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7 Days of Hiking and History in Eastern Kentucky

7 Days of Hiking and History in Eastern Kentucky Itinerary

Last updated: 2024 Jun 14

Arrival and Relaxation in Pikeville

Morning
Arrive in Pikeville and check into your accommodation. Start your day with a hearty breakfast at Cloud 9 Cafe. This cozy spot is known for its delicious breakfast options and friendly atmosphere, perfect for fueling up before a day of exploration.
Afternoon
Spend the afternoon exploring the Pikeville Cut-Through Project. This engineering marvel is one of the largest earth-moving projects in the western hemisphere. Take a leisurely walk around the area and learn about its history through informative plaques.
Evening
For dinner, head to The Blue Raven. This highly-rated restaurant offers a variety of dishes made with locally-sourced ingredients. Enjoy a relaxing evening meal as you settle into your first day in Eastern Kentucky.
Bedtime
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Hiking and History in Prestonsburg

Morning
Start your day with breakfast at Billy Ray's Restaurant, known for its classic American breakfast options. Afterward, head to Jenny Wiley State Resort Park for some hiking. The park offers several trails that vary in difficulty, providing beautiful views of Dewey Lake and the surrounding forest.
Afternoon
After a morning of hiking, enjoy lunch at Pig in a Poke, famous for its barbecue dishes. In the afternoon, visit the Mountain Arts Center to learn about the region's rich musical heritage and perhaps catch a live bluegrass performance if available.
Evening
Dine at El Azul Grande Mexican Restaurant for some delicious Mexican cuisine. After dinner, take a relaxing stroll around downtown Prestonsburg or return to Jenny Wiley State Resort Park for some evening relaxation by the lake.
Bedtime
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Bourbon Tasting and Scenic Views in Hazard

Morning
Begin your day with breakfast at Giovanni's Pizza, which also serves excellent morning pastries and coffee. Then drive to Hazard to visit one of its renowned bourbon distilleries for a tasting tour.
Afternoon
For lunch, stop by Prime 606 Steakhouse to enjoy some hearty American fare. Spend your afternoon exploring Buckhorn Lake State Resort Park where you can hike or simply relax by the water while taking in scenic views.
Evening
Have dinner at Peking Chinese Buffet which offers an extensive selection of Chinese dishes. End your evening with a quiet night back at your accommodation or take an evening walk around Hazard.
Bedtime
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Historical Exploration in Ashland

Morning
Kick off your morning with breakfast at Subway before heading out to explore Ashland's historical sites such as the Paramount Arts Center and Highlands Museum & Discovery Center.
Afternoon
Enjoy lunch at Billy Ray's Restaurant, offering classic American dishes that are sure to satisfy any appetite. Spend your afternoon visiting Central Park or taking part in any local historical tours available.
Evening
For dinner, dine at Cloud 9 Cafe once more if you're back early enough; otherwise opt for another local favorite like Fat Patty’s (not on wishlist but highly recommended). Conclude your evening with some relaxation time back at your hotel.
Bedtime
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Natural Wonders and Local Flavors

Morning
Start your day with breakfast at Cloud 9 Cafe before heading to Cave Run Lake. Spend the morning hiking one of the many trails around the lake, taking in the beautiful natural scenery.
Afternoon
For lunch, visit Giovanni's Pizza for a delicious meal. Afterward, explore the Daniel Boone National Forest, where you can enjoy more hiking or simply relax and take in the serene environment.
Evening
Dine at Prime 606 Steakhouse for a hearty dinner. End your evening with a leisurely walk around Morehead or relax back at your accommodation.
Bedtime
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Cultural Immersion and Outdoor Fun

Morning
Billy Ray's Restaurant is a great spot for breakfast to start your day. Afterward, visit Berea College and explore its beautiful campus and artisan shops.
Afternoon
Pig in a Poke is perfect for lunch with its renowned barbecue dishes. Spend your afternoon hiking in the Berea Pinnacles, offering stunning views of the surrounding area.
Evening
El Azul Grande Mexican Restaurant will provide a delightful dinner experience. Conclude your day by attending a local bluegrass music event if available or relaxing back at your hotel.
Bedtime
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Final Day of Relaxation and Reflection

Morning
Begin with breakfast at The Blue Raven. Take some time to reflect on your trip while enjoying their excellent menu options.
Afternoon
Have lunch at Peking Chinese Buffet, offering an extensive selection of dishes. Spend your afternoon visiting any remaining sites you may have missed or simply relaxing before departure.
Evening
For dinner, choose El Azul Grande Mexican Restaurant. Conclude your trip with a final stroll around town or relax back at your accommodation before preparing for departure.
Bedtime
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