Tour Guide

Jenny Wiley State Resort Park

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419 Lodge Road

Start your journey at Jenny Wiley State Resort Park, where you can experience the secluded Appalachian mountain beauty up close and personal. Jenny Wiley is home to over 60 miles of hiking trails for all experience levels. Trails wind through the large mountains, offering a variety of mountain top peak or valley views. For an even more interactive experience, book your pontoon boat tour of Dewey Lake. Begin your adventure early to catch the sun glistening through the trees as it rises. Don't forget to ask about Jenny Wiley Theatre, one of the country's longest running professional outdoor theatres, located within the State Park.


RIDE FROM...
Jenny Wiley State Resort Park to City Perk Coffeehouse
(4 miles, about 30 minutes)

1. Ride west on Theatre Court toward Jenny Wiley Drive
2. Turn left onto Jenny Wiley Drive
3. Continue onto KY-302 S/Water Gap Road
4. Turn right onto S Lake Drive
5. Turn right onto Hyden Lane
6. Turn left onto E Graham Street
7. Turn right onto Lafferty Lane
8. City Perk Coffeehouse will be on your right

City Perk Coffeehouse

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225 E Graham Street

Enjoy a hot (or iced) cup of coffee and delicious baked treats at City Perk for breakfast. Every cup of coffee is made with love and locally roasted beans that are ground fresh daily. They've also got a fresh squeezed rose lavender lemonade, a fully stocked bakery case, and art gallery that you won't want to miss!


RIDE FROM...
City Perk Coffeehouse to Archer Park
(1 mile, about 12 minutes)

1. Ride southeast on Lafferty Lane toward E Graham Street
2. Turn right onto E Graham Street
3. Turn right onto S Arnold Avenue
4. Turn left onto KY-114 W (use caution and ride on the shoulder of the road)
5. Turn right onto Main Street
6. Turn left onto Archer Park Road
7. Turn right onto Memorial Drive and arrive at Archer Park

Archer Park

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66 Archer Park Road

Stop for a stroll around Archer Park. Archer Park is a green space set against rolling hills. The centerpiece of the park is a military memorial with a beautiful fountain surrounded by American flags. During the holiday season, this park is transformed into a winter wonderland complete with a skating rink and spectacular display of Christmas lights. Take a breather here and enjoy the fresh mountain air. For those looking for more adventure, access to the rails-to-trails path is available here, too.


RIDE FROM...
Archer Park to Mountain Arts Center
(3 miles, about 25 minutes)

1. Ride southeast on Memorial Drive toward Archer Park Road
2. Turn left onto Archer Park Road
3. Turn left onto Main Street
4. Turn left onto Harkins Avenue
5. Turn left onto Duncan Street/KY-2555/Old 114
6. Turn left onto KY-114 E (use caution and ride on the shoulder of the road)
7. Turn left onto Hal Rogers Drive to arrive at Mountain Arts Center

Mountain Arts Center

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50 Hal Rogers Drive

Just a stone's throw from the Country Music Highway in Prestonsburg you'll find the Mountain Arts Center or "MAC". The MAC is a state-of-the-art music venue complete with a recording studio, art gallery, practice space for musicians, and 1100 seat concert venue. Catch a number of the country's top performing artists in concert or the famous Kentucky Opry every summer and winter. If you're ready to hit the stage, yourself, join Front Porch Pickin' live on stage every summer. The MAC is also home to the Ranier Racing Museum, which will give you the need for speed!


RIDE FROM...
Mountain Arts Center to Rainbow Arch Bridge
(2 miles, about 23 minutes)

1. Ride south on Hal Rogers Dr toward KY-114 W
2. Turn left onto KY-114 E (use caution and ride on the shoulder of the road)
3. Turn left onto N Arnold Avenue
4. Rainbow Arch Bridge will be on the left

Rainbow Arch Bridge

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The West Prestonsburg Rainbow Arch Bridge is an iconic local structure that dates back to 1925. The concrete bridge received national historic landmark status in 1989. The bridge gets its nickname from its rainbow-like arch shape which gracefully rises over the waters of Levisa Fork River.


