Hiking Trails Near You: Sheppard Point


Winter may be trying to make a comeback, but that won’t stop me from planning out some seriously great hikes once Spring has finally sprung.

If you’ve got the hiking bug like I do, then you’re in luck! I’ll be featuring each trail I go on in our newsletter, letting you know the ups, the downs, the tricky spots, and the spots you won’t want to miss.

Ready for our first trail?

This one sticks close to home. Located right in Trail of Tears, Sheppard Point is a can’t-miss if you’re looking for a fairly short, but pretty challenging, hike.


If you’re new to Trail of Tears, then navigating the area can be a little confusing. Luckily, Sheppard Point is one of the easier trails to get to.

From the front entrance, just stay on the main road. Pass by the nature center (it’ll be to your left) and continue down the main road. In another mile or two you’ll see the head of the trail to your right.

Check out the video below to get a visual:

Trail Rating

Difficulty: Challenging

Compared to some of the other trails at TOT, this one is definitely a difficult one. The trail is mostly dirt
or gravel based, and it’s a serious uphill battle to get to the lookout point—my Garmin claimed I had climbed 70 flights of stairs by the time it was all said and done.

You’ll also have to climb down some rocky stairs and scale a few downed trees as you hike, but it’s all worth it once you come up on that view of the Mighty Mississippi!

Keep in mind: This trail is about 3 miles (though my tracker clocked it at a little closer to 4). The part that once made it loop into a full circle has been closed off to the public, so it’s become more of “walk there, then walk back” type of trail. That said, it’s still a fantastic workout.

Distance/Time: 3-4 miles overall.

It usually takes me about an hour to an hour-and-a-half to finish. I like to keep a brisk pace when I hike, so if you’re the type that likes to slow things down, then it may take you a bit longer. Time also varies depending on how long you linger at the overlooks.

Kid Friendly? Depends.

I’ve seen kids of all ages on the trail, but many of them don’t end up making it to the end. There’s a stopping point about a mile and a half in that seems to be the common turnaround point. The type of ki that seems to have a boundless amount of energy would probably do well on this trail though.

Dog Friendly? For the most part.

I’ve seen everything from Miniature Dachshunds to German Shepherds on this trail, though I can’t imagine how some of those smaller dogs make it after the halfway point. Rule of thumb seems to be that if your dog is obedient and good on a leash, then have them tag along.

Handicap Accessible? Sadly, no.

Tricky Spots

There are plenty of treacherous little spots throughout the trail, but with some good shoes and some game planning you’ll be able to get past them.

Here are a few tips:

– BRING WATER! Especially if it’s hot outside. This seems like a pretty obvious rule of thumb, but, trust me, this trail is a bear when you forget it…

– Take it slow at the beginning of the trail. As soon as you cross the bridge at the head of the trail you’ll starting a winding path up a massive hill. You may be tempted to run up it to just get it over with, but you’ll want to conserve some of that energy for the second half of the hike!

– After that first hill the trail tames down a bit, but things will pick back up at the midpoint (pictured to the right.)

– The second half involves some downhill scaling of rocks—like the picture below. Make sure you have good footing here because the loose rocks can cause a few problems for your shoes grip-wise, especially when you’re near steep drop-offs.

– Once you make it down the rocky part of the trail, you’ve got one more tiny mountain to scale before you reach the overlooks that sit at the top. No fears, this one is pretty similar to the one at the beginning of Sheppard Point.

On the bright side, once you reach the top it’s all downhill from there—literally!

Points of Interest

You know I always save the best for last!
I’m a sucker for a good overlook and this trail has one of the best—except for one particular favorite of mine on the PeeWah Trail, but I’ll tell you more about that one next time.

The way the rocks jut out over the train tracks below, watching the barges slowly make their way down the Mississippi…there’s nothing like it.

Hiking with someone special? Hit the trail later in the evening and you’ll be treated with an amazing view of the sunset over the river (talk about a romantic view!
I know it may be hard to picture since the trees are still a little bare—and because the weather last week was overcast, making my pictures pretty lackluster—but the way this trail ends completely makes up for the rough journey you had to take to get there.
Curious about some of the other trails in our area?

Stayed tuned in the coming weeks for more trail reviews!



Kelly Crites

Admin for our Cape studio and the face behind our blogs, Kelly is a year into her new, healthier lifestyle and ready to share the tips and tricks she learns along the way. Current Goal: Making it through an entire Tough Mudder.

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