Road Trip from Chicago to Red River Gorge, Kentucky

Why Red River Gorge, KY?

Rock Climbing/rappelling – Red River Gorge or The Red as it is called, is known for the best climbing crags in the nation, perfect for rock climbing/rappelling.
Underground Kayaking – an exhilarating experience of Kayaking in almost pitch dark in a forgotten underground mine, accompanied by chilling temperatures even when its 90 degrees outside the cave.

Underground Kayaking, Courtesy Gorge Underground

Red River – A water fest for the kids: boasting of activities like Cliff jumping, Kayaking, River Tubing.
Scenic Overlooks, trails, scenic drives, streams.
Bonus: Cumberland falls is couple of hours away from Red River Gorge area and the only place in the Western Hemisphere where you can see a moonbow in action.

How to Plan your visit?

•  For accommodation, we stayed here via Vrbo and couldn’t recommend it more – the host was super helpful, house was well-equipped and epitomized Southern country side living experience to the hilt.

IMG_20220714_231440272 (1)The house glimmered under the July 14 Supermoon on our first night

• Run through this indispensable emergency checklist.

• Run though the tech essentials to turbo-charge your road trips.

•  Choose your activities and places to visit. We did the following in a 3 day trip: Underground Kayaking, Natural Bridge via Skylift, Red River Jump Rock, Sheltowee Trace Trail (we cheated and hiked to suspension bridge which is 0.3 miles and came back, rather than doing full 12 miles),  Cumberland Falls (one of the rarest places in the world where you can see the moonbow), Eagle Falls Trail.

•  Other noteworthy activities: Ziplining, staying at these dome town tree houses, Kentucky Reptile Zoo, Chimney Top Overlook, Whistling Arch Overlook, Rock Bridge Trail.

Inside the unconventional ‘dome’ tree house, courtesy rrgcabins

The network of ‘dome’ tree houses, courtesy rrgcabins

•  Other Useful links: check the region maps and other useful info here.

Our Trip from Naperville

July14-17, 2022

Road Trip
Naperville to Stanton, KY.
440 miles, GPS ETA was 7 hours, we made it in 8 hours with a couple of breaks.

Route to the Red is mostly flat until you reach Daniel Boone National Forest 

Ohio River, as seen while driving

We reserved this cottage and thoroughly enjoyed it. The house was squeaky clean, kitchen was well-equipped, had plenty of open spaces and was a few miles away from most touristy places. The basket ball hoop, hot tub and indoor air hockey table amped up the fun factor for the kids.

A well equipped kitchen is a must for a vacation home

The fire pit had auto-on solar lights

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Kids made good use of the board games

Day 1 – The Natural Bridge, Miguel Pizza and the Cumberland Falls

The Natural Bridge

We took the skylift to reach the top of the bridge. You could hike as well but it looked a bit strenuous.

There was a short hike to gain access to the Natural Bridge.


The views from the bridge were exhilarating, it had numerous vistas along the way.

As seen from the Natural Bridge – you can see Lovers Leap at a distance

Tip: Don’t miss the Lovers Leap overlook, you would find the trailhead right by the skylift drop-off area. You will get the unrestricted panoramic view of the Natural Bridge from the overlook.

We climbed down to the base of the bridge which had a very narrow alley.


Once at the base, were amazed to view the Natural Bridge in all its might.


There were a mesh of hikes from the base, we randomly chose the point-and-back Battleship Rock Trail.


There were some mystical craters along the way and we didn’t risk peeking what’s inside them.


The Battleship Rock was a bit of an anti-climax on why it was named that way, may be due to the craters? Please use the comments if you know the answer.

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Miguel Pizza

I was told by a colleague that gorging on Miguel Pizza after the hike/rock climb is almost a ritual. We put Miguel Pizza’s sky-high reputation to the test.

The pizza joint was swarmed with visitors and had ample spaces both inside and outside.


We had couple of pizzas and sandwiches and found the food and the cordial staff, worth all the adulations and the gazillion 5-star reviews. Truly worth the visit!

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Cumberland Falls

We headed over to Cumberland falls to gaze the moonbow in the night. We caught a quick glimpse of it before heading over to a hike nearby, since we still had a few hours before the moonbow could be visible.

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The calm water stream before it descends fiercely

Cucumber Falls – As seen from an overlook on Eagle Falls Trail

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Cucumber Falls – As seen from another overlook

Eagle Falls Trail

We hiked down the Eagle Falls Trail to experience the natural swimming hole besides the waterfall.

The hike was a little challenging, with stairs, rocks, large boulders to finally reach the waterfall.

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It took us about an hour to reach the waterfalls.

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Here’s how it looked in action:

The kids jumped right in to enjoy the swimming hole.


Note: the water is a little deep at places so gotta be a little careful.

Moonbow at Cumberland Falls

After packing up at Eagle Falls, we went back to the city for the dinner and then came back at midnight to Cumberland Falls. This is one-of-a-kind experience and the only one in the Western Hemisphere.


The nature had other ideas though – the night was riddled with completely dark skies, we couldn’t get a glimpse of the moonbow and we bailed out at 1:30 AM.


Day 2 – Red River Jump Rock, Suspension Bridge and Underground Gorge

Nada Tunnel

We went via Nada Tunnel, which was an extremely narrow road tunnel with one-way traffic only and bulging rocks from all sides. Worth the experience.

The tunnel entry, courtesy Cliffview Resort


Red River Gorge Scenic Byway

We took the route highlighted in red from Stanton to experience the scenic byway. You can find more details here.

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Scenic Byway map, courtesy: FHWA

The views were rewarding indeed. Pretty sure the fall foliage would be incredible here.

As seen while cruising through the scenic byway

Red River Jump Rock

You have to park the car close to the Sheltowee Trace Trail and take a very short hike to the jump rock. There are limited parking spots so worst case you might need to park on the highway and walk to trailhead.

The hike was gentle with ample shade

We spent a couple of hours at the jump rock. The kids had a blast taking a plunge over and over again.


The whole place had a carnival-ish vibe with music and cheers for the jumpers. You could swim around or kayak as well.


Suspension Bridge

We ambled over to the suspension bridge from the jump rock. You just need to continue along the Sheltowee Trace Trail.

The suspension bridge was worth the short hike, the right sort of wobbly which gave kids (and some adults) a bit of a scare without being dangerous.


The Red River, as seen from the bridge

We turned back to the parking lot post the bridge.


The Road Trip Back

Took roughly 8 hours with few leisurely breaks. Had a very satisfying lunch at the Waffle House on our way back.

PXL_20220716_004140261-EFFECTSSo Long, Kentucky!

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