RIDE FROM...
Rainbow Arch Bridge to Lunch Like a Local

1. Ride Northwest on N Arnold Avenue toward Patton Street
2. Turn right onto Patton Street
3. Turn left onto N Lake Drive

To go to Pig in a Poke...

4. Turn left onto University Drive
5. Pig in a Poke will be on the left

To go to Lizzie B's...
This extension is recommended for intermediate and advanced cyclists only.

4. Continue on Lake Drive toward Jackson Street
5. Continue to follow KY-3 N/KY-321 N as it curves to the right (The shoulder on CR321 narrows and the road has a blind curve for approximately 0.5 miles. Use extreme caution while cycling this segment.)
6. Lizzie B's Cafe Bakery will be on the right

Pig in a Poke

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341 University Drive

It's a good thing you worked up an appetite with all that pedaling! Dig into real pit smoked BBQ at Pig in a Poke. And don't forget the sides. From friend pickles to baked beans, you're in for a real southern treat!


Lizzie B's

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2010 KY-321

If you prefer Hawaiian flare, chill out at Lizzie's. The surf style shop will make you think you're surrounded by beach waves instead of mountain peaks. Enjoy all the flavors of the katsu chicken or fill up on vegetables with one of the famous freshly baked sandwiches.


RIDE FROM...
Lunch to Mayhouse Living History Museum

If riding from Pig in a Poke...

1. Ride north on University Drive
2. Turn right onto Porter Lane
3. Mayhouse Living History Museum will be on the right

If riding from Lizzie B's...

1. Ride south on KY-3 N/KY-321 N
2. Turn right on Porter Lane
3. Mayhouse Living History Museum will be on the left

Mayhouse Living History Museum

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220 Porter Lane

This Federal-style home was constructed in 1816 and is the oldest home in Prestonsburg. Confederate Colonel Andrew Jackson May lived in the house during his childhood. During the Civil War, the house functioned as a recruiting station for the Confederate forces. Today the house is furnished with items from the time period in which it was built to give you a sense of life in the mid-1800s. Music and seamstress lovers will fall in love with the many antique organs and sewing machines.


RIDE FROM...
Mayhouse Living History Museum to East Kentucky Science Center & Planetarium
(0.5 miles, about 2 minutes)

1. Ride northwest on Porter Lane toward Green Acres Drive
2. Turn right onto University Drive
3. Turn right onto Bert Combs Drive and arrive at the East Kentucky Science Center & Planetarium

East Kentucky Science Center & Planetarium

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1 Bert Combs Drive

The East Kentucky Science Center and Planetarium is is one of the most technologically advanced in the nation. A night sky full of stars is projected by a GOTO Chronos Spaceflight Simulator onto the planetarium's 40-foot dome, recreating an accurate and spectacular field of stars. Out of this world laser shows are paired with classic Pink Floyd hits and genres that are sure to wow. This must-see stop is educational and entertaining. Showtimes are 2pm and 3:15pm, with a 12:30pm matinee added every Saturday.


RIDE FROM...
East Kentucky Science Center & Planetarium to Dairy Cheer
(1 mile, about 8 minutes)

1. Ride west on Bert Combs Drive toward University Drive
2. Turn left onto University Drive
3. Turn left onto Porter Lane
4. Turn left onto KY-3 N/KY-321 N
5. Dairy Cheer will be on the right

Dairy Cheer

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1384 N Lake Drive

After all that star gazing, it's time for a sweet treat. Dairy Cheer has been a Prestonsburg staple since 1984. Look for the classic Dairy Cheer sign to find your way to a delicious meal. The signature "Smashburger" gets its name from a technique discovered by Dairy Cheer owner Bill Culvertson when he found that smashing burgers on the grill with a bean can enhance the flavor. The endless icecream flavors is what really keeps people coming back for more. Grab a famous Dairy Cheer swirl and feel like a kid all over again.


