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Horseback Riding at America’s Resort — Our Outdoorsy Adventure at the Greenbrier

September 23, 2019

Postcards from Jiles visiting the Greenbrier Resort

Monday, 23 September 2019

Hello my Equine Friendly Friends!

Today was magnificent! We went horseback riding around America’s Resort. Our “private” trail ride was the perfect way to see the grounds. It’s the first day of fall and it’s as if the trees magically knew it was time to change color. The tree filled Allegheny Mountains are, of course, beautiful to look at and we were also able to soak in the beautiful beautiful grounds, the golf course, the fly fishing stream, the pricey private homes.

It’s been a bit of a joke among some of our Old Town friends that the private homes cost so much money here. “Why on earth would you spend that in West Virginia?” we’ve heard more than once. But this place really is magical!

My horse was way bigger than the other two. Once I surrendered, our trail ride was such a serene and peaceful experience. I can totally see why people get hooked on horseback riding.

I’ve wanted to ride since I was a child. Both of our nieces, Meghan Rose and Miley, are quite accomplished equestrians. And since Miles retired I thought: I could really get into horses now, I’m only 40 why don’t I pick it up, maybe I’ll take up horses as as a hobby. Let me tell you, after experiencing our little trail ride today, this isn’t a hobby — it’s a sport!

Just getting into the saddle alone required strength. I was happy to get on my horse from the platform they have in the ring. My horse, I’d like to point out, again, was way taller than Miles’ horse.

The Greenbrier has trail rides for all levels of riders. We were, of course, beginners. Miles jokes the last time he was on a horse was the pony rides at Bailey’s Cross Roads in 1964. lol.

To ride at the Greenbrier you have to make a reservation. I incorrectly thought that they would shuttle us to the stables. They are actually bringing the horse to you, which is very convenient. They have both 50 minute, and 1 hour and 50 minute rides. We choose a 50 minutes group trail ride. Private rides are also available for an additional fee. We ended up with a private ride since we were the only two people that signed up at that time. We were lucky!

Riding is English Style using English saddles. We’re such Anglophiles, I was excited about that little detail. I guess, I have some Downton Abbey riding fantasy.

You make riding reservations at Kate’s Mountain Adventures which is a meeting place and shoppe located on the lower level of the main hotel’s north entrance. They provide helmets for you there and they must be worn, and you gotta’ sign a waver, and you’ve got to designate an emergency contact person. You can kinda’ see the fear setting in here . . .

Kate’s Mountain Adventures is where you schedule anything outdoorsy. They have a Gun Club with various shooting things. There is also Falconry (which we’ve heard amazing things about from our friend, Steve Forehand — he says it’s one of the neatest experience he’s ever had). There’s off road stuff. As well as the safe and quaint choice of an old fashioned horse drawn carriage ride.

As with everything at the Greenbrier there is a dress code when horseback riding — long pants (jeans or jodhpurs) and closed toe-shoes. Miles wore his jeans but I shopped for this day! This is something I’ve always wanted to do, and I confess part of the reason I’ve always wanted to do it is because of the clothes. I know that’s probably strange, but I’ve loved the look since I was a kid. And Meggy and Miley look so darn cute in their outfits at Horse Shows! So Miles and I ventured out to Dover Saddlery before we ventured up to America’s Resort and I bought myself a pair of jodhpurs. The rest of the stuff I pieced together from my closet. I felt very cool! lol.

All that said, don’t let the outfit fool ya. I was really excited about the ride until we got up next to the horses. I was suddenly aware of how enormous they were. Magnificent. But really really big. I felt this wave of fear come over me but I got on. I’ve been wanting to do this since I was a kid so I was gonna’ do it! And I know I already said this, but my horse was way taller than Miles’.

I felt unsteady at first. Our guide, Ashley, was great! She said because we were beginners she’d hold leads to both our horses. If we all of a sudden felt like we wanted to be on our own she’d let go. I was pretty darn comfortable with her hanging on to us! She also said that if we felt the need to go ahead and hold the saddle. I did hold the saddle . . . . just about the whole time! I liken it to training wheels for a kiddo’s first bicycle.

I asked Ashley, if a person knew what they were doing where would they put their hands. She replied “the reigns” then proceeded to show us the proper way to hold them. I realized how dumb my question was when she replied but she never made me feel stupid. Which is pretty good since the Greenbrier markets to all skill levels.

These horses are magnificent. Miles had Nemo. I rode Traveler. He was a sweet boy and very good a posing for pictures. It’s as though he just knew we had a blog. lol. He was also way way taller than the other two horses (yes, I know I already mentioned that).

Nemo kinda walked by Rockeytop (Ashley’s horse, which she can mount from the ground, btw). Traveler stayed several feet back. I swear that horse knew I was a newbe. And when I finally surrendered and felt comfortable he trotted with me up to the other horses. That’s about the point that I decided I just needed to hold on to the saddle. lol.

Traveler actually trotted with me a few times and I loved it! Ashley taught us that the horses were walking for our ride. Faster than a walk is a trot, then cantor, then gallop.

I had such a wonderful time with these amazing animals. The majority of the time I was having a blissful and serene experience. I will say though that I did feel a wave of panic when I thought I’m going do have to dismount eventually. But I did my best to stay in the moment and not worry about it.

When we got back to the ring, Miles asked “how do we get off the horses?” Ashley said to take both feet out of the stir-ups and let your legs dangle. Then lean forward all the way on the horse. Then kind of hold his mane then swing your right leg along his back. Then come down to the ground onto your left leg while also bringing your right to the ground. Miles went first. I watched him. And as I watched him, I thought: Oh shit! I gotta do this next. And my horse is way taller than his.

I didn’t fall but I didn’t nail the landing. And I was far from graceful. My foot wasn’t flat when I landed. I might have a little limp now. I think I needed to move my right leg faster. I dunno exactly, but I don’t care, today was too much fun! Guess, I’m going to try it again and see if I can get the landing. lol. Ohh, and I swear, Traveler looked at me after I dismounted and was like: yep, I knew you weren’t going to be very good at getting off me!

Okay, here’s are my last few thoughts about our outdoorsy horsey day . . . It is popular opinion that the Greenbrier is haunted (Luis Bujia, my friend and amazing stylist who owns Stylists @ North on Lee Street, told me that before the trip). “Traveler” was also the name of Robert E. Lee’s horse. Miles pointed that out when we were introduced to our horses. He’s so stinkin’ smart! Dorthy Draper, who decorated the Greenbrier with vibrant color and bold fabrics, held fast to the notion that Lee haunted her with a vengence because he didn’t like the way she decorated the place. 

Ok. Now that I’ve scared you, we’re off to take some pictures of what has to be the most instagrammable resort in America!

Pip pip,

xxx – Jennifer & Miles

p.s. The Historic Preservation Fee was included in today’s adventure but, unlike at all the restaurants and spa, the gratuity was not automatically included. Bring cash to tip after or include it on the check prior to your ride.

p.p.s. If you’re not already, be sure to follow our adventures on Instagram! 


This was originally published on our old blog. We decided to bring along some of our favorite old posts to Jet Set Jiles !!! 😘

Bon Voyage, Postcard, Postcards from Jiles, Resorts

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