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Roasted Heirloom Tomato Pie

Posted by on September 1, 2014

Living in the Farm Tour Capital of Kentucky, Oldham County, there really is no way I can visit a market and not take a gander at all the gorgeous, colorful, yet ugly, heirloom tomatoes! This is my Roasted Heirloom Tomato Pie recipe based on those sugar babiesThe story comes from a long list of Amish and children’s home memories, has a chef from North Carolina thrown in for good measure, and ends with my Labor Day weekend recipe that’s not only easy, it’s elegant, and quite simply DELISH! It continues to amaze me that heirloom tomatoes are grown from seeds that have been passed through the generations – for at least 100 years! Can you imagine the foodie memories attached to those tomatoes!

It was Saturday morning of Labor Day weekend and, unexpectedly, Greg woke up sick. It had been over a month since he and I had gotten to go fishing, but this weekend was supposed to be the time! We had planned it all summer. We love fishing and being outside, being on the water, and just spending time together in the serenity of woods that surround the lakes we fish in. Fishing is our way of relaxing, of clearing our mind, and coming down from the hectic ways of the week.

We had planned on heading to Rough River for Labor Day weekend until the threat of severe thunderstorms rolled in mid-week and threatened to keep us inside the whole weekend if we went. But it’s a long drive to Rough River just for a day. The trip requires at least a 2-night stay, our tent “condo” – as my niece Ashleigh calls it, packing a cooler to the brim, actual grocery shopping, and the trunk stuffed to the gills with blankets and tackle. After watching the weather all week, we decided that if the weather at Rough River was not going to cooperate with us staying in our “tent condo” without the threat of carrying us off like Dorothy and Toto, we would just stay home and go fishing at Lake Jericho in Henry County for the  day. Either way, we would fish!

After Greg woke up sick that morning, we thought we’d just try heading to Lake Jericho for a little fresh air to see if that was the cure for what ailed him! The rest of the weekend was still up in the air, but that day, we would fish! We fished for sure, but the fish didn’t start biting until it started to rain on us. Needless to say, we fished too long in the rain and got caught in a cold downpour before we made it back to the car! This was not good, and certainly didn’t help cure what ailed him.

I knew Greg would likely be sick again tomorrow since we had gotten caught in the rain. I also knew that I would have some time on my hands while he recouped. He’s a lot like me in that when he’s sick, he really just wants to lie on the couch and watch TV in hopes of sleeping on and off all day. He doesn’t want much. And with a sore throat, he surely wouldn’t be much for conversation either. Hhhmmm. What to do with myself?

I woke up the next morning with all kinds of energy! This kind of energy usually rears its head on Saturday mornings for me. There’s something about waking up early on a morning that you know you don’t have to work the next day. It’s almost as if your mind has permission to just relax and be creative. It’s OK if you have a long list of things you actually want to do that day. If you want to get some work done, that’s fine. But you’re working because you want to, not because you have to. Sound familiar?

I got up, drank almost a pot of coffee, and tried to figure out what my mood was telling me to do. WORK. That’s what it was telling me to do. I had a small work project to finish up and I needed to do my normal cleaning things. GUILT. That’s my issue. I feel guilty when there’s work to be done, so I can’t enjoy anything else until I take care of what’s pressing on my mind. That’s one reason I pick up around the living room before I leave the house. So I don’t come home, see a mess, then feel like I have to clean it up before I can sit down and relax.

So, I went ahead and finished my work project. Then I finished laundry – including the bed sheets – cleaned the bathrooms, dusted the furniture, and all those usual weekend chores. While I was loading the dishwasher, I heard a lady talking on TV about tomato pie. My ears perked up! I realized it had been a couple of years since I had made my tomato pie! I started the dishwasher, grabbed another cup of coffee, and quickly sat down on the couch in the freshly cleaned living room to watch this tomato lady!

The KET show was called,  “A Chef’s Life.” I had never seen it before, but sooooo right up my alley! Chef Vivian Howard owns a farmer’s market restaurant with her husband in North Carolina called, “Chef and The Farmer.” The lunch menu at her restaurant that day was based on the heirloom tomato. Not only did Chef Vivian strive to make the perfect tomato sandwich (complete with homemade onion bread made at the restaurant), she made a gorgeous tomato pie with a twist – she roasted some of the heirloom tomatoes. What a great idea! I watched as she visited tomato farms and taught her staff the importance of less-is-more. What a great restaurant concept and a great tourism attraction for North Carolina! Her restaurant will certainly be a stop for me the next time I’m in North Carolina! I was now inspired to be creative with my own tried-and-true tomato pie recipe!

As I thought about my recipe, I continued on with my creative day – soldering a stained glass project I had set aside, organizing my tourism office, designing a marketing piece for a friend, then the cooking bug hit me! The last time I made my tomato pie, I baked it for breakfast guests at Bluegrass Country Estate Luxury B&B in LaGrange, KY. Cheryl, the innkeeper, had asked me to stay there with her guests while she was in California with her family. The guests of the inn were from up north, so I decided to make them a true southern breakfast in an elegant way – hopefully a breakfast that would create memories of their first visit to Kentucky.

