country

The Best Of The Midwest Road Trip Through Indiana, Illinois, and Kentucky

In this whirlwind road trip, you'll traverse three states in four days to experience the best nature, food, breweries, and wineries that this corner of the Midwest has to offer. 

Destinations Explored

1

Indianapolis

2

Louisville

3

Mammoth Cave National Park

4

Shawnee National Forest

Map with locations highlighted

Escape the buzz of Chicago with a road trip south of the city. Along the way, you'll experience local gems (including an old-fashioned soda shop and candy museum) as well as nationally-recognized landmarks. You'll pick berries at a family farm in Indianapolis, sip brandy in Louisville, go cave-hopping in a national park, and so much more. Whether you're in it for the food, drinks, history, or folklore, this getaway will have you covered. 

Key Highlights

Hike to and through the abandoned amusement park of Rose Island

Explore the caves and 53,000 acres of beautiful forest at Mammoth Cave National Park

Hike one of the most picturesque parts of Midwest at the Garden of the Gods

Best Times to Visit

April - October

Sample Trip Itinerary

Day 1

Indianapolis

3 hour and 30 minute drive from Chicago

Accommodation in Indianapolis

Suggested options (actual bookings will vary based on pricing and availability)

Explore Indianapolis below ground in the Catacombs

This guided tour will bring you below ground to the must-visit Catacombs—which, don't worry—don't contain bones or crypts (that we know of). You'll visit the ruins of the imposing Tomlinson Hall, which dates back to 1886 and was destroyed in a fire in 1958, and pass through several brick, barrel-vaulted arches. 

Wander through the gardens at Garfield Park Conservatory

Spanning over 180 acres, Garfield Park is one of Chicago's largest conservatories. This "urban rainforest" tucked away in Chicago's West Side is bursting with verdant greenery from around the world. 

Go berry picking (and stock up on farm-fresh goods) at Anderson Orchard

Anderson Orchard stretches across 150 acres of verdant land that, depending on the season, produces apples, raspberries, a variety of nuts, pumpkins, peaches, pears, and plums. It all started back in 1969 when Paul and Carolyn Anderson set out to design a space that would allow visitors to pick fruit themselves—and to this day, it remains a u-pick property, with the option to purchase fresh produce, cider, and other goods in the shop. 

Taste wines from small local procedures at Butler Winery & Vineyards

Located 10 miles outside downtown Bloomington, Butler Winery & Vineyards is within the northern boundaries of the Indiana Uplands Viticultural Area (AVA) known for producing distinctive, high-quality wines. Six different grape varieties are grown on this seven-acre property, including Chambourcin, Cabernet Franc, Norton, Chardonel, Vidal Blanc, and Vignole—all of which flourish in the midwestern climate. With the exception of Cabernet Franc, all of their grape varieties are French-American hybrid. In addition to tastings, you can enjoy wine by the bottle or glass. 

Day 2

Louisville

2-hour drive from Indianapolis to Louisville

Accommodation in Louisville

Suggested options (actual bookings will vary based on pricing and availability)

Hike through the abandoned amusement park of Rose Island

An early 20th-century theme park, Rose Island was eventually destroyed by a flood just over 10 years after it opened in 1923. Today, you'll find ruins of its former footbridge (which has since been restored), a swimming pool (that has remarkably stood the test of time), and the remains of a stone fountain. To access the site, which is located within Charleston State Park, you'll hike 20 minutes from the nearest parking lot. 

Satisfy your sweet tooth at the old-fashioned soda shop and candy museum

Schimpff’s Confectionery is an 127-year-old candy business in the Jeffersonville historic district. It's been in the Schmipff family since 1891, with the current owners (Warren and Jill Schmipff) living directly above the store. Be sure to visit the manufacturing confectionary, in addition to the candy store, soda fountain, and museum. 

Tour and taste your way through Copper & Kings American Brandy Company

For a taste of Kentucky's rich distilling heritage, Copper & Kings is the place to be. It's here, at this Butchertown-based brewery, that American-style brandy is batch-distilled in copper pot-sills. The non-chill filtered product contains no added sugar, synthetic chemicals, caramel colorants, or boise (aka powdered oak shavings). Be sure to visit the climate-controlled brandy maturation cellar and put on headphones to tune into the songs that sonically age the barrels. From there, head outside to experience the Monarch Butterfly Sanctuary. 

Catch scenic views at Waterfront Park

Waterfront Park is composed of land that was once used for industry and transportation in Louisville. Today, it's a sprawling public space with a great lawn sloping down to the river, where pedestrians can stroll for unobstructed views. 

Day 3

Mammoth Cave National Park

2-hour drive from Louisville to Mammoth Cave National Park

Accommodation in Mammoth Cave National Park

Suggested options (actual bookings will vary based on pricing and availability)

Explore the caves, forests, and lakes at Mammoth Cave National Park

The 53,000-acre Mammoth Cave National Park is home to the longest cave system in the world—with stunning lakes and rivers to boot. Explore the world-class underground (including Hidden River Cave, Lost River Cave, Mammoth Onyx Cave, and Outlaw Cave) in addition to taking advantage of water recreation; there's ample canoeing, fishing, water skiing, and swimming opportunities here. And for all the adrenaline junkies out there, take note of the rollercoasters and zip lines! 

Sip premium wines at Bluegrass Vineyard

Bluegrass Vineyard is a veteran-owned small winery and vineyard that sits atop the limestone rocks of Mammoth Cave, overlooking the rolling hills near Bowling Green, Kentucky. They grow more than 2,000 grape vines, with Cabernet Franc, Chambourcin, Villard Noir, Norton, and Noiret as the red varieties and Traminette, Vidal Blanc, Chardonel, Melody and Vignoles for white. In addition to wine, Bluegrass also grows cherries, raspberries, blackberries, and Crimson Red rhubarb. 

Day 4

Shawnee National Forest Area

3-hour drive from Mammoth Cave National Park to Shawnee National Forest

Accommodation in Shawnee National Forest Area

Suggested options (actual bookings will vary based on pricing and availability)

Drive through the Elk and Bison Prairie

Elk and bison roam free within the confines of this 700-acre enclosure. For the best views, you'll drive in an enclosed vehicle along an 3.5-mile loop. Keep an eye out for wild turkeys, small game, butterflies, and prairie mammals! 

Hike the picturesque Garden of the Gods

With sandstone rock formations and panoramic views, Garden of the Gods is easily one of the most photographed locations in the state. In this scenic recreation area, you can hike, camp, walk the nature trails, or enjoy a picnic. 

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South of Chicago

Indianapolis, Louisville, Mammoth Cave National Park, Shawnee National Forest

Prices start from $740 per person.

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Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

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Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

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Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”

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Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

Testimonial Profile Image

Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

Testimonial Profile Image

Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”