Jenny the Trailhead

Jenny the Trailhead Your Midwest outdoor guide to road-tripping, camping, backpacking & hiking!

Max Patch made us decide we’re gonna go ahead and do the Smokys next year.
05/03/2026

Max Patch made us decide we’re gonna go ahead and do the Smokys next year.

Me & Ziplock’s 32 mile, 2 day hike from Massie Gap/backpacker’s parking to Damascus. We cut a 3.5 day hike down to 2 day...
05/01/2026

Me & Ziplock’s 32 mile, 2 day hike from Massie Gap/backpacker’s parking to Damascus. We cut a 3.5 day hike down to 2 days so we could get back to RoadRash, who was recovering in town from being really sick on trail during our first section in Tennessee.

We got to see some ponies, but after that we pushed through 2 very warm, unshaded but gorgeous, LONG days. Not only that, this section was mostly a detour. What better for a FarOut App scout to do than report on this reroute! We were technically on the old Appalachian Trail, blue blazing on the Mt. Rogers trail and yellow blazing on the Iron Mountain multi-use trail until we reconnected on the AT for the last 3.5 miles into town.

The Virginia Creeper trail and the AT were severely damaged by Hurricane Helene. The destruction in this area was wild to see. Tons of downed trees. (I’ll share in another post some of those photos.) A lot of Northbound hikers opted to road walk or shuttle past the closure and skip the reroute. We went through it. It wasn’t awful but it definitely wasn’t the well maintained, bear box having, plenty of tent sites at the shelter AT.

For the foreseeable future - if you’re planning a section hike through Grayson, just know you won’t be on the Appalachian Trail from Grassy Ridge Rd. to Straight Branch parking area. It’s approximately 22.8 miles of rerouted trail.

Some of my favorite flower pictures from our section hikes this past week thru Tennessee and Virginia. Springtime is so ...
05/01/2026

Some of my favorite flower pictures from our section hikes this past week thru Tennessee and Virginia. Springtime is so beautiful on the AT.

Ok but, how else do you get out of your tent when you’re over 40?? 👀 The countdown continues! Only FIFTY…50 days out fro...
03/03/2026

Ok but, how else do you get out of your tent when you’re over 40?? 👀

The countdown continues! Only FIFTY…50 days out from connecting some sections in Tennessee and Virginia. We did some leapfrogging around in 2022 so we’re finally picking those pieces up! Then we’re reuniting with Zippy for the following week! I’m starting to get into buckle down (stretchin’ & walkin’) and list mode. Food, gear, clothing. I swear I’m not panic buying anything this season bc my gear I carried was perfect last year!

(Well, actually I do need a new stove. Ask me how I got my trail name 😂 maybe I’ll put that in my stories)

Back on the AT in 67 days (si###x sevennnn)Reuniting with RoadRash and Zippy so soon. Can’t wait for the 5am wake ups, t...
02/16/2026

Back on the AT in 67 days (si###x sevennnn)
Reuniting with RoadRash and Zippy so soon. Can’t wait for the 5am wake ups, the 6am start times, the sunrise peeking through at us as if to ask “Why are you already hiking?!”, the “at camp too early” shelter naps, the sharing of food were burnt out on, the daydreaming of fountain soda & cheeseburgers, the 5 minute long Zip jokes to take our mind off walking for a sec, the inevitable rainy days where we embrace it, the views, the experience, the disconnecting from everything but the ground beneath us.
We are connecting LOTS of dots this year and closing in on having all of Virginia done in a couple seasons!

2016. The year I started hiking & backpacking. The year I did the first big hike (Mt. LeConte ❤️) that gave me the high ...
02/06/2026

2016. The year I started hiking & backpacking. The year I did the first big hike (Mt. LeConte ❤️) that gave me the high I have always been chasing. The year I did my first solo camp. The year we bought an old utility van and turned it into a makeshift camper. The year I finally found where I fit. My true passion in life gifted to me at the age of 31.

