Trail Ride Evaluation

July 22, 2026
Perryville Road/ PTA Trails
4.01 miles
1h41m

Two weeks after I got Max, I took him for his first trail ride with me. I phrase it that way because it quickly became apparent that this was not his first rodeo. We only did four miles at a walk, but he was totally perfect every step of the way. This was when I finally started to feel excited about my new horse.

One of the convenient things about being at Hannah's is that I'm much closer to just about everybody in the friends group. In fact, Sandy lives just on the other side of the highway, about fifteen minutes away. To make things even better, there are plenty of trail options located between the two barns.

For the first outing, we chose the Pittstown Trails because they're easy and generally quiet. 

Rather than parking at the very public and sometimes chaotic Finn Park, Sandy sent me information for a private farm that allows trailer parking along their driveway for members. The drive is less than ten minutes and I'm very excited to have easy access to this trail system. 

This was my first time trailering Max since bringing him home. He was definitely a little skeptical when he first saw the rig in the driveway, but with some very mild coaxing, he self loaded again. I am pleased to report that these days he hops right on the bus with zero questions.

I beat Sandy there by a few minutes and decided to unload Max and let him get a look around. He backed quietly off the trailer, took a quick look around, realized there was grass to be eaten, and dropped his head to graze. He was clearly unbothered by being somewhere new. 

This also seems to be a character trait of his. He's happy to hang out anywhere there's grass. Good boy.

His body had already improved some from two weeks of turn out and getting shoes on those ouchy front feet. This is what he looked like before 100 miles of walking.

While I tacked up, Max realized that I have snacks in the tack room. Much like Chip, he would like to climb right in there with me. I definitely have to be mindful about keeping the door shut if I'm not supervising. He makes me laugh.

"Hewwo. Got any snackos?"

Sandy arrived and we were mounted shortly after that. Max was starting to get the idea of picking me up at the mounting block, and I've been making a point of hanging out for a minute after climbing aboard. Max is happy to just stand around. An excellent trait. 

Sandy did an excellent job of documenting our first outing.

We began by moseying down the farm driveway to Robin Hill and then along the road. Max plodded happily along on a loose rein while Fina led the way. Right away we saw several things that a green trail horse might be concerned about. 

Someone was riding in the arena at Robin Hill. They were cantering around. Then their horses noticed us and whinnied loudly. Max pricked his ears, but didn't break stride.

Then several deer popped out from various places in the field, including the brush directly in front of us. Max didn't even flinch. 

Finally, we rode along the street. Several cars went by, which was fine. Then a dump truck came flying down the road at speed. Even that was a-ok by Max. That's when I completely relaxed. It's also when I dared to dream of a future that could include many of my favorite things from the past.

Next, we circled the fields, pausing frequently to let the horses graze. I am determined not to rush things with Max. This is a mistake I made in the past. I was always in such a hurry to get places, that I forgot to work on slowing it down. 

Max was delighted that his new job seems to involve a lot of eating. 

Sandy had brought snacks, including fresh blueberries, and we passed them back and forth while we rode. 

That week was also prime wineberry season. This is honestly my favorite thing about the summer, and I was sad to potentially miss it this year. 

We spent plenty of time halting, dismounting, and wading through the berry bushes to pick the ripest fruit. Max was not at all concerned by two middle aged ladies popping in and out of the bushes while they snacked.

Continuing the annual tradition.

Max was doing well and we were having fun so we continued into the woods behind the Grow-a-Row. I had told Sandy we only needed to do a mile for it to count, but Max seemed perfectly content to be moseying about. 

Here, we took turns leading, and I was pleased to see that Max was just as happy out front as he was to follow Fina's lead. 

We also did our first significant hills. Max was surefooted, though he's clearly a little green to terrain. The first time he slid a bit on a slippery slope, he braced his front legs, came to a stop, and calmly awaited further instruction. Good man! He was stumbling a little bit over some of the bigger roots and rocks, but was learning and improving quickly, even on the first ride.

Sandy and I have welcomed so many new horses into the fold together over the years. I was so pleased she was there to do Max's first trail ride.

"Guys, hills are hard."

Leading!

I was a little taken aback by Max's lack of fitness. I knew he'd been out of work and sitting in a stall, but I had forgotten what an unfit horse feels like. I sort of took for granted how much work the girls were in. It felt like second nature at the time.

He just kept chugging along though. He definitely isn't one to complain. I am sensitive to his stoicism and observe him carefully to make sure we don't overdo things. 

That night we went down past the pond, past the warehouses, and then up the hill by the Grow-a-Row. Max took everything in stride. He didn't even spook at the upside down rowboat by the pond, which has historically caused some wide eyes on many other horses.

Lots to look at, but Max didn't care.

A gorgeous night! I do love seeing the golden light playing through his red mane.

The view from the top.

We even checked our first unplanned detour off the list that evening. One of the trails up the forested hillside proved to be a dead end and Sandy led the way back as the crow flies. This involved some bushwhacking and climbing over downed trees. Max asked no questions, even when things got a little thorny. He'll fit right in around here.

By then we were losing daylight so we headed back to the trailers. At this point, Max was starting to offer a nice swingy marching walk. Watching his walk develop over the last month has been pretty crazy! This past weekend, I clocked him walking at over 4mph. 

This proves that the walk all my horses develop is because of training, not because they're gaited. 

Four miles was the perfect distance for a trail evaluation, and Max had passed with flying colors! I was so grateful to Sandy for accompanying us on our first outing. It was the happiest I had felt in a month. 

I honestly think this night was when the tide finally started to turn and I started to get my footing in my new reality. I finally felt ready to embrace the new chapter.

I let Max graze for a bit while the sun finished setting. That's when he came over an initiated a snuggle session. He wrapped his big, thick neck around me and gave me a horsey hug. I rubbed his face as his whiskers tickled my arms and hands. As I inhaled his warm scent, something in my chest softened for the first time in weeks. 

"Don't worry, bud," I told him. "You're here to stay."

The dressage saddle is a little wide for him, but I'm waiting until he fills out a bit more before making any adjustments or doing any shopping.

Buttering up his Aunt Sandy.

We finished the night with our first "trailering in the dark" which was a total non-event. Max seemed relieved to return to Hannah's, and I told him, "Don't worry. I always bring you back. That's how this works." 

I went home that night feeling content. I also felt like this was the beginning of a beautiful friendship