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.

Super 8 by Wyndham Prestonsburg
Super 8 by Wyndham Prestonsburg
2 out of 5
80 Shoppers Path, Prestonsburg, KY
Fully refundableReserve now, pay when you stay
The price is ฿2,449 per night from 30 May to 31 May
฿2,449
per night
30 May - 31 May
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 (403 reviews)
"The hotel is run down, needs some updating."

Reviewed on 6 May 2024

Super 8 by Wyndham Prestonsburg
Jenny Wiley State Resort Park
Jenny Wiley State Resort Park
3 out of 5
75 Theatre Ct, Prestonsburg, KY
The price is ฿4,957 per night from 28 May to 29 May
฿4,957
per night
28 May - 29 May
Enjoy free parking, an outdoor pool and a marina.
8.4/10 Very Good! (366 reviews)
"It was a nice area and getaway"

Reviewed on 26 Apr 2024

Jenny Wiley State Resort Park
Comfort Suites Prestonsburg West
Comfort Suites Prestonsburg West
2.5 out of 5
51 Hal Rogers Dr, Prestonsburg, KY
The price is ฿3,650 per night from 9 Jun to 10 Jun
฿3,650
per night
9 Jun - 10 Jun
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 ...
8.4/10 Very Good! (537 reviews)
Great stay
"It was great. Everyone was very friendly and helpful to use. Well stay there again."

Reviewed on 18 May 2024

Comfort Suites Prestonsburg West
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.
'homeplace' w/ Yard - 10 Mi to Jenny Wiley!
'homeplace' w/ Yard - 10 Mi to Jenny Wiley!
3 out of 5
Hagerhill, KY
Stay at this 3-star cottage in Hagerhill. Enjoy free parking, patios and in-room fireplaces. Popular attractions Paintsville Golf Course and Loretta Lynn's Home ...
8/10 Very Good! (1 review)
"Really liked the old house feel but very noisy by road"

Reviewed on 13 Aug 2023

'homeplace' w/ Yard - 10 Mi to Jenny Wiley!
Downtown Paintsville Vacation Rental!
Downtown Paintsville Vacation Rental!
3.5 out of 5
Paintsville, KY
Stay at this 3.5-star cottage in Paintsville. Enjoy free parking, in-room fireplaces and air conditioning. Popular attractions Paintsville Golf Course and U.S. ...
Downtown Paintsville Vacation Rental!
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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