☀️ 7-Night Itinerary 2 at Backroads & Barrels

Before You Arrive

Backroads & Barrels is located in a peaceful rural setting. Many groups find it helpful to bring their favorite groceries, snacks, breakfast items, beverages, and anything they'd like for a group meal. With two fully equipped kitchens, plenty of dining space, and outdoor gathering areas, it's easy to enjoy meals together without having to leave the property.

Day 1: Arrive, Stock Up & Settle In

Arrive at Backroads & Barrels and get settled.

Before arriving, or shortly after check-in, stock up on:
• Breakfast items
• Snacks
• Bottled water
• Favorite drinks
• Coffee
• Charcuterie items
• Grill-friendly dinners
• Anything you want for nights in

Backroads & Barrels is in a peaceful rural setting, and having food and drinks on hand makes the week much easier.

Dinner can be casual tonight. Pick up food nearby or make something easy at the house.

Evening:
• Drinks around the fire pit
• Hot tub and barrel sauna
• Texas Hold'em
• Pool and darts
• Home theater
• Plan your bourbon stops for the week

Day 2: Four Roses, Lawrenceburg & Wild Turkey

Start with breakfast at the house.

Head to Four Roses Distillery in Lawrenceburg for your first Bourbon Trail stop.

Enjoy:
• Distillery tour
• Tasting
• Visitor center
• Gift shop

Have lunch in Lawrenceburg.

In the afternoon, head to Wild Turkey Distillery. This gives you a second bourbon experience with a different feel and beautiful Kentucky River views.

Dinner in Lawrenceburg before heading back.

Evening at Backroads & Barrels:
• Barrel sauna
• Hot tub
• Bourbon tasting on the patio
• Golf simulator competition
• Texas Hold'em tournament

Day 3: Sleep In, Golf & Dinner Out

This is not a morning-to-night touring day.

Sleep in, enjoy coffee, and make breakfast at the house.

Late morning or early afternoon, golfers can head to Juniper Hill Golf Course or The Woodford Club.

Non-golfers can relax at the house, visit Tastefully Delicious, or enjoy a slow afternoon in Harrodsburg.

Dinner:
Choose Copper and Oak for craft cocktails and dinner, or The Still Restaurant & Cocktail Bar in Danville for a more elevated evening out.

After dinner, come back to the house for:
• Fire pit conversations
• Hot tub
• Theater room
• Late-night cards

Day 4: Woodford Reserve & Wildside Winery

Start with a relaxed breakfast at the house.

Head toward Versailles for Woodford Reserve Distillery. The setting, history, and horse-country scenery make this one of the standout bourbon experiences in the area.

After your tour and tasting, have lunch nearby or in Versailles.

In the afternoon, change the pace with Wildside Winery.

Take your time with:
• Wine tasting
• Vineyard views
• Outdoor seating
• Live music or events, when available

Head back to Backroads & Barrels before dinner.

Tonight is a perfect night in.

Dinner ideas:
• Grill steaks on the Traeger
• Build a bourbon-country charcuterie board
• Cook together using both kitchens
• Pick up food on the way back and keep it easy

Evening:
• Golf simulator
• Pool
• Darts
• Hot tub
• Barrel sauna

Day 5: Midway, Horse Country & No Rush

This is your slower Kentucky day.

Sleep in and have breakfast at the house.

Head to Midway late morning.

Spend time:
• Browsing local shops
• Visiting galleries
• Walking through the historic railroad town
• Stopping for coffee or a drink
• Enjoying the slower pace of horse country

Have lunch at The Blackbird Cafe.

After lunch, take a scenic route through horse country on the way back, or return to the house and enjoy the property.

Tonight is intentionally unscheduled.

Stay in and enjoy:
• Fire pit
• Texas Hold'em
• Home theater
• Golf simulator
• Sauna and hot tub

This is a good night for the group to split up naturally. Some people may want games. Some may want the hot tub. Some may want a movie. That is exactly why the house works so well for groups.

Day 6: Jeptha Creed or Talon Winery

Today gives the group a different direction.

Choose one main outing.

Option 1: Jeptha Creed Distillery

Head to Shelbyville for a family-owned craft distillery experience. Jeptha Creed is known for its grain-to-glass approach and Bloody Butcher corn.

Have lunch in Shelbyville or nearby.

Option 2: Talon Winery

Head toward Lexington for a relaxed winery experience with scenic views and tastings.

After your main stop, add one of these if the group wants more:
• Legacy Trail
• Mary Todd Lincoln House
• Downtown Lexington
• Coles 735 Main for dinner
• Merrick Inn for a special night out

Return to Backroads & Barrels for a quieter evening.

Day 7: Pick Your Perfect Final Day

The last full day should not feel packed.

Choose the version that fits your group.

Option 1: Lake & Outdoors

Spend time at Cummins Ferry or Cane Run Marina for kayaking, fishing, boating, walking trails, and water views.

Option 2: Golf & Dinner

Play Peninsula Golf Resort or Juniper Hill, then enjoy dinner at Serafini, Limewater, or The Woodford Club.

Option 3: Bourbon Encore

Revisit a favorite distillery, stop somewhere you missed, or pick up bottles to take home.

Option 4: Stay at Backroads & Barrels

Make the property the plan.

Suggested final-night lineup:
• Group dinner on the Traeger
• Bourbon tasting flight
• Golf simulator championship
• Texas Hold'em final table
• Hot tub
• Barrel sauna
• Fire pit under the stars

This is the night to slow down and enjoy the reason you booked a house instead of hotel rooms.

Day 8: Brunch & Departure

Enjoy one last slow morning.

Make coffee, finish leftovers, and take in the quiet setting before checkout.

If your route allows, stop for brunch or a final Kentucky treat on the way home.

Head Home

Leave refreshed, reconnected, and already talking about the next trip.