48 Hours in Owensboro, Kentucky

As the birthplace of Bluegrass music and Kentucky’s BBQ mecca, there’s so much to do on a weekend getaway to Owensboro, Kentucky. Being only two hours away from Louisville, it’s a perfect day trip for us which is why we’ve explored this town so much! For most, it probably isn’t a day trip, but Owensboro is also a perfect town to stop on a cross-country road trip!

A LITTLE HISTORY: Owensboro was founded in 1797 by Bill Smothers, and has since grown to be the 4th biggest city in Kentucky. Traditionally a coal mining community and with consistently good weather in Owensboro – it quickly transformed into an agricultural community. Owensboro is now known for it’s quaint Southern charm and BBQ!

Why would you stop in Owensboro??

Interstate-64 goes from Norfolk, Virginia (central on the Eastern seaboard of the US) all the way to St. Louis, Missouri. That means on a cross-country road trip, I-64 will take you the most central direct route and 1/3 of the way across the US, and Owensboro is only 40 minutes from the interstate. When we’re on a road trip, finding towns like Owensboro to stop in for the night is so important. There’s a ton of good food, interesting history to explore, and a great river walk to stretch your legs. Let’s explore all of the best things to do in Owensboro, Kentucky!

Looking for more Southern travel inspiration? See some of our other favorite posts from around the South.

• Your Full Guide to Rocket City: Huntsville, Alabama
• Louisville’s Chic NULU Neighborhood Guide
• What To Expect In Bell Mountain Georgia

Can’t Miss Festivals in Owensboro, Ky

We mentioned that Owensboro is a BBQ mecca for Kentuckians, as well as the home of Bluegrass music. There are a few incredibly fun festivals to attend, even if you’re just passing through.

International BBQ Festival

Always the second weekend in May, the International Barbecue Festival in Owensboro is a conglomeration of all of the delicious things you need surrounding BBQ! Friday and Saturday on the Ohio Riverfront in downtown Owensboro, there are tons of activities including a Backyard Barbecue Cookoff for the best chicken, mutton, and burgoo.

A little explanation of what these barbecue terms mean. Mutton is the tender meat of adult sheep. Burgoo is a thick southern-style stew made with barbecue sauce, meat, and vegetables – traditionally served with corn-bread!

• In 2021 there is a pared-down version of the festival called the BBQ Block Festival. Some of the normal activities won’t be going on but it will still be fun!!

The International BBQ Festival serves ’10 tons of mutton, 1,500 gallons of burgoo, and 5,000 chickens’ all while 80,000 people attend!

ROMP Festival

The biggest music festival in Owensboro, and one of the biggest music festivals in Kentucky is ROMP Festival!! Produced by the Bluegrass Music Hall of Fame, the festival is typically held every year in June.

• In 2021, ROMP Festival will be held the second week of September!

Besides an incredible Bluegrass Music Lineup – the festival is also home to workshops for songwriting, clogging, yoga, and Bluegrass 101. ROMP Festival is basically the hippie Bluegrass Kentucky version of Coachella, complete with organic farm-to-table food vendors!

Get our full guide on how to pack for music festivals here!!

Festival Address: Daviess County’s Yellow Creek Park – 5710 KY-144, Owensboro, KY 42303

• Friday After 5 – if you’re considering what to do in Owensboro during a road trip – try stopping in on Owensboro’s friday night summer concert series! Friday After 5 is a 17 week series, dating back to 1997 with more than 70,000 people attending every year! 7 stages, tons of restaurants, and it’s totally free! (Finding free things to do in Owensboro like these live shows makes it super easy to make a pit stop on your cross country road trip!)

***Big-O Music Fest – Right after college Shelbs went with some gal pals to Big-O-Fest! It was how we got to know Owensboro, and it was one of the best festivals we’d been to in Kentucky. Newer artists like Moon Taxi, Jake Owen, Cole Swindell were all pretty amazing to see! If you’re looking for what to do in Owensboro, we’re sorry to report that this festival has been cancelled until further notice! This music festival stopped after 2017 – we’re leaving a note out there in case you’ve heard about it!!

No matter what festival you get to, when the weather in Owensboro is nice, and you’re walking along the river in this charming small town – you’ll have a great time!

Free Things To Do In Owensboro

The best free things to do in any city are to walk and get to know the outdoor attractions. Owensboro has quite a few free things to do, starting with taking a walk downtown in Owensboro’s Historic District. You’ll run right into Owensboro’s Riverfront Park, which has gone through a major renovation in the last few years!

