Road Trips, United States

Hooch, Horses & Hiking: Four Days & A 40th Birthday in Kentucky

Stopping along the Auxier Trail in Red River Gorge

What do you get for a whisky-loving wanderluster that’s nearing the big 4-0? A weekend away, family style, with a dabbling of distilleries and a whole lot of hiking (because that’s also one of his favorite things).

In March 2022, we escaped on a three-night, four-day weekend that was planned as a surprise for the birthday fella, with hopes to blend a few of his hobbies, pack in some quality family time and also explore a new and not-so-far area. So, where did we go? KENTUCKY.

Turns out, Kentucky is pretty darn convenient to get to (only an hour flight out of Detroit via Delta) or a five-hour drive if you head into Lexington. But most importantly, it met two of my core criteria – whisky sampling aplenty and proximity to some stellar hikes. Bonus points that with some proper planning, I felt like we could make this a legitimately fun and family-friendly trip.

Smoothies for the win at Greyline Station in Lexington, KY

Like we do with most of our travels, we split our stay into two nearby destinations: Lexington and about an hour’s drive away, Red River Gorge, a prime hiking park rich with geological features and cool lodging options.

Breaking down our itinerary in three, two, one …

DTW selfie


Fly into Lexington’s Bluegrass Airport via a just-shy-of-an-hour direct Delta flight out of Detroit Metro Airport first thing. (Normally, we’d drive, but we were going for birthday specialness here.) The airport is relatively tiny and easy to manage, with only a couple of luggage claim carousals and rental car desks within the same space. We rented a midsize sedan for our stay and it worked perfectly; there was no need for anything bigger or with four-wheel-drive.

I’d done a lot of online research on which distilleries were welcoming of children since we had a two-year-old in tow. Woodford Reserve was not one of them, based on the few articles I’d read, but it consistently ranks among the best to visit, located out among rolling thoroughbred farms. I had opted not to book a formal distillery tour (note: reservations are required and fill up fast and typically open to reservations around three months in advance), and instead, see if we couldn’t arrive *right* as their open-to-the-public bar opened, so that at minimum, we could take a quick look around and have Trevor properly kick off his birthday weekend with a high-quality bourbon tasting. Somehow, it worked. We arrived right around 11 a.m., when the bar, located across the street from the distillery’s Main Entry building and gift shop, opened its doors. We were the first ones in and Trevor promptly ordered a $75 tasting of the line’s finest bourbons. I took advantage of a free mocktail… and within five minutes, Mack had “cheers’d” my cup too enthusiastically and sticky mocktail mule went everywhere. We were totally those people. And the staff wasn’t particularly forgiving. Thankfully, we were still the only ones there and we don’t take things personally :) I’m calling it a success and don’t regret it for a second. The drive out to Woodford Reserve alone is beautiful and worthwhile.

Thankfully, no bourbon was spilled
Why wouldn’t you kick off your trip with a bourbon tasting?

Getting food in bellies was the next goal and I’d found the Greyline Station while hunting around Instagram, a public marketplace in a historic building that long served as a bus and transit company depot. Inside, we popped into B’Juiced for a quick smoothie, grabbed doughnuts (for later) at North Lime Coffee and Donuts and then sat down to eat a wholesome, warm meal at Nourished Folks.

The setting is casual and the site is a great one to stroll around, grab a quick bite, and then be on your way.

Walking Greyline Station and its shops
North Lime Coffee and Donuts

With a couple of hours to kill before we could check into our first accommodation, we then headed over to the much-hyped Kentucky Horse Park. Mack has seen horses from afar and seemed particularly interested, so I figured he’d get a total kick out of this, which despite being in lean winter programming mode, still offered a chance to get up close to some stunning animals.

Somewhat surprisingly, we all enjoyed ourselves. Walking the stalls, peeking in at the horses and winding our way through the museum was really interesting, even to someone with zero knowledge on horses or horse racing like me. We timed our visit to ensure we’d get a chance to join one of the “stallside chats” and see a horse up close and it worked out that we joined the talk at the Hall of Champions, where legends like Go For Gin and Funny Cide are spending their days in retirement; Mack even got to feed million-dollar-winner Point Given a peppermint out of his hand, which was such a sweet moment.

In the summer months, guests can take advantage of horseback trail and pony rides.

That afternoon, we headed to Lexington’s Distillery District, where a small set of buildings offer bourbon, food, ice cream, coffee and a small shop or two. It’s a casual, family-friendly setting and luckily, I’d found an Airbnb property housed right within it; on the third-floor of the distillery building, to be exact. Dubbed “Top Shelf,” the rental property had a big outdoor deck with seating and gas grill, a cozy open living space, soaking tub in the master bath, and three decently sized bedrooms.

We checked in and spent the afternoon and early evening kicking back. The place was perfect for us, but it’d be even better suited for a small group of bourbon-tasting adults who can take advantage of the Distillery District’s live music and ax throwing venue.

