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 £92 per night from 22 Aug to 23 Aug
£92
22 Aug - 23 Aug
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! (649 reviews)
"The beds were very comfortable and the couch was too. Breakfast was fabulous! Would definitely stay there again."

Reviewed on 13 Aug 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 £78 per night from 8 Sept to 9 Sept
£78
8 Sept - 9 Sept
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 ...
8/10 Very Good! (321 reviews)
"Well lite ,, plenty of parking ,"

Reviewed on 15 Aug 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 £55 per night from 2 Sept to 3 Sept
£55
2 Sept - 3 Sept
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 (495 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.
Luxury Estate nestled atop stunning mountaintop golf course!

Luxury Estate nestled atop stunning mountaintop golf course!

2 out of 5
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 ...
10/10 Exceptional! (5 reviews)
Jewel of a place
"This estate was a perfect family gathering to celebrate a milestone birthday. The host gave important information in a timely manner and the housekeeper answered questions quickly and precisely. The place is kept up and nestled in a beautiful location. Three of the family members played golf one ..."

Reviewed on 27 Jun 2025

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 ...
10/10 Exceptional! (7 reviews)
Short Stay in Prestonsburg
"We were in town for my Grannys funeral. She grew up in this area. This house was perfect. It was walking distance to downtown. Plenty of room. Nice sized kitchen. Very clean with the peefect backyard for visiting. Will stay here again when we are back in town."

Reviewed on 13 Jul 2025

Cozy Home in Heart of Prestonsburg
Near Scenic Parks: Convenient Home in Prestonsburg

Near Scenic Parks: Convenient Home in Prestonsburg

Prestonsburg, KY
Stay at this holiday home in Prestonsburg. Enjoy laundry facilities, cable/satellite TV service and an in-room coffee maker. Popular attractions Samuel May House ...
10/10 Exceptional! (2 reviews)
Beautiful place
"The inside was decorated beautifully, Loved the garage And( even though we didnt use) washer and dryer."

Reviewed on 4 May 2025

Near Scenic Parks: Convenient Home in 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.

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