Prestonsburg

Travel Guide

Dewey Lake at Jenny Wiley State Resort Park

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 HK$925 per night from 19 Apr to 20 Apr
HK$925
HK$1,049 total
19 Apr - 20 Apr
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. ...
8.6/10 Excellent! (711 reviews)
The room was very clean and well-kept. Bathroom was likewise spotless. We enjoyed this stay.

Reviewed on 24 Mar 2026

Comfort Suites Prestonsburg West
Super 8 by Wyndham Prestonsburg

Super 8 by Wyndham Prestonsburg

2 out of 5
80 Shoppers Path Prestonsburg KY
The price is HK$592 per night from 20 Apr to 21 Apr
HK$592
HK$653 total
20 Apr - 21 Apr
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 (533 reviews)
I was woken up at little past midnight to being bitten by a bed bug. I informed the front desk immediately. The man at the counter was apologetic but could not help me in other way except to offer to place my clothes in a dryer. I left immediately!! Had to find another hotel in the middle of the ...

Reviewed on 22 Mar 2026

Super 8 by Wyndham Prestonsburg
Luxury Estate nestled atop stunning mountaintop golf course!

Luxury Estate nestled atop stunning mountaintop golf course!

Prestonsburg KY
Stay at this holiday home in Prestonsburg. Enjoy a garden, laundry facilities and patios. Popular attractions StoneCrest Golf Course and Jenny Wiley State Resort ...
9.8/10 Exceptional! (8 reviews)
Parking was easy. We had 6 cars. We had two dogs with us who did well and a neighborhood dog who came to visit and was a hit with the children.The entrance with the curved staircase was perfect for our balloon drop on New Year's Eve.If your visit is during the cold winter months, I would advise bringing ...

Reviewed on 5 Jan 2026

Luxury Estate nestled atop stunning mountaintop golf course!
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.
Luxury Estate nestled atop stunning mountaintop golf course!

Luxury Estate nestled atop stunning mountaintop golf course!

Prestonsburg KY
Stay at this holiday home in Prestonsburg. Enjoy a garden, laundry facilities and patios. Popular attractions StoneCrest Golf Course and Jenny Wiley State Resort ...
9.8/10 Exceptional! (8 reviews)
Parking was easy. We had 6 cars. We had two dogs with us who did well and a neighborhood dog who came to visit and was a hit with the children.The entrance with the curved staircase was perfect for our balloon drop on New Year's Eve.If your visit is during the cold winter months, I would advise bringing ...

Reviewed on 5 Jan 2026

Luxury Estate nestled atop stunning mountaintop golf course!
Cozy Home in Heart of Prestonsburg

Cozy Home in Heart of Prestonsburg

Prestonsburg KY
Stay at this holiday home in Prestonsburg. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Archer Park and Samuel May House are located ...
9.8/10 Exceptional! (10 reviews)
Everything was great! Easy check-in/checkout process and the host was very responsive to questions ahead of time.

Reviewed on 3 Mar 2026

Cozy Home in Heart of Prestonsburg
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 laundry facilities and air conditioning. Popular attractions Mountain Arts Center and Archer Park are located ...
2/10 (1 review)
The place does not exist. Could not find it. Called the host. Host had phone on not accepting calls. I was in the area for my mom's funeral. Had to scramble to find another place to stay.

Reviewed on 22 Jul 2024

New to the area? Stop by and see the most recent bachelor pad on the scene
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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