Prestonsburg Travel Guide

Tourist Guide

Embark on a voyage of country music discovery, hike rugged trails and visit historic battle sites at this popular town in Eastern Kentucky.

Prestonsburg is an attractive small town in the foothills of the Appalachian Mountains. With mountainous scenery, outdoor recreation and a rich country music heritage, it has plenty of fun things to see and do.

Explore the Jenny Wiley State Resort Park. Hike along trails passing through Appalachian terrain. Rent a pontoon boat or canoe for a trip across the park’s 1,100-acre (445-hectare) Dewey Lake. Anglers will relish fishing for bluegill, largemouth, catfish and crappie. During the fall and winter, book your place on an elk-viewing tour. Be sure to bring your camera.

If you enjoy history, visit Middle Creek National Battlefield. During the Civil War a decisive battle was fought here that ended Confederate control of the region. Drive 10 miles (16 kilometres) south of Prestonsburg to see the Battle of Ivy Mountain Monument. The 14-foot (4.2-metre) granite obelisk marks the spot of a famous skirmish between four Union regiments and the heavily outnumbered Confederates.

In the evening, enjoy some of Prestonsburg’s cultural attractions. See a play, musical or comedy show at the Jenny Wiley Theatre. There are also matinee productions for children at various times of the year. The Mountain Arts Centre is home to the Kentucky Opry and occasionally hosts some of the area’s most famous country stars. Dwight Yoakam, Billy Ray Cyrus and Patty Loveless have all performed on its stage.

Prestonsburg is located on a road dubbed the Country Music Highway, so named because many county music stars were born in the area. Finish your trip by spending several days driving along the 144-mile (232-kilometre) road that meanders down Kentucky’s eastern border. Highway markers point to the hometowns of some of the genre’s most famous names.

During your Prestonsburg road trip, stop by some of these places and listen to live bluegrass and county music. Go to Staffordsville for Mountain Homeplace, a working farm that dates back to the 1850s. In Paintsville, tour the family home of country music legend Loretta Lynn.

Comfort Suites Prestonsburg West

Comfort Suites Prestonsburg West

2.5 out of 5
51 Hal Rogers Dr Prestonsburg KY
The price is AU$176 per night from 14 Dec to 15 Dec
AU$176
14 Dec - 15 Dec
includes taxes & fees
Stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
8.4/10 Very Good! (686 reviews)
The staff was the absolute best!! Extremely helpful and so nice.

Reviewed on 26 Nov 2025

Comfort Suites Prestonsburg West
Quality Inn & Suites Prestonsburg next to Mountain Arts Center

Quality Inn & Suites Prestonsburg next to Mountain Arts Center

2.5 out of 5
85 Hal Rogers Drive Prestonsburg KY
The price is AU$163 per night from 3 Jan to 4 Jan
AU$163
3 Jan - 4 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8/10 Very Good! (355 reviews)
Clean room, attentive staff

Reviewed on 17 Nov 2025

Quality Inn & Suites Prestonsburg next to Mountain Arts Center
Super 8 by Wyndham Prestonsburg

Super 8 by Wyndham Prestonsburg

2 out of 5
80 Shoppers Path Prestonsburg KY
The price is AU$104 per night from 28 Dec to 29 Dec
AU$104
28 Dec - 29 Dec
includes taxes & fees
Stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. ...
6.4/10 (511 reviews)
friendly fast front desk personnel.

Reviewed on 12 Nov 2025

Super 8 by Wyndham Prestonsburg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Luxury Estate nestled atop stunning mountaintop golf course!

Luxury Estate nestled atop stunning mountaintop golf course!

2 out of 5
Prestonsburg KY
Stay at this holiday home in Prestonsburg. Enjoy a garden, laundry facilities and patios. Popular attractions StoneCrest Golf Course and Jenny Wiley State Resort ...
10/10 Exceptional! (6 reviews)
This place was s amazing and so was the host Mary and property managers RJ and Angel. Communication was fantastic and the host was very accommodating even making sure we had a waffle maker. The beds were all very comfortable and the sunsets each night were breathtaking. We will definitely be coming ...

Reviewed on 19 Oct 2025

Luxury Estate nestled atop stunning mountaintop golf course!
Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg

Prestonsburg KY
Stay at this holiday home in Prestonsburg. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Archer Park and Samuel May House are located ...
10/10 Exceptional! (8 reviews)
Clean but noisy location late into night

Reviewed on 2 Nov 2025

Cozy Home in Heart of Prestonsburg
New to the area? Stop by and see the most recent bachelor pad on the scene

New to the area? Stop by and see the most recent bachelor pad on the scene

Prestonsburg KY
Stay at this apartment in Prestonsburg. Enjoy laundry facilities and air conditioning. Popular attractions Mountain Arts Center and Archer Park are located ...
The place does not exist. Could not find it. Called the host. Host had phone on not accepting calls. I was in the area for my mom's funeral. Had to scramble to find another place to stay.

Reviewed on 22 July 2024

New to the area? Stop by and see the most recent bachelor pad on the scene
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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