The Airbnb staircase features iconic race horses names and times
See our Airbnb patio lights along the left side of the distillery building?
Cozy inside the open-layout living area, kitchen and dining space

Dinner was as easy as walking down two flights of stairs. Just beneath our Airbnb was Goodfellas, a local chain that offered really, really good pizza. It’s the type of place with a line at the door; mostly because you order your food as you walk in and then find a seat at the bar or a table to chow down. The locals in front and behind us in line vouched that it was the city’s best. (Pro tip: Order a mile-long breadstick, too.)


Who doesn’t start two days in a row with bourbon? After a lazy morning, we grabbed coffee and croissants to go from Brevede Coffee Co. and then me and Mack hung out in the sunshine while Trevor popped into the James E. Pepper Distillery, just beneath our Airbnb, for a second tasting. Slow and steady, folks. Like the first, this was a sampling of three small pours and an opportunity to buy a bottle of his most-liked tasting to bring back home.

This tasting room is pretty small, with a short bar and only a few tables. It would have been a fine space to bring a small kiddo into, especially if they were in a stroller.

James E. Pepper Distillery tasting bar

Having checked out of our one night at Top Shelf, it was time to head out of Lexington and toward Red River Gorge. Only an hour drive from Lexington, we were headed to a small, rustic cabin, built alongside a massive rock wall in its own private gorge. While the rental itself wasn’t much to write home about, the property that it sits on has its own waterfall, a great fire pit and a hot tub – and all within a 20-minute drive to some of the area’s best hikes. Most importantly, perhaps, it was rated five stars with 250 traveler reviews. At the time I booked, I was sold, and by the time we left the rental two days after arriving, I was sad to say goodbye.

The VRBO, built against a massive rock wall on a property with its own hike-to-see waterfall
The master bedroom (plus two, semi-private loft beds up a ladder)

From a creek that ran through the property (which Mack happily threw stones into for an hour) to the steep hike up to the cabin, we loved the little slice of serenity against the imposing rock wall. Not to mention, the price was right, at only $188 per night, on average.

Technically in Natural Bridge State Park, this is a two-mile hike that begins at Lakeside Trail and climbs 400 feet through pretty forest to a natural arch formation that offers views from underneath and an expanse to explore on top, after you’ve squeezed through a narrow rock staircase to ascend.

We hiked just before dusk, and soaked up the views as the sun set, explored a bit and then headed back down. The park closes as soon as the sun goes down, and you don’t want to be hiking downhill in that terrain without a light, so be sure to come prepared if you’re a late afternoon hiker.

Also, a BIG note if you’re traveling with little ones: EVERY hike we did in Red River Gorge included steep drops. Like, very steep. Because we had Mack in a backpack carrier, this wasn’t an issue; and we were able to find plenty of safe spaces to take breaks and run around. However, if you’re traveling with kids who are too big or unwilling to do the backpack thing, you’ll want to ensure that they’re at an age to be trusted and understand the risks of hiking.

Natural Bridge State Park
Oh, hey!
Dusk hikes


Approximately five miles round trip, this was our longest hike of the weekend. The trail winds along a ridge that offers spectacular views on each side, and the impressive Courthouse Rock serves as the finale (well, sort of, since it’s a roundtrip hike). The elevation is about 800 feet and there are plenty of stunning views to take advantage of. (Again, steep drops, too.)

We met a friend for this hike, so had an extra set of hands in corralling Mack, which was helpful when we stopped to picnic. But for the most part, this hike required our entire afternoon.

(If you’re curious, our morning included coffee outside, creek splashing, and a toddler nap. And our evening included grilled steaks and a hot tub soak before falling into bed.)


Just up the road from the cabin rental was Brandenburg General Store, which also touted ice cream and shakes. To compensate for the sadness of departure day, I kicked off Sunday with a pina colada shake, which I highly recommend.


With an early evening flight, we weren’t in any rush to leave, so we headed out for one last, simple hike. Sky Bridge Hike is an ultra-easy .75-mile loop that canvasses another gorgeous natural arch on the east side of the park. It’s near several other short, scenic hikes, and makes a great stop for your first day or your last.

Sky Bridge Trail, Red River Gorge

One. Last. Distillery. We stopped at the Spanish-style Four Roses Distillery on our way out toward the airport, since it wasn’t a far excursion. I’d made this single bourbon tasting reservation for Trevor since it was inexpensive, didn’t include a tour, and available at the right time given our travels. In this case, the tasting was done in a classroom setting (definitely not toddler friendly), and provided a slew of educational information on the bourbon distilling process and tasting exercise.

I chose not to attend for the obvious reason that I chased the baby, but Trevor enjoyed the stop and it was only half an hour – a good stretch to run out some energy before heading to the airport and boarding a flight back home.

There you have it. A weekend that celebrated our 40-year-old, with some city-centered exploration and libations, some rustic outdoorsy goodness, and whole lotta family fun. I’ve got to say: Kentucky impressed us all.

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