Your Two-Day Itinerary for Owensboro

Owensboro is the perfect place to spend a weekend getaway. Whether you’re on a cross-country roadtrip to a city like St. Louis (only three hours away) or Nashville (only two hours away), or you’ve just decided to get out and explore the great state of Kentucky, our northwestern city should absolutely be a destination on your radar. 

In a matter of 48 hours, there is so much to do, see, hear and experience in Owensboro. We’ve crafted a two-day itinerary for those wanting to get in as many sights, sounds and smells as possible. 

Day One: 

Once you arrive in Owensboro, you’ll probably want to drop off your luggage at your hotel of choice. We have so many amazing hotels to choose from here – many of them new! You can find a list of hotel properties here, including two that overlook the Ohio River and are located in our beautiful downtown area. 

Now that you’ve started settling in, it’s a great time to get out and try something new. That’s the whole reason you traveled to a new place, right? 

One of the top spots on your list should definitely be Green River Distilling Co. After launching their flagship bourbon (to great reviews, mind you) in 2022, there’s never been a better time to take a tour of our historic bourbon distillery. You can book a tour for $20 Monday-Saturday at 10 a.m., noon and 2 p.m. These one-hour tours include a tasting of three different bourbons produced at the facility and are led by some of the best tour guides in the state. 

While you’re in the downtown area, there are some great places to check out for lunch. We often hear the question, “Where should we eat?” from tourists. And honestly, it depends on what you like! But you can find amazing lunch and dinner options at Mellow Mushroom (known for its pizza and craft beer), The Famous Bistro (Greek cuisine – amazing food, but a little pricier), Fetta (pizza by the slice – including mashed potato pizza), Don Mario’s (Mexican cuisine and amazing outdoor dining), Lure Seafood and Grille (seafood on the riverfront), The Brew Bridge (a brewery featuring southern-style cuisine), The Creme Coffee House (coffee and great breakfast/lunch sandwiches) and Colby’s (American cuisine). 

After lunch, head downtown to Smothers Park to explore one of the greatest playgrounds on the planet, along with a beautiful riverfront that includes fountains, a walking trail and Bluegrass music played on speakers along the way. 

This is also a great chance to check out The Bluegrass Music Hall of Fame and Museum (when planning your trip, check their schedule to see if a concert will be playing!) in downtown Owensboro, as well as Western Kentucky Botanical Garden. 

At night, grab a ride on the Downtown Trolley to Brasher’s Lil’ Nashville for some live music. Stop in at the Pub on Second for a beer or a specialty martini before. If you’re visiting Owensboro over the weekend, you don’t even have to leave downtown for a night of entertainment, as Friday After 5 and Downtown Live will both be in full swing on Friday night. 

Day 2: 

After seeing all that downtown Owensboro has to offer, it’s time to get out and explore a little further! 

Head to Preservation Station for breakfast and one of the coolest shopping trips you’ll ever take, as this retail venue is housed in a former elementary school and includes more than 60 different shops! 

While you’re out that way, stop by The Cottage for a quick lunch on your way back to town, and take the bypass to the other side of Owensboro (only a 15-minute drive) to Reid’s Orchard, famous for its annual Apple Festival. You can shop at the onsite market for all kinds of farm grown goodies you just won’t find anywhere else. 


When you get back to the city, be sure to swing by the Owensboro Museum of Fine Art for one of the best art museums in the state of Kentucky. Not only is admission free (though donations are appreciated), but one of the largest folk art galleries in the country can be found right here. 

And once you’ve entered city limits again, it’s time to try our world-famous barbecue for dinner. Whether you swing by Moonlite Bar-B-Q Inn, Old Hickory Bar-B-Q or Ole South Bar-B-Q, you will not be disappointed by the array of mutton, pork and ribs we offer here in Owensboro. Our annual Bar-B-Q Festival is famous for a reason, and these restaurants have garnered worldwide fame for their delicious flavors. 

If your second day in Owensboro is a Saturday, head back downtown to enjoy Live on the Banks, a free summer outdoor concert series held at Smothers Park from 7-9 p.m. You can grab a drink from any establishment and ask for a plastic green cup to carry it in to and from different sights within The District, if you prefer. This is your chance to take in the color-changing lights on our downtown bridge while you sip a cocktail and enjoy everything that makes our city so wonderfully unique and beautiful.