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Prestonsburg
Travel 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 kilometers) south of Prestonsburg to see the Battle of Ivy Mountain Monument. The 14-foot (4.2-meter) 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 Theater. There are also matinee productions for children at various times of the year. The Mountain Arts Center 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-kilometer) 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.

The Landmark Hotel
The Landmark Hotel
3.5 out of 5
190 S Mayo Trail, Pikeville, KY
The price is CA $108 per night from Jun 14 to Jun 14
Situated in Pikeville, this hotel is within 1 mi (2 km) of Pikeville Family Medicine Clinic, University of Pikeville, and Eastern Kentucky Exposition Center. ...
4/5Very Good! (179 reviews)
"There wasn't anything I didn't really like. It was a very enjoyable stay. Would come again."

Reviewed on May 30, 2021

The Landmark Hotel
Holiday Inn Express Hotel & Suites Pikeville, an IHG Hotel
Holiday Inn Express Hotel & Suites Pikeville, an IHG Hotel
2.5 out of 5
476 S. Mayo Trail, Pikeville, KY
The price is CA $142 per night from Jul 4 to Jul 4
Situated in a rural location, this hotel is within 2 mi (3 km) of Pikeville Family Medicine Clinic, University of Pikeville, and Eastern Kentucky Exposition ...
4.2/5Very Good! (369 reviews)
Funeral stay
"Employees are great! Just is a little run down in rooms. Needs updated. for price .."

Reviewed on Feb. 3, 2021

Holiday Inn Express Hotel & Suites Pikeville, an IHG Hotel
Jenny Wiley State Resort Park
Jenny Wiley State Resort Park
3 out of 5
75 Theatre Ct, Prestonsburg, KY
The price is CA $120 per night from Jun 15 to Jun 15
Situated in Prestonsburg, this hotel is 0.1 mi (0.1 km) from Jenny Wiley State Resort Park and within 6 mi (10 km) of StoneCrest Golf Course and Archer Park. ...
4.3/5Excellent! (204 reviews)
"This has a great location right on the lake. Wonderful place for a weekend get away"

Reviewed on Jun. 7, 2021

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.
Jmeez Cabin Rentals
Jmeez Cabin Rentals
Williamson, WV
The price is CA $152 per night from Jun 16 to Jun 16
Situated in Williamson, this cabin is within 1 mi (2 km) of The Coal House and Williamson Memorial Fieldhouse. Tug Valley ARH Regional Medical Center is 1.8 ...
5/5Exceptional! (1 review)
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Reviewed on Sep. 24, 2020

Jmeez Cabin Rentals
Jmeez Cabin Rentals
Jmeez Cabin Rentals
Williamson, WV
The price is CA $182 per night from Jun 16 to Jun 16
Situated in Williamson, this cabin is within 1 mi (2 km) of The Coal House and Williamson Memorial Fieldhouse. Tug Valley ARH Regional Medical Center is 1.8 ...
3/5 (1 review)
Main road
"We booked this cabin last minute and did not research it, we had no way of knowing it was 20 feet from a main busy road. There were tvs in the bdrms with no service. The front steps are wobbly with no handrail. There is a big neon advertising sign above the porch. The owners only responded via email, ..."

Reviewed on Aug. 6, 2020

Jmeez Cabin Rentals
4 Bedroom Home Less Than a Mile to Hatfield/mccoy Trails
4 Bedroom Home Less Than a Mile to Hatfield/mccoy Trails
Williamson, WV
This family-friendly Williamson vacation home is located on a river, within 1 mi (2 km) of The Coal House and Williamson Memorial Fieldhouse. Tug Valley ARH ...
5/5Exceptional! (2 reviews)
Worth it!!
"Ashely was amazing to work with! The property was exactly as described. Very nice clean home! Perfect location for accessing Hatfield McCoy trails! Highly recommend."

Reviewed on Mar. 29, 2021

4 Bedroom Home Less Than a Mile to Hatfield/mccoy Trails
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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