RIDE FROM...
Dairy Cheer to Downtown Shopping District
(1 mile, about 8 minutes)

1. Ride south on KY-3 S/KY-321 S toward Porter Lane
2. Continue onto N Lake Drive
3. Turn left onto E Court Street to arrive at the Downtown Shopping District

Downtown Shopping District

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Court Street

Hop off the bike and take a stroll through Prestonsburg's progressive downtown area. A mini-park and beautiful mural at Lake Drive and Court Street welcome you to the "The Star City's" quaint downtown. Court Street is lined with local shops, art spaces, and boutiques where you can browse the storefronts and shop for mementos from your journey.


From the Downtown Shopping District stroll south on E Court Street toward the river to Billy Ray's Restaurant or continue down Lake Drive to The Brickhouse.

Billy Ray's Restaurant

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101 N Front Street

If you're craving a hearty meal, then end your day at Billy Ray's Restaurant. They've got daily specials and a full menu of comfort food favorites, from country fried steak to chili to their signature "Poolroom" burger. Enjoy the southern hospitality and charm of this local eatery whose decor gives off classic "Cheers" vibes.


The Brickhouse

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358 S Central Avenue

End the evening with a locally brewed night cap and the best up-and-coming musical artists. Brickhouse hosts live local musicians every weekend and often throughout the week. Don't want to miss your favorite sports team in action? This is the perfect spot to catch a game and reflect on the day's adventure. And if a post-dinner slice of pizza is calling your name, it's only fair to answer. On a nice day, you can sit out on the wrap-around porch and dig into their menu of American fare. The unique pizzas include the "Kentucky Hot Brown Pizza" - a signature dish inspired by a regional favorite, the Hot Brown.


RIDE BACK TO...
Jenny Wiley State Resort Park
(4 miles, about 30 minutes)

1. Ride northeast on S Lake Dr toward S Central Avenue
2. Turn left onto KY-302 N/Water Gap Road
3. Make a slight right onto Jenny Wiley Drive
4. Turn right onto Theatre Court to arrive back at Jenny Wiley State Resort Park

Welcome to Prestonsburg!


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Prestonsburg was the first established town in Eastern Kentucky. A place enriched with arts, history, and adventure distilled from Appalachia. Known as The Star City of Eastern Kentucky, Prestonsburg is strategically located at the hub of 5 major highways (as represented by the five-pointed star). Those highways include US 23 North, US 23 South, KY Route 80, KY Route 3, and KY Route 114 (Mountain Parkway).

The star also represents the vast amount of entertainment in Prestonsburg. The Mountain Arts Center is a 1,050 seat theater that presents local talent, like the acclaimed Kentucky Opry, as well as national headliners. Jenny Wiley Theater, located within the renowned Jenny Wiley State Resort Park, has been providing "magic under the stars" for decades with its classic outdoor Broadway-style shows. StoneCrest Golf Course, which was built on a reclaimed mountain top, puts you as close to the stars as you can get. The newest addition to a galaxy of fun is the East Kentucky Science Center & Planetarium, the most technologically advanced center in the U.S., with its exhibits, laser shows, and 40-foot domed planetarium.

Prestonsburg, The Star City of Eastern Kentucky, is in the heart of Appalachia. Located on US 23, the County Music Highway and national scenic byway is home to many country music legends including Floyd Countian Dwight Yoakam born just miles from Prestonsburg. Prestonsburg offers live theatre, star performers, festivals, local dining, crafts, horse shows, boating, hiking, elk and nature watching adventures, golfing, historical sites, and other recreational activities. Browse our website, create your own itinerary, and make plans to visit with us for an unforgettable and enjoyable experience!

Safety Info

You should consult your physician before starting any exercise program. Bicycling is an activity with risk of personal injury. Prestonsburg Tourism Commission and its affiliates are not responsible in any capacity for harm or injury that may occur as a result of bicycling. You are solely responsible for your safety while biking.