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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.
    Open Google Maps Button
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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.
    Open Google Maps Button
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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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Hotels

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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

  • Event Icon

    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
    Picture for Lexington SC vs. Orange County SC
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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
    Picture for Lexington SC vs. El Paso Locomotive FC
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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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    2025 Football Season Ticket Deposit

    2025 Football Season Ticket Deposit

    The event will take place at Kroger Field in Lexington.
    Map IconKroger Field in Lexington (13.08 mi)
    Calendar Icon30 Nov 2025
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Travel Gems from Reddit

  • Reddit Icon

    Great west KY barbeque, it is different than any other flavor you will experience during your trip. If you are traveling a bit later in the year, expanding your range will cer...

    On a road trip across the southern states. Would like to know things to see and do around Kentucky.

    Great west KY barbeque, it is different than any other flavor you will experience during your trip. If you are traveling a bit later in the year, expanding your range will cer...

    /r/Kentucky
  • Reddit Icon

    183 votes, 62 comments. 169K subscribers in the Kentucky community. /r/Kentucky

    Backroads, everywhere, Kentucky

    183 votes, 62 comments. 169K subscribers in the Kentucky community. /r/Kentucky

    /r/Kentucky
  • Reddit Icon

    369 votes, 42 comments. 190K subscribers in the Miata community. A subreddit for all those who have owned, driven, raced, admired, or had anything

    The backroads of Kentucky are great.

    369 votes, 42 comments. 190K subscribers in the Miata community. A subreddit for all those who have owned, driven, raced, admired, or had anything

    /r/Miata
  • Reddit Icon

    My wife and I sidetracked through Owensboro KY to see the Bluegrass Hall of Fame . We loved it. There is a nice flow from the beginnings through the

    Bluegrass Hall of Fame is worth the trip.

    My wife and I sidetracked through Owensboro KY to see the Bluegrass Hall of Fame . We loved it. There is a nice flow from the beginnings through the

    /r/Bluegrass
  • Reddit Icon

    19 votes, 26 comments. Hello you MBs! My gf is taking me on a KY Trail Trip for my birthday this year (October) and I had some questions. First

    KY Bourbon Trail advice for a newbie

    19 votes, 26 comments. Hello you MBs! My gf is taking me on a KY Trail Trip for my birthday this year (October) and I had some questions. First

    /r/WhiskeyTribe
  • Reddit Icon

    10 votes, 19 comments. What are they best local restaurants along the Bourbon trail? Stay on the east side of Louisville, and have tours book at Four

    Restaurant along the bourbon trail

    10 votes, 19 comments. What are they best local restaurants along the Bourbon trail? Stay on the east side of Louisville, and have tours book at Four

    /r/Kentucky
  • Reddit Icon

    Hi all, Live in IL and hoping to plan a road trip down and around Kentucky. Prefer more scenic viewpoints to city stuff. Definitely want to check out

    Help planning a road trip

    Hi all, Live in IL and hoping to plan a road trip down and around Kentucky. Prefer more scenic viewpoints to city stuff. Definitely want to check out

    /r/Kentucky

Music for Your Journey

  • Music Icon

    Bill Monroe & His Blue Grass Boys - Blue Moon Of Kentucky

    Bill Monroe & His Blue Grass Boys - Blue Moon Of Kentucky

    A classic bluegrass tune that perfectly sets the mood for a road trip through Kentucky's beautiful landscapes.
    Listen on Spotify
    Picture for Bill Monroe & His Blue Grass Boys - Blue Moon Of Kentucky
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    John Denver - Take Me Home, Country Roads

    John Denver - Take Me Home, Country Roads

    An iconic song celebrating rural roads and nostalgic journeys, ideal for feeling connected to the surroundings.
    Listen on Spotify
    Picture for John Denver - Take Me Home, Country Roads
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    Elvis Presley - Kentucky Rain

    Elvis Presley - Kentucky Rain

    This evocative song captures the essence of traveling through Kentucky’s changing weather and lush scenery.
    Listen on Spotify
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    Darius Rucker - Wagon Wheel

    Darius Rucker - Wagon Wheel

    A modern classic that embodies the spirit of adventure on the open road, perfect for laid-back listening.
    Listen on Spotify
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    Acoustikats - My Old Kentucky Home

    Acoustikats - My Old Kentucky Home

    A nostalgic ballad that reflects on the picturesque beauty and heartfelt traditions of Kentucky.
    Listen on Spotify
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    The Osborne Brothers - Rocky Top

    The Osborne Brothers - Rocky Top

    An upbeat bluegrass favorite that celebrates the joys of rural life and the countryside’s simple pleasures.
    Listen on Spotify
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    James Taylor - Carolina in My Mind

    James Taylor - Carolina in My Mind

    Though not about Kentucky, this reflective tune’s mellow vibe complements the serene atmosphere of the journey.
    Listen on Spotify
    Picture for James Taylor - Carolina in My Mind
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    The Beatles - The Long And Winding Road - Remastered 2009

    The Beatles - The Long And Winding Road - Remastered 2009

    A somber yet hopeful song about travel and introspection, perfect for contemplative stretches of the drive.
    Listen on Spotify
    Picture for The Beatles - The Long And Winding Road - Remastered 2009
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    Hank Williams, Jr. - A Country Boy Can Survive

    Hank Williams, Jr. - A Country Boy Can Survive

    This song oozes country confidence and resilience, fitting for a trip embracing the rural spirit.
    Listen on Spotify
    Picture for Hank Williams, Jr. - A Country Boy Can Survive
  • Music Icon

    Dolly Parton - Jolene

    Dolly Parton - Jolene

    A compelling story-driven ballad with a strong country feel, adding depth and emotion to the playlist.
    Listen on Spotify
    Picture for Dolly Parton - Jolene