Summary:
Welcome to the Trailhouse, an elevated, bourbon-inspired speakeasy retreat. The Trailhouse puts your group right on Bardstown Road, in the heart of Louisville’s walkable Highlands neighborhood. Restaurants, cafes, bourbon bars, and activities are steps away, while this 2,500+ sq. ft. estate provides room for up to 16 guests to enjoy. Relax in the upscale sipping room and cocktail lounge, then unwind in the private courtyard with a hot tub, firepit, and grill.

The Space:
The Trailhouse's sipping room offers intimate lounge-style seating, while the fully-equipped gourmet kitchen and cocktail bar combine island seating and bistro tables for casual meals and drinks as a group. Rich colors, original stained glass, and warm fireplaces add to the home’s speakeasy feel. Seven private bedrooms across three levels offer plenty of room for families and groups, with 3.5 bathrooms and Smart TVs throughout the home for added comfort and convenience.

The private, enclosed courtyard creates a relaxing outdoor gathering space with a hot tub, firepit seating, and a grill for meals outside. Louisville-inspired murals add a distinctive local touch, while an upper deck provides another comfortable lounge area with exterior staircase access to the courtyard below.

Why Guests Love The Trailhouse ⭐
📍 Spacious and private with a secluded feel, but ideally located in the Highlands neighborhood close to all the action
🥃 Speakeasy-inspired sipping room with intimate lounge seating
♨️ Private courtyard hot tub for relaxing after exploring Bourbon Country
🔥 Outdoor firepit for gathering together
🍸 Wet bar and lower-level dining area with bistro and island seating
🛏️ Seven bedrooms accommodating up to 14 guests
🛁 Clawfoot soaking tub and 3.5 bathrooms
🌿 Private courtyard and upper deck with outdoor seating and grill

Ideal Location 📍
The Trailhouse is located directly on Bardstown Road in Louisville’s vibrant Highlands neighborhood, known for its walkable streets, independent restaurants, bourbon bars, coffee shops, and nightlife. Local favorites like Holy Grale, Gralehaus, and Jack Fry’s are just steps away, making it easy to explore the neighborhood on foot. Downtown Louisville, NuLu, and the city's famous Bourbon Trail attractions are also within easy reach.

Accommodations 🛏️
• Master bedroom: king bed and ensuite bathroom
• Second bedroom: king bed
• Third bedroom: king bed
• Fourth bedroom: queen bed and two single beds
• Fifth bedroom: queen bed and single bed
• Sixth bedroom: bunk bed, sofa bed and workspace
• Seventh bedroom: sleeping nook with sofa bed and smart TV
• Three full bathrooms and one half bathroom serve the home across each of its three levels

Kitchen & Dining 🍳
• Bourbon-inspired kitchen with rich finishes, vintage details, and speakeasy charm
• Spacious marble island with comfortable seating for cocktails and casual dining
• Intimate bistro seating reminiscent of a classic bourbon lounge
• Fully-equipped for preparing meals and entertaining
• Coffee bar station with Keurig and drip coffee options

Sipping Room & Entertainment 🥃
• Speakeasy-inspired sipping room with intimate lounge seating
• Vintage accents create an authentic bourbon lounge atmosphere
• Cozy fireplace for relaxing evenings at home
• Smart TVs throughout the home
• Board games for entertaining family and friends

Outdoor Living 🌿
• Private, enclosed courtyard with a hot tub for relaxing after a day exploring Louisville
• Firepit with comfortable seating for evenings outdoors
• Grill for casual cookouts and meals at home
• Upper deck with additional lounge seating overlooking the courtyard
• Louisville-inspired speakeasy murals add distinctive local character

Nearby Attractions 🏡
• Holy Grale & Bar Grale – 1 minute walk • craft beer and seasonal dining
• Gralehaus – 2 minute walk • popular neighborhood café serving coffee and brunch
• Jack Fry’s – 2 minute walk • historic Louisville restaurant known for its upscale American cuisine
• Quills Coffee – 4 minute walk • local coffee shop serving espresso drinks and fresh pastries
• Neat Bourbon Bar & Bottle Shop – 5 minute walk • neighborhood bourbon bar featuring rare pours and classic cocktails
• Awry Brewing – 10 minute walk • local craft brewery with a casual atmosphere and food menu
• NuLu – 8 minute drive • vibrant arts and shopping district with boutiques, galleries, and restaurants
• Angel’s Envy Distillery – 8 minute drive • guided bourbon distillery tours and tastings
• Downtown Louisville & Whiskey Row – 10 minute drive • historic bourbon destinations, restaurants, and waterfront attractions
• Churchill Downs & Kentucky Derby Museum – 15 minute drive • iconic racetrack, racing history, and guided tours

Guest Access:
Guests have private access to the entire home, including all bedrooms, the sipping room, kitchen, laundry area, upper deck, and courtyard with the hot tub, firepit, and grill. Free street parking is available, and guests are welcome to enjoy all the home's amenities during their stay.

The Neighborhood:
You'll be staying in the Highlands, one of Louisville's most walkable and coveted neighborhoods with dozens of activities, restaurants, bars, and places to explore.

Getting Around:
Many neighborhood restaurants, coffee shops, bars, and shops are within walking distance, making it easy to enjoy the Highlands without using a car for every outing. Rideshares like Uber and Lyft are a convenient option for Downtown Louisville, NuLu, distillery visits, and Churchill Downs. A vehicle is useful for Bourbon Trail destinations beyond the city. Free street parking is available.

Other Things to Note:
The Trailhouse is a truly special Louisville retreat, and we ask guests to treat the property, surrounding grounds, and amenities with the care and respect they would their own.

Smoking, parties, and events are strictly prohibited and subject to fines.

Pets are not permitted.

Interaction with Guests:
We give our guests space to settle in and enjoy their stay, while remaining available if you need us. Please reach out with any questions before or during your visit.