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PrestonsburgUnited States of America

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.

Top Hotels in Prestonsburg

Comfort Suites Prestonsburg West
Comfort Suites Prestonsburg West
2.5 out of 5
51 Hal Rogers Dr, Prestonsburg, KY
The price is CA $105 per night from Dec 20 to Dec 21

Located in the heart of Prestonsburg, this hotel is within 1 mile (2 km) of Mountain Arts Center and Middle Creek National Battlefield. Archer Park and Samuel ...

4.3/5Excellent! (279 reviews)

"Pool was great temperature. Couldn’t get on computer in lobby"…"

Reviewed on Sep. 28, 2020

Comfort Suites Prestonsburg West
Hilton Garden Inn Pikeville
Hilton Garden Inn Pikeville
3 out of 5
849 Hambley Blvd, Pikeville, KY
Free cancellationReserve now, pay when you stay
The price is CA $182 per night from Nov 25 to Nov 26

Located in the heart of Pikeville, this hotel is within a 10-minute walk of University of Pikeville and Eastern Kentucky Exposition Center. Pikeville Family ...

4.2/5Very Good! (57 reviews)
Pikeville Rockstar Hotel

"Great location, clean, modern with a classic twist. Service great, free structure parking, but food service could use some work (not that great due to COVID)."…"

Reviewed on Aug. 25, 2020

Hilton Garden Inn Pikeville
Jenny Wiley State Resort Park
Jenny Wiley State Resort Park
3 out of 5
75 Theatre Ct, Prestonsburg, KY
The price is CA $94 per night from Dec 1 to Dec 2

Situated in Prestonsburg, this hotel is 0.1 mi (0.1 km) from Jenny Wiley State Resort Park and within 6 miles (10 km) of StoneCrest Golf Course and Archer Park. ...

4.2/5Excellent! (167 reviews)

"Liked everything but the parking places for fishing was a bit rough"…"

Reviewed on Sep. 17, 2020

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.

Vacation Rentals in Prestonsburg

Private & Secluded Yatesville Lake Cabin Rental, Lakeview, Wifi, Kayaks, Arcade!
Private & Secluded Yatesville Lake Cabin Rental, Lakeview, Wifi, Kayaks, Arcade!
261 Left Fork Little Blaine Creek Rd, Louisa, KY

Situated in Louisa, this romantic cabin is 1 mi (1.6 km) from Yatesville Lake State Park and 1.3 mi (2.1 km) from Eagle Ridge Golf Course. The Paveillon and ...

4.9/5Exceptional! (85 reviews)
Loved it!

"Great!"…"

Reviewed on Nov. 19, 2020

Private & Secluded Yatesville Lake Cabin Rental, Lakeview, Wifi, Kayaks, Arcade!
Jmeez Cabin Rentals
Jmeez Cabin Rentals
44 oakwood height, Williamson, WV
The price is CA $163 per night from Nov 25 to Nov 26

Situated in Williamson, this cabin is within 1 mile (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
Jmeez Cabin Rentals
Jmeez Cabin Rentals
40 Oakwood height, Williamson, WV

Situated in Williamson, this cabin is within 1 mile (2 km) of The Coal House and Williamson Memorial Fieldhouse. Tug Valley ARH Regional Medical Center is 1.8 ...

5/5Exceptional! (1 review)
,

","…"

Reviewed on Sep. 24, 2020

Jmeez Cabin Rentals
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.

Cities near Prestonsburg