Things to do in Whitesburg, Kentucky (KY): The Best Lookouts

February 10, 2022 Jasper Kershner

Whitesburg is a home rule-class city in and the county seat of Letcher County, Kentucky, United States. The population was 2,139 at the 2010 census. It was named for C. White, a state politician.
Restaurants in Whitesburg

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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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. 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.

3. 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.

4. 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.

5. Cliffside Overlook

Pine Mountain Rd, Whitesburg, KY 41858
Cliffside Overlook

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