Rewind + August: Letting go + Impromptu session | Middleburg, VA

Today’s tidbit: “Life is not made up of minutes, hours, days, weeks, months, or years, but of moments. You must experience each one before you can appreciate it.” ― Sarah Breathnach 

Earlier this week I was finally able to share a freelance project I worked on with GMU (read more). Today is another post from August that got pushed back. The last few months have just been so busy and eventful! As you’ve seen with all of my Old Town Alexandria sessions, I love wandering around and taking in the beauty + charm… and Middleburg, VA certainly has that. This truly was an impromptu shoot, however, as I reluctantly was heading to Middleburg to drop off most of my riding things and let go of that chapter.

A little background… in August, our childhood house was sold and were busy sorting through the last things to pack (read more). There it was in the basement–my horse corner. My big navy tack truck that had been in front of Baileys stall… a collection of things that had formed my riding life for so many years. It is always hard to walk away but I knew it was time to let go. It was time to sell everything I wasn’t using so someone else could get good use out of things I so loved and that had created so much happiness. It wasn’t the things though, but rather what each represented…

Sneak peek image: One of my favorite show pictures at Fox Chase Farm, in Middleburg, VA


Be sure to click below to read more and check out more pictures. Enjoy!

{Memories + Show days} Below are only a handful of my favorite pictures from my show days. Waking up at 4am to head to the barn to load Bailey in the trailer. So many feelings rushing through me as we’d be driving to the show, full of excitement and nerves! Spending ALL day preparing, watching + taking pictures of others, and of course riding. I wouldn’t trade those days, experiences, moments and memories for anything!

Isn’t Bailey just adorable? Such a fancy little pony, and totally knew when he was at a show.








{Letting go} As I mentioned in the beginning, I finally decided it was time to let go of my horse stuff before moving to the new house in Maryland. From show clothes, entry numbers and my show binder full of notes and pictures to miscellaneous tack, grooming supplies, blankets and saddle pads. I knew it was time to sell everything I wasn’t using so someone else could get good use out of things I loved and that had created so much happiness.

It wasn’t just a show shirt or tall boots, but rather the memories that were formed and what each represented… from buying it to using it. My old trainer, Jana and I would make a day out of it… heading to the Tack Exchange searching for great new finds, while also learning about different tack and riding things. We’d spend hours in there. Then we’d walk the charming streets of Middleburg to a local cafe for lunch together. It always turned into a mini road trip, complete with singing and 80s music. There was never a shortage of stories and laughs shared. Holding that show clothes brought back memories of not only buying it like I mention but also when I wore it. I can remember exact shows when I used something and so many details about it. From how I was feeling to how a certain class and course went to what new people Bailey and I met and interacted with. There are SO many memories there!

Ironically, Middleburg Tack Exchange is where I spent a lot of time hunting for some of these great finds and where I ended up taking everything to sell. I know the things don’t really matter though, and as hard as it was I let them all go (minus a handful of things I have kept) I know someone is getting good use out of them now. The memories are worth more than anything. I cherish that time and am thankful to have had Jana, such a wonderful supportive trainer and friend… as were all of my trainers (Terri at Clairvaux, Jana at Anyplace Farm and Jess at Cut to the Chase). I am happy to say we still keep in touch!

I had taken pictures of everything I dropped off at the Tack Exchange but when my laptop decided to clear iPhoto in September those were lost. First picture below is from my phone.




{Middleburg charm} After that emotional morning, I decided since I was already in Middleburg to walk around and do an impromptu {little details} session. Every place has something unique to offer and I enjoy finding those little details and hidden treasures others may just walk by. I drive a lot of my friends crazy, always stopping to take a picture, but it’s how I am!

There is just something about being back in horse country, in Middleburg and so close to Upperville that I love. It’s a feeling of contentment… like when I’m around horses and at the barn. I can’t describe it but after all these years it still has the same effect!























… And that was an August afternoon. Now you have a little background on riding and show days, and although it was a rough morning taking everything in to sell I know it was time. I am glad it was such a beautiful day and was able to enjoy the charming town walking around like I used to, and of course taking pictures!

Have a wonderful weekend!

6 Responses to “Rewind + August: Letting go + Impromptu session | Middleburg, VA”

  1. Jana says:

    For some reason, at a point in our lives, we horse girls feel as though we need to leave horses behind. In reality, we just need to realign our relationship with the sport.

    It is always interesting to me to hear you girls talk about your experience and impressions and takeaways from your time with me. Aside from teaching you all how to use the F-word at the appropriate time, I like hearing what else you learned or felt or cherished.

    Those are certainly times we will all never get to duplicate. I decided at 40, I needed to stop teaching and do my own thing and I think that was good timing. All you girls were graduating high school and heading into college. I hung on for everyone to finish out their senior years. So, that was a chapter closed.

