15 beer buckets from 6-9 pm! - Bluegrass Music Hall of Fame & Museum | 10 AM – 5 PM
Free museum admission! - Brasher’s Lil Nashville | 4 PM – 2 AM
Open Mic from 6 PM – 9 PM & Karaoke from 9 PM – Midnight! - Byron & Barclay | 11-6 PM
In store specials – come see for yourself! - Colby’s Deli & Cafe | 7 AM – 2 pm
New to the deli?! You get a complimentary cookie! - Colby’s Fine Food & Spirits | 11-8 pm
- Gramps Coffee & Donuts | 7 AM – 3 PM
- Greater Owensboro Chamber of Commerce | 8-4:30 pm
Hosting several member businesses in their office – check out the list below! - Holiday Inn Owensboro Riverfront | Open 24 hours
*Drop your receipts from all participating locations off any time to be entered for cash prizes! - Home2Suites | Open 24 hours
*Drop your receipts from all participating locations off any time to be entered for cash prizes! - John Ross Martin, Realtor at BHG | 10 AM – 6 PM
Complimentary real estate valuations, & strategy conversations!
*Drop your receipts from all participating locations off any time to be entered for cash prizes!
- Kingdom Cords | 10 AM – 6 PM
15% off all clothing (excludes wedding packages)! - Lure Seafood & Grille | 11 AM – 10 PM
Buy $50 in gift cards and receive a free $10 gift card! - Magnolia Mercantile | 10 AM – 6 PM
- Mancave for Men | 10 AM – 5 PM
10% off haircuts and beard trims! - Meadow House Floral + Gifts | 10 AM – 5 PM
10% off all purchases (excludes flowers)! - Mellow Mushroom | 11 AM – 9 PM
- Owensboro Brew Bridge | 3 PM – 10 PM
- Pub on 2nd | 4-10 pm
Singo begins at 7 pm! - SIP Wine Bar | 1 PM – 10 PM
- The Creme Coffee House | 7 AM – 9 PM
$1 off specialty lattes - Willow & Pine Market | 10 AM – 6 PM
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!
- 1885 Cocktail Bar | 12-4 pm
Popping up at The Creme! - Becca Bakes | 8 AM–4:30 PM
Popping up at GO Chamber - BooGi Bliss LLC | 10-5 pm
Popping up at the Pub on 2nd - Boot Barn | 8 AM–4:30 PM
Popping up at GO Chamber - Confetti Boutique | 8 AM–4:30 PM
Popping up at GO Chamber - Hello Pop | 4 PM–8 PM
Popping up at Lure Seafood & Grille - Hill View Farms | 8 AM–4:30 PM
Popping up at GO Chamber - Holes to Go Owensboro | 8 AM–4 PM
Popping up at John Ross Martin Campaign Offices - Hyacinth House | 11 AM–5 PM
Popping up at Bluegrass Music Hall of Fame & Museum - J’s Good Grub | 2:30–4:30 PM
Popping up at Greater Owensboro Chamber of Commerce - M Squared Marketing
Popping up at Pub on 2nd - Maui’s Indoor Theme Park | 8 AM–4:30 PM
Popping up at GO Chamber - Owensboro Health Healthpark | 8 AM–4:30 PM
Popping up at GO Chamber - The Earle | 8 AM–4:30 PM
Popping up at GO Chamber - The Little Healer LLC | 10 AM–4 PM
Popping up at John Ross Martin Campaign Offices
2. Where’s the music?
12 PM – 2 PM: Andy Brasher at Mellow Mushroom
2 PM – 4 PM: Jarred Green at Office of John Ross Martin
5 PM – 7 PM: Dustin & Tristian Taylor at Willow & Pine
6 PM – 8 PM: Paul Montgomery at Big Whiskey’s
6 PM – 9 PM: Rack ’em Leon at Lure Seafood & Grille
7 PM – 9 PM: Joshua Orion at The Pub on Second
3. How do I 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 Home2Suites, Holiday Inn Owensboro Riverfront, or John Ross Martin – Campaign Offices by 10 AM on Friday, May 15. Winners will be announced on Friday!