What a wild and wonderful 10 years it’s been. Just since I have begun in 2016, I’ve backpacked and traveled all over the US, adding 20+ National Parks to the roster. Done several hundred miles on the AT. This journey has taken me down many roads I never imagined. A little community online (I ran a busy blog that gained some traction for a handful of years, but I ADHD burnt out on it. Maybe I should get back to it!) I built this Instagram account from the floor up and garnered 12k+ friends and followers. I’ve worked with some of my favorite BIG and small brands & outdoor companies. I’ve volunteered for trail orgs and non-profits and even created outdoor volunteer opportunities in my community. I was a backpacking guide and the co-owner of a beautiful outdoor expedition company where I got to experience incredible places and meet some great people, including one of my best friends. I’ve been featured in Backpacker Magazine, Terrain Magazine, invited to speak at outdoor expos and on podcasts. Every single thing - I’m proud of and grateful for.

And I didn’t really even DO anything, except be super psyched about something I love so much. Life is weird and short and you should GO DO WHAT YOU LOVE. Yell about it! Be excited about it!

Imposter syndrome who? I’m not afraid to be proud of these achievements and casually dismiss it anymore. It’s freaking cool as hell, and after a break in 2025 I am really excited to be back this year on your feed - in the woods and on the trail. I’m doing a bunch of miles on the AT this season and I’m bringing with me. Let’s gooooo.

True North Expeditions, Inc.
02/19/2024

True North Expeditions, Inc.

All of our upcoming backpacking, yoga, hiking, kayaking, canoeing, camping, and first aid courses can be found here. Do you want us to plan and host a specific event in your area? Let us know!

Oh, River to River. A love/hate. It tests your patience, your will to live and the tread on your shoes. Saturday we hit ...
02/13/2024

Oh, River to River. A love/hate. It tests your patience, your will to live and the tread on your shoes. Saturday we hit mile 100 on the trail, and by the end of yesterday we have only 37 left to go before we complete all 151-ish miles.
Well, according to the signs it’s 151. According to the Internet it’s 160. Idk if anyone really knows 🤷🏼‍♀️ that’s the thing about this trail. You never can bank what your day/weekend is going to be like because every resource has a different number, so you just hope for the best and if you do 8 miles when you thought it was 5 or 18 when you thought it was 13….its whatever.
Mud, thorn vine whips to the face, tripping on gravel roads, many sus creek crossings…I miss it already. (Maybe it was the slack packing and Giant City cabins this trip that’s making me miss it 🤔) Ready to wrap this thing up!

Some highlights from our weekend; pictured and not pictured. - Ferne Clyffe to Hilltop Campground (12mi) Friday morning ...
02/13/2024

Some highlights from our weekend; pictured and not pictured.
- Ferne Clyffe to Hilltop Campground (12mi) Friday morning about 2.5? miles in to our day we saw a HUGE bobcat that crossed the trail right in front of us. We both just watched. Sad for no pic but I’m glad to have witnessed it! A little natural bridge. So. Much. Roadwalking. It was about mid-60s temp wise. We self shuttled so we hiked back to my truck and checked into the lodge.
- Saturday (Hilltop Campground to Rocky Comfort Rd - 10.5 miles) first half of the day was all road. We got to Panther’s Den and heard “So, you come here often?” For the first time ever on a trail. No, sir. Also saw an abandoned stroller and an old car that was flipped and rusted out.
- Sunday we hiked from Rocky Comfort Rd to Giant City Lodge (7mi). We passed the old SIU fireplace. We added a little extra mileage bc we turned around to explore the Hidatsa Indian Earth Lodge. Finally hiking into Giant City was a massive milestone for us. Grateful for a warm shower at night, a spider on my pillow (NOT) and a bed this trip.

I loved this section honestly. It feels so different on the west side of the state. An abundance of water sources too.

Another grand AT adventure in the books with a memorable crew. ❤️Heading out Friday for the Missouri beginners backpacki...
10/05/2023

Another grand AT adventure in the books with a memorable crew. ❤️Heading out Friday for the Missouri beginners backpacking bootcamp trip I lead every year. I love backpacking season!!

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