    Some things that were really important to me when I taught you girls was that you learned to be organized, responsible, competitive and brave. And, because it is such an expensive sport, I wanted you all to look the part for less so I taught you all how to braid and properly groom for the shows and made sure everything was spiff and polish. Lessons in dedication and persistence were a given. I wanted you all to be able to go to another trainer and not be a bunch of bumpkins. And I wanted you to be able to pass on whatever you learned from me (except the F-word) to someone else. I loved teaching you how to win and it was always amazing to see how once you girls got it, you were ALWAYS the winners. Nothing made me happier than seeing you girls come out with the blues and the tri-colors. It was a fantastic formula and process that I’d developed from the time I was 18 and it was neat to see it work on rider after rider. Once you got it, it was yours and it never left you.

    I wanted to give everyone what I didn’t have as a kid. Not that my parents wouldn’t have given me the same support. They just didn’t know what to give. Neither did I. So once I learned it, I didn’t want anyone else to be without it. And as a kid, I didn’t want my parents around which was SUCH a mistake. That means there are NO pictures from when I was a kid riding. Well, there are very few. In looking at your horse pictures above, there are at least 6 that I know I took of you and Bailey As you remember, I ALWAYS had my camera with me and took SCADS of pictures of you girls. I have boxes of them. I charged $45 for my day fee, took pictures and processed them as double prints which meant they ran me about $20. After I bought my breakfast, lunch, and sometimes dinner and processed the pictures, I made no money whatsoever! But, that wasn’t the point. The point was, I wanted to coach you to the win, to give you a ton of confidence and lots of wonderful memories. With all that accomplished, I know I did my job.

    I really, really cherish all those times and I do wish I could have them back. But man, that was exhausting! Hahahha! So, now, you need to do what I do. I ride twice a week at a nice fancy place where they tack the horse up for me and I go out and play and have fun. I never thought riding once or twice a week would be as fulfilling but it truly is. So, you don’t need to leave horses because your life changed. You just aren’t at the barn at the moment. Go when you can. Once it is in your blood, it never leaves you. You’ll always be a horsewoman.

    Thank you for your nice post and all the wonderful things you said. It made my day.


    • alyssa says:

      I love this! It is so true.

      Although a huge part of it was riding, there were many life lessons and important things taught that have shaped me. As you said we learned to be organized, responsible, competitive and brave. We learned confidence, dedication and persistence. When we first worked with Bailey, you know better than anyone the dedication it took to stick with him testing and challenging everything. Once you ‘Janatized’ him though, he figured it out and went from a monster to a fancy show pony… and now is packing around little kids, as sweet and careful as he can be. Amazing.

      You went above and beyond in every way for us and expected the same in return. All the mistakes and falls turned into lessons that pushed us to go further than we thought. High school is a rough time and I am SO glad I had riding and you to turn to! You definitely taught confidence and created lots of wonderful memories… and 100% did your job! Truly.

      You always had your camera with you snapping away, which was so appreciated. We all know I did as well when I could, but when I was riding it was nice to have those shots and videos taken to look back on! So valuable. Not something the normal trainer would do, but you weren’t normal… you were amazing and so generous in every way!

      I’m glad you cherish all those times too! I really have nothing but fond memories looking back… even with those countless hard falls and disaster courses because it made me stronger. I really had to work for it and the wins down the road were that much more rewarding! There really is so much I take away from it all and you will always be someone I respect and look up to. Thank you for everything!

      I know I will always be a horsewoman and it’s in my blood. While it was hard to say goodbye to the show days, it was a huge commitment and exhausting. It shaped me and I’m enjoying riding just for fun now. Next week there will actually be a post on fall at the barn (where Bailey is).

      Thanks for your thoughtful comment and I’m glad I made your day 🙂 I meant everything I said!

  2. Karen says:

    Oh yes all those memories of the lit’l pony will forever be in our hearts and minds. Jana, you were so instrumental in Alyssa’s growth, development and horse-related achievements that I’ll never be able to fully thank or repay you. You were there for her when I couldn’t be and taught her so many life skills via Bailey that enabled her to become the wonderful goal-directed, compassionate, confident, resilient, determined, and hard working woman that she is. Thank you!

    Alyssa, as you well know, change, transitions and moving on in life all initially take their toll emotionally, but remember – “What doesn’t kill you, makes you stronger” and you are a rock! This year has proved that. Nobody can take away all those special memories or experiences from any of us so relish them and as Jana said, it doesn’t mean they are over forever, just not in your life right now. Those show pics always make me smile and shed happy tears for how happy you were then. Love you, Mom

    • alyssa says:

      Well said, thank you!! It is true, this year has made us all stronger! I will always have these wonderful memories and be grateful for my time with Jana and showing. It has shaped who I am now. It’s amazing what riding teaches, in and outside the ring.

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