• Smothers Park – Named the ‘Top Playground In The World’, there is so much to see at this park on the Owensboro Riverfront! We walked by with our friends just to take a peek at the enormous tree sculptures at the entrance to the park and we were totally blown away! Fountains, a waterfall, giant animal sculptures, a concession stand, free wifi – as well as being handicapped accessible – make it the coolest riverfront we’ve ever seen!
  Address: 199 W Veterans Blvd, Owensboro, KY 42303

The riverfront park is the same park you’ll find the ‘Friday at 5’ free concert series! If you’re looking for free things to do in Owensboro – we love the idea of taking a stroll downtown, grabbing ice cream from the concession stand at this park, and then continuing on to listen to some live music! If the weather in Owensboro stays pretty for the evening, You’ll have a true southern small town experience that Friday night!

Reid’s Apple Orchard

Another of the great free things to do in Owensboro is visit Reid’s Apple Orchard! Allan Reid came to American from Scotland in 1873, and actually helped pioneer technology for pruning and production of peaches and oranges!!

Anything you buy at Reid’s Orchard obviously won’t be free. That being said, what is free is exploring the farm, your produce picking experience, and the Apple Festival in October!

• Picking Produce: Spending the day picking out fruits and veggies from the fields would be so relaxing, and your only cost will be the produce you want to take home! From peaches, apples, blackberries, strawberries, tomatoes etc. – you can make just about any pie you want after a day at Reids!
• Reid’s Orchard Market: If you’re not in the mood to pick your own fruits and veggies, Reid’s is going to be the place where you can get all of your fall staples inthe fall, as well as all the necessities for your charcuterie boards! (Because there really is nothing better than a sampler of meats, cheeses and relishes during a picnic break while you’re on the road?)

The best time to visit Reid’s Apple Orchard if you’re from out of town is October! With over 100 craft booths, more than 20 food booths, carnival rides and more – the Kentucky Tourism Board named the Apple Festival in the Top 10 Festivals in Kentucky!

**Also named one of the top 20 events in the Southeast USA by the Southeast Tourism Society which covers 11 states!!

Murals in Owensboro, Kentucky

If you’re looking for a few free things to do in Owensboro, start by walking through town and doing a little street art hunting!

Not only do we love walking a city to really get to know it – we love seeing street art. This first set of murals is on the corner of Simply Chic Home Accents! The Kentucky Map, the Be The Change Lion and these colorful wings by Owensboro artist, Paige Owens, are all Instagram worthy and easy to find.

• Shelbs is pictured there with on of our favorite Owensboro locals – little Miss Channing Smith! Her mom, Jackie Smith is a close friend and owns an incredible hand-made jewelry company – Jackie Blue Handmade!

Address: 101 W 3rd St, Owensboro, KY 42303

We love finding murals and understanding their significance in shaping a community. Both of these murals are so important to Owensboro’s local culture!

• Blue Musical Instruments Owensboro Mural – The Chamber of Young Professionals (CYP), led by Austin Casebolt, an Owensboro art teacher, spearheaded the project to bring more art and tourism to the city. The blue musical instruments are an homage to Bluegrass music‘s humble beginnings in Owensboro. So beautifully done – this is one of our favorite murals in town!
  Address: 215 E 2nd St, Owensboro, KY 42303
• ‘The Image Hunter’ Osprey Mural – This giant osprey is part of a 20 series project by Italian street artist, Hitnes, as a tribute to the book ‘Birds of America’ by John James Audubon.
  Address: 100 St Ann St, Owensboro, KY 42303

the vintage Coca Cola Mural

The last mural we found that we really love is this Coca-Cola mural downtown. It says ‘relieves fatigue’ like it’s a health tonic? Not just a boatload of sugar that gives the drinker a momentary surge in energy before an epic afternoon slump? Vintage ads always give us a good laugh!

Address: 210 Allen Street, Owensboro, Kentucky 42303

Please tag us in any of your selfies while you’re out exploring. We love seeing when other people find murals too! If you’re looking for more murals to explore in Kentucky, head to Louisville where we have over 100 gorgeous murals!

Other Fun Things To Do In Owensboro, KY

After reviewing the best free things to do in Owensboro, there are a few fun attractions worth your hard-earned dollars! One of the cleanest theme parks near Kentucky, the brand new state-of-the-art Bluegrass Music Hall of Fame & Museum, and touring the area’s best whiskey distillery!

