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5 Days on the Kentucky Bourbon Trail (A Travel Guide)

Dog friendly Airbnb perfect for a 5 day trip on the Bourbon Trail.

Is the greatest place on earth the Bourbon Trail? If you love bourbon, you will definitely think so. There are over 95 distilleries in Kentucky to visit and experience. (With all your favorites!) You can follow the main bourbon trail or you can hop onto the craft bourbon trail. It is bourbon heaven. I had a wonderful 5 day trip on the Kentucky Bourbon Trail. This travel guide will help you build a full but relaxing 5 day trip on the Bourbon Trail in Kentucky. This travel guides includes the best places to stay on the Bourbon Trail, best things to do on the Bourbon Trail and best Bourbon distilleries to visit.

At Pragmatic Travelers, I only recommend what I have actually experienced, tasted and drank. I am affiliated with Booking.com. If you book the vacation rental below, I will earn a small commission with no additional expense to you.

Bardstown Bourbon Company is  one of the best distilleries to visit while on a 5 day trip to the Bourbon Trail.
Bardstown Bourbon Company a great distillery to visit on the Bourbon Trail.

Check out our favorite East Coast Road Trip stops for more travel inspiration!

Tips and Trick for the Bourbon Trail

  • Kentucky is BIG. The bourbon trail is spread out so make sure you have a car and are prepared to drive.
  • The bourbon trail is popular right now so if you have a particular distillery you want to visit make sure to book a tour in advance.
  • Check out the different types of experiences a distillery offers. Don’t pigeonhole yourself to just tours.
  • Many distilleries offer cocktails/tasting flights so if you don’t go on a tour you can still enjoy the bourbon.
  • Also drink cocktails because bourbon cocktails are the best.
Great place to stay on the Bourbon Trail. Dog Friendly Airbnb on Bourbon Trail.
Sunset at the horse farm. A wonderful dog friendly vacation rental on the Bourbon Trail.

Great Place to Stay on Bourbon Trail

I had a hard time finding a place to stay since the bourbon trail is so spread out. I ended up picking a vacation rental on Booking.com that I just really liked and was dog friendly. (We traveled with our senior doggo.) I just resigned myself to driving. This Airbnb was on a horse farm (see picture at top of page) and the horses came by to say hello each day. It was very clean and cozy with an enclosed yard. It was close to Wild Turkey and Four Roses. Highly Recommend. Link below.

Charming Guesthouse Getaway on 10-Acre Farm

Not feeling this Airbnb? Check out the hotels in Louisville or in Lexington. I haven’t stayed in one so don’t have one to recommend.

Four Roses Distillery one of the best distilleries on the Bourbon Trail.
Four Roses Distillery. A wonderful place to visit on the Bourbon Trail.

Best Distilleries on the Bourbon Trail.

  • Four Roses DistilleryThis was my favorite tour and experience. (I am biased as this is my favorite bourbon.) Wonderful tasting, gift shop and bar.
  • Bardstown Bourbon Company-This is a newer distillery full of high tech bells and whistles. The tour itself was excellent. Very informative. There is a restaurant and bar within the distillery. Highly Recommend.
  • Lux Row Distillery– Beautiful building with excellent cocktail bar. The cocktails in particular were delightful.
  • Wilderness Trail DistilleryIt was originally on the craft bourbon trail and has recently moved to the main trail. Cozy cocktail area with informative tour and tasting. Not my favorite bourbon but was fun to try.
  • Heaven Hill Distillery-It is massive and produces some truly excellent bourbon. Large cocktail bar as well.
Four Roses Tasting experience. An excellent thing to do on the Bourbon Trail.
Four Roses Tasting: Wonderful experience on the Bourbon Trail.

Great Restaurants on the Bourbon Trail

  • Mammy’s Kitchen and Bar, Bardstown-While not my favorite restaurant of the trip, the BBQ chicken sandwich and pimento cheese were very good. Nice patio area as well.
  • Mussels & Burger Bar, Louisville- Excellent mussels with really great bourbon cocktails. Close to the major attractions in Louisville.
  • Copper and Oak, Danville-The signature burger was absolutely delicious. The bourbon based cocktails like the Prohibition Old Fashioned were amazing. Highly recommend.
Louisville Slugger Museum is a great thing to do on the Bourbon Trail.
Louisville Slugger Museum is a great thing to do on the Bourbon Trail.

Best things to do on the Bourbon Trail

  • Louisville Slugger Museum and Factory, LouisvilleThis was one of my favorite experiences ever. You get to walk through and see how bats are made. THEN you can hold Babe Ruth’s bat. I am not kidding! Go there. Make sure to walk along the sidewalk near the museum. They installed over 60 bronze bats modeled after the same bats our favorite baseball giants used. (Such as Babe Ruth and Hank Aaron)
  • Justin’s House of Bourbon-Located in at a few different places in Kentucky. Nice place to go and sample different kinds of bourbon if you can’t get to all of the distilleries. Cocktails were fine not great.
  • Visit a distillery, duh. See above.
  • Visit a small Kentucky town. Here are my favorites:
    • Bardstown-lovely main street to walk around. Claims to be the main bourbon town.
    • Harrodsburg-Small but cute main street.
    • Danville-Adorable small town. Near Wilderness Trail Distillery.
Heaven Hill Distillery is one of the best distilleries on the Bourbon Trail.
Heaven Hill Distillery

Important Resource

Make sure to visit the main bourbon trail website. This will provide a plethora of information on different distilleries and where they are located. See link below.

Kentucky Bourbon Trail

Your Thoughts…

This was our favorite parts of time on the Kentucky Bourbon Trail. What did you enjoy visiting? What was your favorite distillerary? Leave a comment below!

Wilderness Trail Bourbon tour. A perfect thing to do on a 5 day trip to the Bourbon trail.
Wilderness Trail Rackhouse

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