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 ฿3,292 per night from 16 Jul to 17 Jul
฿3,292
฿3,733 total
16 Jul - 17 Jul
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! (638 reviews)
"Loved the pool, location of hotel, responsive and professional staff"

Reviewed on 22 Jun 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 ฿3,256 per night from 16 Jul to 17 Jul
฿3,256
฿3,692 total
16 Jul - 17 Jul
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 ...
7.8/10 Good! (307 reviews)
"Convenient location with easy access. Noisy traffic at times. Friendly staff and a very good breakfast. Reasonable price. Room was a bit small."

Reviewed on 18 Jun 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 ฿2,185 per night from 20 Jul to 21 Jul
฿2,185
฿2,409 total
20 Jul - 21 Jul
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 (489 reviews)
"There was an awful smell in the hallway out there alone but the room was great"

Reviewed on 8 Jun 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.
Near Scenic Parks: Convenient Home in Prestonsburg
Near Scenic Parks: Convenient Home in Prestonsburg
3 out of 5
Prestonsburg, KY
Stay at this 3-star business-friendly cottage in Prestonsburg. Enjoy free parking, a marina and air conditioning. Popular attractions Samuel May House and Archer ...
Near Scenic Parks: Convenient Home in Prestonsburg
'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 family-friendly cottage in Hagerhill. Enjoy free parking, patios and in-room fireplaces. Popular attractions Preston Park and Paintsville ...
"Really liked the old house feel but very noisy by road"

Reviewed on 13 Aug 2023

'homeplace' w/ Yard - 10 Mi to Jenny Wiley!
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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