• Bluegrass Music Hall of Fame & Museum: Visiting the Bluegrass Museum should be on top of everyone’s Owensboro Bucket List – especially if they’re from Kentucky! General admission gets you into the museum to explore all of Bluegrass music’s history with revolving exhibitions as well as the Hall of Fame! Their top events include the ROMP Festival, The KY State Fiddle Championship, and the Nashville Songwriter Convention!
  Address: 311 W. 2nd Street, Owensboro, Kentucky 42301
• Owensboro Museum of Fine Art: Only just now celebrating it’s forty year benchmark, the Owensboro Museum of Fine Art has become a home to many unique collections of Native American Art and Appalachian Art. Both groups were central in the creation of creating the Kentucky we know and love today!
  Address: 901 Frederica Street, Owensboro, Kentucky 42301
• Holiday World & Splashin’ Safari: One of the cleanest theme parks we’ve ever been to – as well as the most fun! With free drinks and free sunscreen all day – enjoying both the theme park and the water park makes for an awesome day only about 40 minutes from Owensboro!
  Address: 452 E. Christmas Blvd., Santa Claus IN 47579
• The Rockport Lincon Pioneer Village – Where President Lincoln lived during the first 14 years of his life – this pioneer village preserves a few historical buildings from that time. The most fun part of the experience is the actors playing historical roles throughout the preserved village!
  Address: 928 Fairground Drive, Rockport, Indiana 47635

Green River Distilling Co.

A little history on the Green River Distilling Co.: Started in 1885 – J.W. MucCulloch started distilling what he called ‘the whiskey without a headache’! The company grew but then couldn’t make it through prohibition which lasted from 1920-1933. (Prohibition was just a bad time for all Kentuckians?! We love our bourbon and all things distilled really?!)

After the distillery was sold, and changed hands many times through the years, it was only added to the historic Kentucky Bourbon Trail in 2018. Before 2020, this distillery was known as the O.Z. Tyler Distillery, but the company decided to change its name back to Green River Distilling Co. honoring its original heritage.

• Green River Distilling Tours: $15 Monday – Saturday and then a smaller Sit & Sip Monday -Saturday.
• Cocktail Lounge: Monday through Saturday 10 AM-3 PM. (Weird times to grab a cocktail but hopefully the hours open further after quarantine stops!)

When considering what to do in Owensboro, make sure you add the farthest west point of the Kentucky Bourbon Trail to your list! Find tour information here.
Address: 10 Distillery Road, Owensboro, KY 42301

Best Hiking in Owensboro

One of the first things we do when traveling anywhere is trying to find a hiking trail nearby. When we were looking for what to do in Owensboro, we knew we were gonna need to find a few good trails! Beyond just having a giant German Shepherd, we try to stay active to earn our indulgences while we travel!

There aren’t a ton of mountains or state parks around Owensboro, but they do have a few trails and botanical gardens!

• Trail of Dreams; A 3.2-mile loop featuring a rope bridge!
  Difficulty: Easy
• Martin, Levee, Outer, and River Loop: A 4.0-mile easy loop through the wetlands of the area. Also, remember to bring bug spray! If you’re walking through the wetlands any time from March – October – you’re in Kentucky’s mosquito season!
• Rudy Mines Trail – This trail is 4.8 miles and a little on the harder side. The perks are that it’s not well traveled and therefore very quiet. (Our favorite kind of hikes!) There are also a number of streams on the trail meaning that your dogs will have plenty of water on the trail!

WESTERN KENTUCKY BOTANICAL GARDENS: If you’re just in a mood to take a walk – the Western Kentucky Botanical Gardens are open from 9 AM to 6 AM every day! These stunning gardens are a gem in Western Kentucky, and when the weather in Owensboro cooperates – it’s even a favorite for the locals!!

**The first Saturdays of every month are free admission!

Address: 25 Carter Road, Owensboro, KY 42301

Where to Shop in Owensboro

What we love about a city like Owensboro is that it’s basically a perfect setup for enjoying a nice day out walking, shopping included. It’s been our experience that most small towns have at least a few local boutiques? Owensboro being the fourth largest city in Kentucky has plenty of them and many are in the main historic district downtown!

***Window shopping is also a perfectly acceptable free activity in Owensboro and beyond. You never know what you might find! We’re not big fans of materialism but supporting local is so much better than supporting a big chain.

Walkable Boutiques Downtown

• Byron & Barclay: Your one-stop shop for upscale basics and great travel clothes in Owensboro. If we need something in town – this is the first place we go! Men’s and women’s clothing all in the same store makes it an easy stop for us!
  Address: 121 E 2nd St #100, Owensboro, KY 42303
• Adam & Sons Men’s Fine Clothiers: Custom-made men’s clothes as well as shoes, ties, and leather goods.
  Address: 401 W 2nd St #105, Owensboro, KY 42301
• Shelley & Friends: One of Owensboro’s best hair salons and boutique all in one!
  Address: 128 E 9th St, Owensboro, KY 42303
• Willow & Pine Boutique: If you ever need a wedding gift, house-warming gift, or even teacher gifts? The Willow & Pine Boutique is where you need to go!
  Address: 126 W 2nd St, Owensboro, KY 42303

