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
The price is £59 per night from 5 May to 6 May
£59
per night
5 May - 6 May
Stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free WiFi and free parking. Our guests praise the helpful staff in their reviews. ...
6.4/10 (401 reviews)
"Staff was nice."

Reviewed on 10 Mar 2024

Super 8 by Wyndham Prestonsburg
Comfort Suites Prestonsburg West
Comfort Suites Prestonsburg West
2.5 out of 5
51 Hal Rogers Dr, Prestonsburg, KY
The price is £92 per night from 12 May to 13 May
£92
per night
12 May - 13 May
Stay at this business-friendly hotel in Prestonsburg. Enjoy free breakfast, free WiFi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (531 reviews)
Nice simple stay
"The interiors are very new, which was a nice amenity. The pool area was clean and it was nice to sit by the pool and relax a little bit. The room was clean and the sofabed was helpful and a nice additional space to gather then sleep on. We could hear the neighbor in the shared room a little bit but ..."

Reviewed on 22 Apr 2024

Comfort Suites Prestonsburg West
Jenny Wiley State Resort Park
Jenny Wiley State Resort Park
3 out of 5
75 Theatre Ct, Prestonsburg, KY
The price is £99 per night from 1 May to 2 May
£99
per night
1 May - 2 May
Stay at this 3-star hotel in Prestonsburg. Enjoy free parking, an outdoor pool and a marina. Popular attractions Jenny Wiley State Resort Park and StoneCrest ...
8.4/10 Very Good! (358 reviews)
"The property itself is very good, considering that it is in a State Park. Don't expect brand new city hotel cleanliness or newness. But it is in the middle of a beautiful nature area. The restaurant staff need better training to be better hosts. They seem to take their own sweet time to even acknowledge ..."

Reviewed on 22 Apr 2024

Jenny Wiley State Resort Park
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.
Perfect Lake Getaway!!
Perfect Lake Getaway!!
Prestonsburg, KY
Stay at this houseboat in Prestonsburg. Enjoy a TV, a kitchen and 2 bedrooms. Popular attractions Jenny Wiley State Resort Park and StoneCrest Golf Course are ...
Perfect Lake Getaway!!
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 WiFi, 1 bedroom and a combined bath/shower. Popular attractions Mountain Arts Center and Archer Park are located ...
New to the area? Stop by and see the most recent bachelor pad on the scene
The Red Dog Cottage In The Woods w/ Hot Tub
The Red Dog Cottage In The Woods w/ Hot Tub
Williamson, WV
Stay at this cottage in Williamson. Enjoy free WiFi, on-site parking and a garden. Popular attractions Hatfield McCoy Trail - Buffalo Mountain Trail System and ...
10/10 Exceptional! (26 reviews)
The perfect cottage!
"My wife and I stayed at the Red Dog Cottage for our wedding anniversary trip. The cottage and surrounding property were beautiful and meticulously cleaned and groomed. My wife and I enjoy riding ATVs and this location was perfect for that, being only .5 mile from the Hatfield McCoy trail entrance. ..."

Reviewed on 25 Mar 2024

The Red Dog Cottage In The Woods w/ Hot Tub
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.

Popular places to visit