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
Fully refundable
The price is S$171 per night from 19 Apr to 20 Apr
S$171
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 S$106 per night from 5 Apr to 6 Apr
S$106
5 Apr - 6 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
Quality Inn & Suites Prestonsburg Next to Mountain Arts Center

Quality Inn & Suites Prestonsburg Next to Mountain Arts Center

2 out of 5
85 Hal Rogers Drive Prestonsburg KY
Stay at this hotel in Prestonsburg. Enjoy free parking, a fitness centre and laundry facilities. Popular attractions Mountain Arts Center and Archer Park are ...
Quality Inn & Suites Prestonsburg Next to Mountain Arts Center
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.
Near Scenic Parks: Convenient Home in Prestonsburg

Near Scenic Parks: Convenient Home in Prestonsburg

3 out of 5
Prestonsburg KY
Stay at this cottage in Prestonsburg. Enjoy a marina and air conditioning. Popular attractions Archer Park and Samuel May House are located nearby.
Near Scenic Parks: Convenient Home in Prestonsburg
Half-mi to Dawkins Rail Trail: Family Home w/ Yard

Half-mi to Dawkins Rail Trail: Family Home w/ Yard

3 out of 5
Hagerhill KY
Stay at this business-friendly cottage in Hagerhill. Enjoy free parking, in-room fireplaces and air conditioning. Popular attractions Preston Park and Paintsville ...
8/10 Very Good! (1 review)
Really liked the old house feel but very noisy by road

Reviewed on 13 Aug, 2023

Half-mi to Dawkins Rail Trail: Family Home w/ Yard
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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