Other Chic Southern Boutiques Around Owensboro

• Bella Regazza Boutique: A really cute and upscale women’s boutique you can also shop online!
  Address: 2684 Frederica St, Owensboro, KY 42301
• Bushay’s – Another great Southern men’s boutique.
  Address: 4431 Springhill Dr. Suite C, Owensboro, KY 42303
• Peacocks & Pearls: A really cute boutique out of Lexington that also made their home in Owensboro, Kentucky. You can also shop them online!
  Address: 4431 Springhill Dr, Owensboro, KY 42303
• Boutique 54: Great for plus-size finds!
  Address: 3245 Mt Moriah Ave #5, Owensboro, KY 42303
• Hot Mess Mama Boutique: Best place to find gifts specifically for moms in Owensboro!
  Address: 3830 KY-54 #102, Owensboro, KY 42303

If you’re looking for a way to enjoy the pretty weather in, Owensboro – grab something to eat, do a little shopping, then head to the riverfront to enjoy all of the free fun things Owensboro has to offer!

Best Restaurants In Owensboro

We’ve already mentioned that Owensboro is the hotspot for Kentucky BBQ. If you’re in town looking for a place to grab a bite – make sure you try burgoo! (It should be required for anyone traveling through the South to try it at least once? Also pimento cheese… there is no such thing as too much Pimento Cheese!) Anyways – here are the top three BBQ joints around town that consistently fight for top marks at the International BBQ Festival!

• Moonlight Bar-B-Q Inn – Family-owned since 1963, Moonlight Bar-B-Q has grown into a 350 person capacity restaurant, a full catering business, and a processing plant serving BBQ’ed goods in a four-state area. You could say they’re doing well!
  Address: 2840 West Parrish Avenue Owensboro, Kentucky, 42301
• Old Hickory – The oldest BBQ establishment in Owensboro, old Hickory BBQ has been in business since 1918! Still family-owned, there are 6 generations of the Foreman family working to keep Old Hickory running. They must be doing something right to have been in business for over 100 years!
  Address: 338 Washington Avenue, Owensboro, KY, 42301
• Ole South BBQ: Celebrating more than 25 years in business, Old South BBQ is home to a laid-back diner vibe, and catering to events all over Western Kentucky.
  Address: 3523 Hwy 54 E., Owensboro, KY 42303

Other Southern Staple Non-BBQ Restaurants:

• Bubba Gandy Seafood Market – Pick up an entire seafood/crawfish boil to take home or on a picnic!
  Address: 3600 Frederica St suite k, Owensboro, KY 42301
• The Miller House – Part bourbon bar, part upscale restaurant, The Miller House sits at home in a historic mansion downtown in Owensboro. ‘Spirits’ is their best-kept secret! A swanky bourbon bar in the basement and perfect for date night!
  Address: 301 East 5th Street, Owensboro KY 42303
• Colby’s Fine Food & Spirits: Open since 1987, this charming Southern staple in downtown Owensboro serves seasonal dishes and has over 700 4.5 star reviews!
  Address: 204 W. Third Street Owensboro, KY 42303
• Bar Louie: An aweome spot for outdoor dining downtown.
  Address: 234 Frederica St, Owensboro, KY 42301

All of these local staples are incredible stops for anyone looking to enjoy good Southern cuisine in Owensboro!

Best Coffee Shops in owensboro, KY

• The Cottage Farm & Baking Co.: The cutest little coffee shop and cafe on the outskirts of town! Not only has the family who owns The Cottage been in Owensboro for 170 years. They’ve also made it their mission to offer baked goods, local produce, and herbs to their community.
  Address: 6869 State Route 56, Owensboro, KY 42301
• The Creme Coffee House: Fresh baked goods like cheesecake, brownies, and cinnamon rolls are served daily along with yummy deli sandwiches! The Creme Coffee House also has one of the most Instagram-worthy patios and interiors – it’s our pick for the best coffee shop in the city of Owensboro! (See the first picture of this post!)
  Address: 109 E 2nd St, Owensboro, KY 42303

Where To Stay In Owensboro

There are plenty of great places to stay in Owensboro, especially if you’re looking to head there for festivals!

Campgrounds:

• Diamond Lake Resort – the prettier of the two campgrounds in Owensboro and an awesome option for festival-goers! There are 270 full hookups for campers as well as regular lots for rough campers. They also have go-carts, a movie theater, and hotel rooms for those not interested in camping!
  Address: 7301 Hobbs Road,  Owensboro, KY 42301
• Windy Hollow Campground – A perfect campground for the summer! With a lake for swimming including a slide and diving board, plus a beach and mini-golf!
  Address: 5141 Windy Hollow Road, Owensboro, KY 42301

To find a great hotel within an easy distance from Owensboro’s main attractions, we frequently use Booking.Com. Simply type in your dates below and you’ll find a number of options available for your trip.

(If you’re booking around festivals – make sure you plan ahead and book early!)

P.S. Thinking about sharing your Owensboro adventures on Instagram? Get all of our favorite Kentucky quotes and sayings here.

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Until next time friends,

Thanks for sharing!