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Owensboro, Kentucky: How To Enjoy A Perfect Weekend!

Owensboro, KY

Located in the north on the banks of the Ohio River, Owensboro, Kentucky offers attractions and excursions for those willing to stray a little from the Great River Road. As Kentucky’s fourth largest city – behind Louisville, Lexington, and Bowling Green – Owensboro, which is best known for its Bluegrass Music Hall of Fame & Museum, can make for a great detour.

From museums and natural attractions to festivals and excursions, Owensboro is the perfect weekend trip. There is plenty to see, do, and eat in this river town, so plan for a three-day exploration of the city and be sure to check out these great places.

Sullivan’s Supper Club

Start your weekend off right on Friday night with Owensboro’s award-winning, summer-long series of free outdoor concerts held every Friday on the eight-block Ohio riverfront. Running since 1997, the festival started with four concerts and grew into 16 weeks of signature riverfront entertainment. You can head down to the grounds at 5 o’clock when the fun begins and grab food at one of the various food trucks before diving into the excitement.

With seven different stages of entertainment, there will be plenty to do all night long. Hear local and well-known bands play live and take part in the weekly “Toast to the Sunset.” If you’re traveling with family, there are also family events, a kid-friendly street fair, and costume characters to keep everyone entertained. The best part is the weekly event is entirely free, so you don’t have to worry about buying tickets or paying any fees, you can just show up and join in on the fun.

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A great excursion for your second day of exploring Owensboro is the famous Bluegrass Music Hall of Fame & Museum. For a small fee, you can explore the various exhibits on the bluegrass era of music and view the key musicians and events that shaped the genre. A great exhibit to start with is the River Of Sound, which is a self-guided tour that will place the bluegrass movement within history, featuring amazing memorabilia that you won’t find anywhere else.

Other exhibits to visit include the Video Oral History Project Room and the Hall of Fame Room, considered the crown jewel of the museum, where you can visit the greats of bluegrass music who’ve been inducted into the International Bluegrass Music Association Hall of Fame. If you plan on viewing the museum, be sure to check out the concert schedule as live concerts are held often and are a great opportunity to get a little taste of bluegrass music.

The Trempealeau Hotel Logo

A great place to dine in, The Miller House is an upscale but comfortable, family-owned restaurant in Owensboro’s historical downtown district. Built in 1905, this historic home turned restaurant and bar will take you back in time and immerse you in southern history and culture as you enjoy a hearty meal. The seasonal menus featuring Kentucky Proud products and vegetables from the on-property family garden ensure freshness and authenticity creating a wonderful dining experience.

Enjoy a hearty brunch, lunch, or dinner of traditional food with a Southern influence and marvel at the interior of the historic building. After eating, head downstairs to Spirits Lounge in the basement of The Miller House and indulge in Kentucky culture with their signature drinks and bourbons. With over 600 bourbons in stock at a time, Spirits is the largest bourbon bar in western Kentucky and is a great place to try authentic Kentucky bourbon. They also offer a wide variety of signature martinis, mixed drinks, beer, wine, and live entertainment, making this southern experience one you don’t want to miss.

4. River Cafe

The Preservation Station Market and Events Center is a unique Kentucky shopping experience perfect for spending half a day eating some southern comfort food, admiring local art and craftsmanship, and supporting local businesses and vendors. Formerly an elementary school, Preservation Station Market converted the building into a 39,000 sq. ft. retail marketplace with over 60 shops, a gym that hosts community events, and Preservation Station Family Restaurant.

Here you can explore the various rooms and pop-up shops with a wide variety of products for sale. The shops are perfect for gifts of all kinds, as you can find antique and painted furniture, farmhouse signs, wall signs, rustic garden decor, knives, soaps, and Amish goods among many other handcrafted goods. Preservation Station Market is perfect for antique hunters and indoor decor enthusiasts. After a while of looking around and shopping, you can stop at the Family Restaurant and fill up on appetizers, soups, salads, sandwiches, burgers, entrees like catfish, fried chicken and meatloaf, and delicious homemade desserts.

5. Hungry Point Bar & Grill

Your weekend in Owensboro would not be complete without stopping at Green River Distilling Co., a heritage member of the famed Kentucky Bourbon Trail Ⓡ. Built in 1885, the distillery exchanged hands and names many times, until returning to its full glory and original name in 2020, under the ownership of the original owner’s family. Today, the distillery operates independently and is a staple in the community for locals and visitors alike, and is a great place to sip some authentic Kentucky Bourbon.

When you arrive at the distillery, you can grab a hand-crafted specialty drink from the cocktail lounge and prepare to learn all about whiskey production on a guided tour through the grounds. The tour lasts approximately an hour and will give you behind the scenes access into the process of making whiskey, including viewing a grain unloading, barrel dumping, and everything in between. After the tour, you’ll be invited to the tasting room where you can relax and sample their most exquisite bourbon and rye whiskies. Before you go, you can head to the gift shop and grab a souvenir to remember your experience by, from apparel to glassware.

I am a student, aspiring writer, and avid reader of books. My favorite things in the world are my German Shepherds and hiking in Colorado.

Maeve Miller

Writer, River Travel Magazine