Evening Shade Farm: How Twin Sisters Built Their Dream Farm in Kentucky

Twin sisters Leigh and Anne Walkup, the women behind The Southern Lady Cooks and Front Porch Life Magazine, have brought their lifelong dream to life at Evening Shade Farm in Kentucky. From restoring a 100-year-old home to building a cooking cottage for their business, they share how hard work, perseverance, and passion turned their dream into reality.

This story is just a glimpse into our full interview with Leigh and Anne Walkup. The complete interview originally appeared in a past issue of Front Porch Life magazine, where we share inspiring conversations, timeless recipes, and heartfelt features in every season. By becoming a member, you’ll gain access to all of our past issues, exclusive interviews, and the kind of Southern stories you can’t find anywhere else.

A Dream and a Vision

Evening Shade Farm seems like a dream come true for both of you. Can you share the journey that led you to purchase this farm? What inspired you to take this leap?

““This journey has been many, many years in the making. We have been trying to buy a farm for 3 years, but this decision started over 20 years ago when Leigh and I were met with some bad circumstances around our family farm. We lost our heritage and decided them we would regroup and make our own way. This has been a lifelong dream, and it feels really amazing to see it come true.”-Anne

What were the key factors that made Evening Shade Farm your “dream farm”? Was there a specific moment when you both knew this was the right place?

“Actually, we looked at Evening Shade three years ago and passed. It just goes to show that timing is everything. When we looked at it before, it was a dreary winter day, and I just didn’t feel like this was the place. The kitchen was tiny (as you know, we cook for a living, so I had a vision of a big luxurious kitchen!), and the barn was not what I had envisioned, so we quickly passed. Then, three years later, after looking at countless farms, we sat down and went over our checklist and realized that Evening Shade had it all. We quickly scheduled a day to go back and see it, and this time, when we drove into the driveway, I just knew that it was it. Like I said, timing is everything! Oh and now that I am in the home, I love my little galley kitchen.”-Leigh 

Overcoming Challenges

Running a farm and a publishing business simultaneously must be quite challenging. How do you manage to balance these two demanding aspects of your lives?

“You know, fortunately me and Anne kind of feed off being busy. Don’t get me wrong, I want my downtime and quiet as much as the next person, but running these businesses is fun for us. For example, one day last week, we were moving hay out of the fields at Evening Shade. Anne is in the truck hauling hay out of the fields while I’m making lunch for everyone in the house. Mom calls and says she has two recipes made, so we leave the farm and drive to her place to photograph and style them. Then back to the Evening Shade to do two hours’ worth of mowing. Then back to Anne’s to feed the horses and then back home to upload and edit photos, write newsletters, etc. To me and Anne..this is fun! Of course, it’s not always fun, not every day do all the things get done. So we just see that day for what it is and keep it moving.”-Leigh

Can you share a time when you faced a significant obstacle in making your dream farm a reality, and how you overcame it?

“Every afternoon for three years, Anne and I would spend an hour looking at land online, trying to find any piece of property that we thought would work. We even looked at bare land and mapped out where we could build the barns, the houses, and the cooking cottage…we honestly looked at every single angle. We knew that Anne would be moving later (Anne and I bought a place in our 20s that is five acres and a house that we all love. She lives there.), so it didn’t necessarily have to have 2 houses to start off with. So, just finding the vision that was a big obstacle! We actually made an offer on two places before we got Evening Shade. I’m forever thankful those didn’t work out for us!”-Leigh

Inspiration and Passion

You both run The Southern Lady Cooks and Front Porch Life Magazine, which celebrate Southern culture and cooking. How do these passions influence your vision for Evening Shade Farm?

“Oh gosh, they embody this farm so much and this farm just brings that whole vision full circle. Our heritage began with our grandmother, a wonderful hostess who always experimenting in the kitchen. My grandparents owned a beautiful farm, and her energy was one of the main reasons that farm was so magical. She loved her porch and having wonderful conversations with friends and family—spending time in her garden and just being a beautiful Southern woman. We always wanted that in our life and owning land really felt significant to both of us. This farm has that same energy, which Leigh and I brought with us. We have patiently waited for this chapter and as soon as we could get our feet on this property the energy shifted. We both feel our grandparents’ presence and our Dad’s and it so calming and comforting to experience this together. We have worked hard to put that same soul into The Southern Lady Cooks and Front Porch Life and this beautiful farm just completes the circle.”-Anne

For those aspiring to make their own dreams come true, what advice would you give about the importance of perseverance and hard work?

“My best advice is never quit and never veer to far away from the vision. You can make adjustments, make small changes but the original picture was there for a reason and if you always keep that in sight, you know what you are working toward. Hard work pays off, so never let off and just keep working toward your dream. I also believe in dreaming BIG! Life is too short to play it small and make it fun. Leigh and I would talk about our “new” farm daily..long before we ever found it, we designed it, talked about what our days would look like, all of it, and we had so much fun with the process. Also, your dreams don’t have to make sense to anyone but you and don’t let others influence you. Many people love to give their opinions, but it’s not their life and they are not living it for you. Most of those opinions come from people who don’t have a clue what your vision is and they are not owed an explanation. Your dreams are yours for a reason. “-Anne

Unlock Every Past Issue

This is just a small snippet of our whole conversation with Leigh and Anne about their dream farm, which you’ll find in a past issue of Front Porch Life magazine. Members get access to every past issue filled with inspiring interviews, timeless recipes, and behind-the-scenes features you won’t see anywhere else. If you loved this excerpt, you’ll enjoy diving into other favorites like Childhood Meals We Still Crave or Southern Roots and a Family Legacy, along with dozens of stories that celebrate the beauty of Southern life. Join our membership today and unlock it all—every past issue, every recipe, every story waiting on the porch for you.

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