"Letcher County"


hrs on the road


communities visited




photos taken


The Plan

For episode 5, we knew we wanted to go explore somewhere brand new that we hadn’t really been to before. After a little research and help from friends, we landed on Letcher County, KY! This trip was another overnighter, complete with a comfy stay in a beautiful, local Airbnb.

What We Did

Salyer House Airbnb

Per the usual, we started off our morning bright and early, packing the cars and departing from our home office around 6:45am. Everyone was in high spirits to get the show on the road and get to our home for the following night.
Upon arrival in Whitesburg, we were greeted by Whitney, our point of contact, and Missy, the owner and designer/renovator of the Salyer House (built in 1924!). Easily one of the most stunning restored historic buildings we’ve seen on our adventures, the house features six different suites available for rent, or you can rent out the entire house, which is what we did! After meeting Missy and Clay, who was our guide for the day, we dropped off our bags and headed out on the day’s exploring.

Little Shepherd's scenic Trail

If you’ve ever wanted to go on a near-infinite driving loop through the forest and mountains, Little Shepherd’s just might be the trail for you! Clay led us along a twisty driving road that takes you through the Kentucky Mountains right into the Kentenia State Forest- the oldest, state-owned forest in the country. We drove with the windows down and music up, stopping at a couple of
different overlooks to take in the views along the way. We were all starting to get a little hungry, so it was time to drive over to the general store to grab some snacks!

The General Store at Creek Crossing

Almost as soon as we stepped out of our cars at the general store, we were warmly welcomed by the owners and all things Appalachia! 

The store is the last stop before you cross over Pine Mountain, so they offer a variety of grocery and household essentials. Tiffany, the owner, was able to share some unique stories about customers and connections that she and her husband have in the area. It was obvious that the store means a lot to the locals and we loved getting the full experience.  

The Stables at Creekside Glen

It wouldn’t be an EA trip if animals weren’t involved somewhere! After fueling up til lunch, we headed to the stables to check out their summer activities in action, complete with horseback riding for all ages/abilities. While Natalie and Cassidy interviewed Drew, the owner, James tried to make friends with a goat while Kaitlyn and Sydney watched…that went about as well as you would expect. 

We wanted to fit in a local hike before lunch, so after saying goodbye to everyone, we were off!

Bad Branch Falls

Bad Branch is a hike that’s really popular with the locals. A couple of us had been there before and loved it, so the whole team was stoked to see it. The trail was cool and shaded, surrounded by a plethora of trees and sandstone. The hike to the falls was fairly easy until the last ¼ of a mile or so, which had us semi-scaling some large rocks. 

It was absolutely worth it! The falls tumble off of a rock ledge to a creek about 60ft below. Talk about a low effort-high reward hike. After admiring the waterfall for a bit, our stomachs were really starting to growl, which could only mean one thing…lunchtime!

Pine Mountain Grill

The Grill is known as one of the best restaurants in Letcher County, so obviously, we had to make a stop. The entire menu sounded delicious, so we had a hard time picking, but eventually decided to go with variety and try as much as possible. 

After we finished fueling up, it was time to head back out there! 

Southdown Farms

Sydney was easily the most excited about the visit to the farm, as her family also owns a farm and does some small-scale organic farming. The owners of Southdown, Seth and Sheryl, were some of the kindest people we’ve met and welcomed us with smiles and maple syrup- yeah, that’s right! They tap their own maple trees and produce their own syrup. They also grow a host of fruits and vegetables, which they sell at farmers markets and share with their friends and neighbors. 

After getting a tour and educational conversion about farming in Appalachia, we said goodbye to Longs and drove to our next stop. 

Kentucky Mist Distillery

Moonshine is a pretty big industry in the South, and KY Mist is no exception. They were making some peach moonshine when we got there, so Colin, the owner, gave us an overview of how the process works and gave us a taste-test. Moonshining has been in his family since the 1900’s, and he’s continuing the legacy by creating craft beverages with family recipes and trade secrets every day. 

After the moonshine talk, it was time for some golf!

Raven Rock Golf Course

In case you haven’t been able to tell already, we’re big fans of golf, so everyone was stoked to hit the course!  While Chase, Josh, and Kevin *really* play golf, we’re all trying to get better at it, so this was the perfect opportunity for a lesson or two. 

While Kaitlyn and Cassidy worked on their long drives, Natalie and Sydney decided to explore the course for themselves via a slightly wild golf cart ride. We all met back up on one of the more difficult holes, complete with a view of the KY mountains making up a perfect backdrop for the afternoon. Chase gave the course the high rank of 9/10. What more could you ask for?

After a couple hours of golf, we headed to Fishpond Lake to– you guessed it– fish. 

Fishpond Lake

Fishpond Lake is man made and stocked with rainbow trout, catfish, and other species. Kaitlyn was especially excited to be there as fishing is her ideal way to spend an afternoon. While she, Kevin, and Cassidy all fished, everyone else skipped rocks and explored the shoreline. Unfortunately, we didn’t catch any fish, but we had more important things to move on to- catching the sunset!

Pine Mountain Overlooks

One of the most beautiful parts of Letcher County is the view of and from Pine Mountain. There are several overlooks that wind up the side of it, so we knew we HAD to watch the sunset from at least one of them. We made it up to the highest point we could pull off at, and hung out for a bit to watch the sun go down.

Once it was nearly dark, we headed back down the mountain to downtown Whitesburg to eat dinner.

The Veranda

We enjoyed our meal from Pine Mountain Grill so much that we ordered take out from there for dinner! We took our food to a local space located downtown called “The Veranda” that is a historic building in the process of being renovated for community events and celebrations. 

After we finished eating and hanging out with Clay, we headed back to our Airbnb (the Salyer House), where we called it night and hit the hay.

Who We Met


Whitney was our point of contact for setting everything up with our adventure day! She was a huge help with scheduling and connecting us with the right people. 


Missy was our amazing hostess and the queen of Letcher County. 


Clay was our friendly guide! He made sure that we saw the very best parts of the area and kept us from getting lost more than once. 


Tiffany is the owner of the General Store and lover all of all things local to Whitesburg. 


Drew is a horseman extraordinaire and the director of The Stables at Creekside Glen.

Seth and Sheryl

Seth and Sheryl are arguably the best maple syrup crafters in the state of KY.


Colin is the moonshine master of Kentucky Mist Distillery.

What We Ate

Just about everything we tried at Pine Mountain grill was awesome! Our hosts graciously gave us the famous meatloaf and the open-faced roast beef sandwich to try as appetizers during lunch.  Luke ordered the pulled pork sliders and was a big fan, and said that the french fries were some of the best he’s ever had. The chicken stir fry and sweet potato fries were also team favorites!


The General Store did not disappoint either. From a variety of Ale-8 and Grippos flavors to local baked goods and other snacks, the store was the perfect mid-morning place for us to stop for snacks.  Chase picked up some of the Grippos BBQ cheese nibs, which left him amazed, and the homemade turkey sandwich ranks high on Natalie’s totem pole. The variety of local root beers and teas impressed Kevin, and several of us also bought  some of the baked goods to take on the road. 

What We Saw

Kentenia State Forest

The oldest, state-owned forest in the country. The Little Shepherd’s driving trail winds its way through. 

Bad Branch Falls

A 60ft. waterfall surrounded by trees and sandstone ridges. 

Fishpond Lake

A lake, that’s also a fish pond…because fish live in it…and you can fish. 

Pine Mountain Overlooks

The place to be if you want the best sunset view in the area. 

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