The Ultimate Owensboro Weekend Getaway

Updated February 2025

Owensboro is just over the Ohio River from Indiana. An Owensboro weekend is filled with Bar-B-Q, Bluegrass, and Bourbon. They have a fabulously revamped downtown and riverfront with eateries, coffee shops, parks, museums, and hotels. It is only 30 minutes from Holiday World and Splashin’ Safari, one of my top things to do in Indiana. It’s a great destination for families, couples, and those visiting Santa Claus looking for various lodging and dining options.

With a bragable arts and music scene, I left Owensboro feeling like I had visited Nashville, Tennessee. Except without the hustle and bustle of big city traffic, noise, and cost. Follow my itinerary for an Owensboro weekend getaway!

A special thanks to Visit Owensboro for hosting my trip. All opinions in this article are my own.

Day 1 in Owensboro

After a day at Holiday World and Splashin’ Safari in Santa Claus, Indiana, we drove to Owensboro and grabbed dinner at Old Hickory Bar-B-Q. The historic Old Hickory is a local favorite that has operated for six generations. It’s a no-frills establishment that started in 1918 and is known for its famous mutton, award-winning bar-b-que, and cooking sauce.

Mutton is an Owensboro delicacy with a story behind it. Daviess County was home to many German Immigrants who raised wool for sheep and used the meat to make mutton. It was a staple in the 1800s and remains on menus to this day—unique to Owensboro. I had never tried mutton before this trip, and I’m glad I did. It was tender and juicy. You have to give it a try!

After dinner, we visited Owensboro’s Sassafras Tree, the world’s largest. It is located just off Frederica Street in front of the State Farm building. It is a quirky roadside historic sight over 100 feet tall and over 21 feet wide.

For the weekend, we stayed at the polished Holiday Inn Owensboro Riverfront, located directly on the banks of the Ohio River. Sitting within walking distance of the Bluegrass Hall of Fame & Museum, Smothers Park, and restaurants. After checking in, we took a stroll along the river walk and enjoyed the hotel’s outdoor seating area.

Day 2 in Owensboro

I was excited about our first morning stop: breakfast at Gramp’s Coffee & Donuts. Upon entering the cafe, we were greeted by Gramp himself. Before my visit, I had read fellow Holiblogger Suburban Turmoil’s blog about Gramps, so I knew the story and recognized his face. Gramp’s Coffee & Donuts is a family-run donut shop celebrating life and community through delectable croissant donuts, coffee, and espresso drinks.

We polished off those donut calories with a self-guided tour of the Owensboro Museum of Fine Arts River Artes public art. The tour includes 21 pieces of art throughout Owensboro. You can grab a tour brochure with a map at the Visitor Center, 215 East 2nd Street, or the Owensboro Museum of Fine Arts (free admission), 901 Frederica St, Owensboro.

Smothers Park is another downtown riverfront location that we checked out. It’s so cool that in 2015, Landscape Architect’s Network named it the top playground in the world. In addition to the enormous playground and water play area, there are signature fountains, overlooks, picnic areas, the Shelton POW Memorial, RiverFront swings, a concession stand, and restrooms.

For lunch, I dined at the City Walk of Owensboro, a cozy eatery tucked between several of the City’s outdoor murals. Inside the City Walk, murals of the city line the walls. Locals suggested trying the Kentucky Hotbrown and Bourbon-Glazed Pork Loin, both delicious and satisfying. After that meal, I needed a nap. We grabbed a cold drink from the eclectic and artsy Creme Coffee House before returning to the hotel.

(I’ve heard somewhere that drinking coffee 20 minutes before a nap helps you sleep better. That somewhere is from your favorite travel writer, who likes to fit in by visiting every coffee shop in every town she visits.)

After dark – dinner and nightlife

For dinner, I made reservations for the Spirits Lounge at The Miller House. This historic landmark has been restored into three levels of dining, and reservations are highly recommended. The Spirits Lounge is located in the basement and is very popular because it contains the largest Bourbon Bar in Western Kentucky. It’s aesthetically pleasing and romantic, with exposed brick walls, candlelit tables, live music, and a mysterious charm. Tip: Get the Southern Sampler; the cheese torte is a “chef’s kiss.

The night ended with a popular Owensboro event: Fridays After 5. This family-friendly, free event is held every Friday from 6 p.m. to midnight for 16 weeks every summer. Stages with bands entertain throughout the night. Spectators can walk along the Riverfront to visit each stage, vendors, and food trucks. There was a stage at the Holiday Inn so that we could enjoy music directly from our hotel!

Day 3 in Owensboro

Red Swing Coffee was my morning motivation for our last day in Owensboro. I was impressed with the number of local coffee shops within walking distance of the hotel. I’m one happy camper when I have a latte in my hand. Red Swing had great lattes and these unique and delightful bubble waffles. We chatted with Brandon, half of the husband-and-wife duo owners. As he told me the story behind the name Red Swing, I began to see a theme in Owensboro. Family and community involvement are important to these businesses; their stories are personal and have meaning and purpose.

The Bluegrass Hall of Fame & Museum was one of the stops I was most looking forward to. It did not disappoint. After a self-guided tour of the museum exhibits and hall of fame, we poked around the Pick & Play section at the museum’s beginning. In this area, anyone is welcome to pick up and play a variety of instruments. Executive Director and musician Chris Joslin played a few songs. It was a great experience!

The Bluegrass Hall of Fame & Museum also participates in Fridays After 5, is a concert venue, and hosts the annual ROMP Fest.

Daviess County is located along the Kentucky Bourbon Trail and is home to the Green River Distilling Company – the fourth-largest independent bourbon distillery in the United States. I do not often write about distilleries in my articles; my writings typically focus on coffee and food. But I love a good piece of history. The historical Distillery Tours are educational and allow you to go behind the scenes of the 28 acres of production and into original buildings from 1885 (bourbon tastings are optional).

The Western Kentucky Botanical Garden is a slice of horticultural heaven. It’s an oasis of 13 themed gardens, the historic Weatherberry home, and several event spaces. The World’s Largest Basket, the “Bouquet for Marjorie,,” is an iconic public art piece in the garden. We took a self-guided tour of the gardens and saw it dressed up for a wedding later that day. This was our last stop before grabbing lunch and heading home.

Speaking of lunch, The Cottage Farm Stand caught my eye for coffee, but their menu also enticed us to grab food here. They have originals like “The Owensboro” burger and “The Cottage Latte” on their menu. I love themed menu items – I have to get them. So naturally, these were both ordered. The burger came in a Niko’s Bakery Brioche Bun, which was a bonus since we didn’t get a chance to try Niko’s during this visit. Two thumbs up for The Cottage and their sweet cafe.

That’s a wrap for our weekend getaway in Owensboro! What places would you like to visit in Owensboro? Did I miss a spot I should check out next time? Let me know in the comments below!

Itinerary Locations:

Other places to check out:

Moonlite BBQ Inn
Niko’s Bakery & Cafe
Homeplace of Bill Monroe
Owensboro Outdoor Murals tour