I remember asking myself, “could I make Tomato Pie elegant enough to serve in a luxury B&B?” That was my question at the time. I gambled with my usual tomato pie recipe, and they absolutely loved it! They did confess afterward that they feared trying something that made no sense to them as northerners – but only after finishing off 2 pies, fresh scones, roasted fruit on yogurt with homemade granola, and my candied peppered bacon! My recipe was an old family recipe passed on to me by my grandma, Nan, and it hadn’t failed me – again!

But after getting bit by the tomato bug and wanting to experiment, I realized that there were no local farmer’s markets open on Sundays. I opted for Earthfare. Earthfare just proves that even larger stores are listening to the public’s cry for true farmer’s market ingredients! I drove to Earthfare, purchased 2 kinds of gorgeous, colorful heirloom tomatoes, 2 kinds of cheeses, an organic pie crust, and drove home excited to get started on my new recipe! I walked in the door at home, showed Greg my fabulous finds while he was half passed out on the couch, then proceeded to the kitchen to whip up some magic of my own, while he slept and recuperated. I thought he might be up to a taste of my new masterpiece when he starts feeling better, but until then, the smell of sautéed onions and roasted tomatoes couldn’t be a bad thing for him!

It’s funny, when I started to prep my ingredients in the kitchen, dicing tomatoes, sautéing onions, and tasting at every turn, I remembered my days as a kid in the children’s home. I remembered planting, growing, and picking tomatoes from our garden. I remember thinking how there was always something I would rather be doing than working in that damn garden. I remember thinking how ugly those tomatoes were and how unappetizing they looked all covered with dirt and dried-on leaves from the heat. I remembered the Amish family I grew up knowing down the street.

Sometimes we kids would go to the Amish family’s home to help clean up when the river behind our property would flood. I remembered the time we were there helping, and the women of their family were making all kinds of racket in another room. When I looked into the kitchen, they were all gathered around a table full of tomatoes of every color. They were slicing, steaming, peeling, cooking, canning, laughing, and having a good time. The older ladies were teaching the younger ones to taste as they went along. I was watching traditions that had been passed on to them by their moms and all the moms before them. More than 100 years of heirloom memories and stories went into every sterilized jar of tomatoes.

I’m sure when they’re using those tomatoes throughout the year, they relive their foodie memories – created together in that kitchen. Even though I never saw them make a pie from those tomatoes, and they never saw me watching them with their tomatoes, I would venture to guess that they had no idea they are part of my childhood foodie memories created that day. Childhood memories that are colorful, “home” grown, juicy, sometimes ugly, but always DELISH!

Roasted Heirloom Tomato Pie Recipe

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  • Yield: One 9 (6-8 Servings)
  • Prep:
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This recipe is a sophisticated, yet easy, creation that showcases 2 types of heirloom tomatoes, one chunked then roasted, and one in all its raw glory as a black cherry tomato. You can also skip the tomato roasting step if you want to save time! It's simple, elegant, and DELISH!



  1. Preheat oven to 400 degrees (at 400 degrees, you can also bake your pie shell if you need to). Note: you will lower the oven temperature later to 350 degrees. If you are skipping the tomato roasting step, set oven to 350 degrees now. Line a baking sheet with parchment paper. Set aside.
  2. Meanwhile, in a saucepan, heat olive oil and butter on medium heat. While your pan is heating, slice onions, then add to heated pan with the olive oil and butter. Sautee onions until browned, about 30 minutes. Remove from heat and set aside.
  3. While sautéing onions, chunk 2 large heirloom tomatoes. Transfer to a large bowl then drizzle with olive oil and sprinkle with salt and pepper. Spread tomatoes in a single layer on parchment-lined baking sheet. Bake until tomatoes have browned and somewhat dried (roasted) - 45 minutes to an hour.
  4. In the meantime, slice raw cherry tomatoes in half and place in a bowl, then top with chopped basil.
  5. Next, in a separate bowl, mix mayonnaise, yogurt, and cheeses. Pepper to taste. Because of the parm cheese, do not add salt to mixture. Set aside.
  6. When hot roasted tomatoes have come from the oven, lower your oven temperature to 350 degrees. Spoon roasted tomatoes into the bowl with cherry tomatoes and basil. Fold to combine.
  7. Layer sautéed onions on the bottom of your prepared and baked pie shell. Top with tomato mixture. Spoon and spread your mayo yogurt mixture on the top, leaving a 1/2 inch uncovered around the sides.
  8. Bake for 30-45 minutes until top is bubbly and a little browned. Take out of oven and let rest for an hour before slicing into wedges. Best served at room temperature or slightly warm. DELISH!

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