Things to do in Kentucky, United States: The Best Lookouts

August 4, 2021 Mikaela Didonna

Famous for Bourbon Country and horse farms, civil war battlefields and beautiful natural parks, Kentucky offers a delightful mix of experiences. You might begin in Lexington, where the 1200-acre Kentucky Horse Park is a popular attraction. The university adds exciting sports, impressive art and a vibrant student/professor population to the city. Louisville is similar, where renowned Churchill Downs hosts the annual Kentucky Derby and the Belle of Louisville, the nation’s oldest steam-driven river paddlewheeler, hosts enchanting lunch and dinner cruises along the beautiful Ohio River. Next, head south to visit Mammoth Cave National Park for a day of touring the cave (the world’s longest known cave), hiking and canoeing on the Green River. Paducah, Berea, Bowling Green – so many places to explore and enjoy!
Restaurants in Kentucky

1. Hogg Overlook

Pine Mountain Rd, Whitesburg, KY 41858 https://www.kentuckytourism.com/whitesburg/natural-attractions/nature-wildlife/pine-mountain-overlooks
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5.0 based on 1 reviews

Hogg Overlook

The Pine Mountain Overlooks were a labor of love, created in order for people to be able to come from all over to enjoy the beauty that Letcher county Kentucky provides. \r\n

2. Civil War Fort at Boonesboro

1250 Ford Road, Winchester, KY 40391 +1 800-298-9105 http://www.civilwarfortatboonesboro.com
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3.5 based on 15 reviews

Civil War Fort at Boonesboro

The earthwork fortification was built by Union Soldiers to defend the ford and ferry at Boonesboro. A scenic trail provides a beautiful view of the Kentucky River. Self-guided tour. A moderately strenuous, wooded one-mile loop trail that provides panoramic views of the Kentucky River Valley. Pet friendly.

Reviewed By charlesbC6079KL

The gun battery never saw action and is actually at Ford, Kentucky, to guard the crossing here on the Kentucky River. Stiff walk up a hill to the gun battery but well worth the climb. Nearby is Fort Booneboro and Kentucky River Museum.

3. The Summerhouse

100 Martin St, Greenville, KY 42345-1571 http://tourgreenville.com/attractions/the-summerhouse/
The Summerhouse

4. Falcon Overlook

Pine Mountain Rd, Whitesburg, KY 41858
Falcon Overlook

Located where the old Falcon Inn used to be, this overlook is dedicated to Community Trust Bank. The elevation at Falcon Overlook is 2,557 feet. Etched in the concrete is the date 1948 and the name Doyle. This location was an overgrown building foundation with only a chimney standing.

5. Combs Overlook

Hwy 23, Jenkins, KY 41537
Combs Overlook

Combs Overlook, named for well-known Kentucky State Police Trooper Bennett David Combs, who died in August 2014 after a long illness. He was 55. The overlook gives views of Jenkins' beautiful mountains, Raven Rock Golf Course and one of the most beautiful place to watch a sunset in the Appalachian mountains.

6. Little Shepherd Trail

Kentucky Highway 1679, Whitesburg, KY 41858 https://www.facebook.com/pages/Little%20Shepherd%20Trail/166220526884414/
Little Shepherd Trail

Located in scenic southeastern Kentucky, parts in Letcher and Harlan counties the Little Shepherd Trail is a curvy mountain road that twists and turns more than 350 times as it leads to the most stunning views in the state. The windiest road in Kentucky is not for the faint of heart, but your heart will surely fall in love with this magical drive in our beautiful state.

7. Cliffside Overlook

Pine Mountain Rd, Whitesburg, KY 41858
Cliffside Overlook

8. Hemlock Overlook

Pine Mountain Rd, Whitesburg, KY 41858 +1 606-634-1814 [email protected] https://www.discoverletcher.com/
Hemlock Overlook

Standing at an elevation of 2,377 feet, this overlook gives guests an overwhelming 180-degree view of Letcher County’s mountain range. Hemlock Overlook provides guests with custom railing and an observation deck. It also has picnic tables, where those passing through can rest, eat and enjoy the view.

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