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 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.

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 RM513 per night from 25 Nov to 26 Nov
RM513
RM582 total
25 Nov - 26 Nov
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! (352 reviews)
Jamie at the front desk is awesome as always very professional and very knowledgeable about the town

Reviewed on 13 Nov 2025

Quality Inn & Suites Prestonsburg next to Mountain Arts Center
Comfort Suites Prestonsburg West

Comfort Suites Prestonsburg West

2.5 out of 5
51 Hal Rogers Dr Prestonsburg KY
The price is RM422 per night from 18 Dec to 19 Dec
RM422
RM479 total
18 Dec - 19 Dec
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! (682 reviews)
Rooms were nice ice machine on the floor was broken

Reviewed on 11 Nov 2025

Comfort Suites Prestonsburg West
Super 8 by Wyndham Prestonsburg

Super 8 by Wyndham Prestonsburg

2 out of 5
80 Shoppers Path Prestonsburg KY
Fully refundableReserve now, pay when you stay
The price is RM269 per night from 14 Dec to 15 Dec
RM269
RM297 total
14 Dec - 15 Dec
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 (510 reviews)
friendly fast front desk personnel.

Reviewed on 12 Nov 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.
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 Samuel May House and Archer Park 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 family-friendly cottage in Hagerhill. Enjoy free parking, patios and in-room fireplaces. Popular attractions Preston Park and Paintsville Golf Course ...
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.

Popular places to visit