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06 May 2025
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Bluegrass Backroads Road Trip Itinerary

Bluegrass Backroads Adventure Overview

Embark on an enchanting journey through the heart of Kentucky with the Bluegrass Backroads Adventure. This itinerary takes you through a captivating blend of vibrant city life, rich cultural heritage, and breathtaking natural beauty.

Start your exploration in Lexington, the renowned Horse Capital of the World. Discover the charm of this vibrant city as you explore its historic sites, beautiful horse farms, and a lively downtown area filled with exceptional dining and cultural experiences.

Next, delve into the rich heritage of Kentucky's bourbon at a Bourbon Distillery Tour. Witness the artistry and tradition behind this iconic spirit through engaging tours and tastings at renowned distilleries along the Kentucky Bourbon Trail, gaining an insider’s view of the distillation process.

Continue to the historic Keeneland Race Course, where you can experience the elegance and prestige of world-class horse racing in a picturesque setting. Keeneland is a true embodiment of Kentucky’s equestrian legacy, known for its rich traditions and thrilling races.

From there, immerse yourself in the simplicity and craftsmanship of the Shaker Village of Pleasant Hill. This historically preserved village offers a unique glimpse into Shaker life with its beautifully restored buildings, informative exhibits, and tranquil landscapes.

Finally, embrace the natural beauty of Red River Gorge, a paradise for outdoor enthusiasts. With its magnificent rock formations and extensive network of hiking trails, it’s a perfect spot for hiking, rock climbing, and enjoying the serene beauty of nature.

This eclectic itinerary promises a delightful mix of culture, history, and nature, making the Bluegrass Backroads Adventure a truly unforgettable experience.


Recommended Activities

  • Known as the Horse Capital of the World, Lexington offers a vibrant mix of historic sites, beautiful horse farms, and a lively downtown scene with great food and culture.
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    Bourbon Distillery Tour

    Experience the heritage and craftsmanship of Kentucky bourbon firsthand with tours and tastings at renowned distilleries along the Kentucky Bourbon Trail, learning about the distillation process.
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    Keeneland Race Course

    Keeneland is one of the most prestigious racecourses in the nation, known for its picturesque setting and hosting world-class horse racing events and sales.
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    Shaker Village of Pleasant Hill

    This beautifully preserved village offers a glimpse into the Shaker way of life, featuring historic buildings, engaging exhibits, and scenic landscapes that celebrate simplicity and craftsmanship.
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    Red River Gorge

    A natural wonder in Kentucky, Red River Gorge boasts stunning rock formations, extensive hiking trails, and is a popular destination for rock climbing and outdoor enthusiasts.
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Restaurants

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    The Grey Goose

    4.4
    $$$$

    The Grey Goose

    A hidden gem in Lexington known for its cozy atmosphere and delicious wood-fired pizzas, offering a unique twist on casual dining.
    4.4
    $$$$
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    Wallace Station Deli & Bakery

    4.6
    $$$$

    Wallace Station Deli & Bakery

    Nestled in horse country, this charming eatery is famous for its hearty sandwiches and homemade pastries, perfect for a countryside stop.
    4.6
    $$$$
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    Shaker Village Dining

    4.5

    Shaker Village Dining

    Experience traditional Shaker hospitality with farm-to-table dishes inspired by Shaker recipes, all set in a beautifully preserved historic village.
    4.5
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    Miguel's Pizza

    4.5
    $$$$

    Miguel's Pizza

    Located near Red River Gorge, this quirky pizza spot is a favorite among rock climbers and hikers, offering a relaxed vibe and tasty pizzas.
    4.5
    $$$$
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    Alchemy Restaurant & Bar

    Alchemy Restaurant & Bar

    An innovative dining experience inside the historic Dudley’s on Short, offering creative cocktails and a unique take on Southern cuisine.
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Stay Recommendations

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    The Inn at Shaker Village

    4.7

    The Inn at Shaker Village

    Experience a historical stay at this beautifully restored inn within the Shaker Village, offering cozy accommodations with a rich cultural backdrop.
    4.7
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    The 21c Museum Hotel Lexington

    The 21c Museum Hotel Lexington

    This boutique hotel combines contemporary art with luxurious accommodations, providing a unique cultural experience right in the heart of Lexington.
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    The Boone Tavern Hotel

    8.8

    The Boone Tavern Hotel

    Set in a historic building, this charming hotel offers Southern hospitality and is known for its rich history and classic Southern cuisine.
    8.8
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    Natural Bridge State Resort Park

    4.8

    Natural Bridge State Resort Park

    Stay amidst nature in this lodge offering breathtaking views, modern comforts, and easy access to the stunning Natural Bridge and Red River Gorge.
    4.8
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    The Kentucky Castle

    4.5

    The Kentucky Castle

    For a truly unique experience, stay at this luxurious castle, offering regal accommodations, farm-to-table dining, and a range of wellness activities.
    4.5
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Local Events & Happenings

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    Lexington SC vs. Oakland Roots SC

    Lexington SC vs. Oakland Roots SC

    The event will take place at Lexington Sporting Club Stadium in Lexington.
    Map IconLexington Sporting Club Stadium in Lexington (6.3 mi)
    Calendar Icon23 Aug 2025
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    Lexington SC vs. North Carolina FC

    Lexington SC vs. North Carolina FC

    The event will take place at Lexington Sporting Club Stadium in Lexington.
    Map IconLexington Sporting Club Stadium in Lexington (6.3 mi)
    Calendar Icon5 Sep 2025
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    Lexington SC vs. Orange County SC

    Lexington SC vs. Orange County SC

    The event will take place at Lexington Sporting Club Stadium in Lexington.
    Map IconLexington Sporting Club Stadium in Lexington (6.3 mi)
    Calendar Icon12 Sep 2025
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    Lexington SC vs. El Paso Locomotive FC

    Lexington SC vs. El Paso Locomotive FC

    The event will take place at Lexington Sporting Club Stadium in Lexington.
    Map IconLexington Sporting Club Stadium in Lexington (6.3 mi)
    Calendar Icon11 Oct 2025
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    Lexington SC vs. Sacramento Republic FC

    Lexington SC vs. Sacramento Republic FC

    The event will take place at Lexington Sporting Club Stadium in Lexington.
    Map IconLexington Sporting Club Stadium in Lexington (6.3 mi)
    Calendar Icon17 Oct 2025
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    CAIN

    CAIN

    The event will take place at EKU Center for the Arts in Richmond.
    Map IconEKU Center for the Arts in Richmond (10.64 mi)
    Calendar Icon16 Oct 2025
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    Maddox Batson

    Maddox Batson

    The event will take place at Manchester Music Hall in Lexington.
    Map IconManchester Music Hall in Lexington (12.8 mi)
    Calendar Icon30 Sep 2025
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