Appalachian Trail 2025. Flipflop, Pawling to Katahdin, then Pawling to Springer. Days 1-7. Pawling, NY to Great Barrington, MA

Day One. Pawling, NY to Mt Algo shelter, CT . 18.6 miles

Took a bus from my hotel in Poughkeepsie to Pawling, NY. The bus driver was kind and let me off at the Appalachian Trail train station, which is not a typical stop on her route.

The AT train station! My official beginning! I was so excited I felt like crying. Took photos, braced myself while a train flew by a million miles a minute, then began!

Crossed the road, climbed a style, and entered a meadow where my shoes immediately got wet from dew. I didn’t mind, my spirits were sky-high. Saw a deer. Entered woods and accidentally set off my air horn while adjusting my pack. Met my first NOBO right afterward, he came up behind me and thought I had scared away a bear. I told him no, I was just clumsy. He’s a nice fella and we spoke for a while before he naturally outpaced me and went ahead. NOBOs have been hiking serious elevation gain and miles daily for months, so I do not expect to keep pace with them for at least a few weeks. The guy’s trail name is Kenough (“Ken is enough”), and he is in his 60s.

I hiked on my own, enjoying myself and the wooded trail and life itself. My pace was good for someone just starting out, though I quickly felt my lack of elevation gain training this past year. Sure, I have been hiking nonstop, but those trails were mostly flat compared to the AT. The AT is all steep hills/mountains, all the time, up down up down, every day. Took me half a day for my legs to remember they used to hike the Whites all the time, then those climbs began feeling a bit easier. Still, though. I took a lot of gaspy breaks.

There were some really slick wooded bog bridges that slowed me down at times. Fell ass backward off one bog bridge into a stream below. Soaked my butt and the bottom of my pack. Didn’t get hurt, just felt oh so graceful. I later found that my pack liner (trash compactor bag) works well, everything inside stayed dry.

Came across a weird unstable bridge that wanted to throw me into the water since it wobbled precariously with every step, but I managed that one without another fall.

Crossed into CT!

I had only intended to do 10 miles today, since one is only supposed to do 8-10 their first week to let the body adjust, but I felt really good at the ten mile mark, and it was only noon, so I kept going.

Crossed a bridge and looked up to see an unleashed dog running toward me. I shouted “No,” at it, then the owner realized I was there and called back/restrained her dog. Found out she is another flipflopper. Found her info on an AT Facebook page and Messaged her later wishing her a nice hike. Don’t want our future encounters to feel strained since we will likely keep running into each other. Funny, I lost my brand-new baseball cap today and the dog owner later found it. She messaged me saying she would send it ahead with a faster hiker or give it to me herself whenever she caught up. I have no sentimental attachments to that brand-new cap, and I told her she didn’t need to carry it for my sake. With all the tree cover, I don’t find a cap all that useful anyway.

The day warmed up to the lower 80s and was humid, and I sweat like mad nonstop. Made myself stop at every stream crossing to drink a liter of water, often with electrolytes thrown in.

Met a young man named Griffin at a viewpoint. He is out for a multi-day training hike, then he will go home (he is a CT local), take care of some personal things, then begin his own AT flipflop. He will likely start at Harper’s Ferry since he wants a lot of people around him, and the NOBO bubble is around HF right now. I went ahead of him and eventually reached the next campsite, putting me at 15.7 miles for the day. I still felt good though. I sat at a stream, drinking water and refilling my bottles, and talking to a young dayhiker, and Griffin caught up with me. We talked some more, then I decided to push ahead to the next site, about three miles farther. In CT, you have to use established sites, you can’t just camp anywhere.

I went ahead, was fine for the next mile, and then had to drag myself along for the next two. Griffin caught up with me while I was chugging water at another stream, and he was equally tired. We gave each other pep talks – only two or three more climbs, we can do it!! He went on ahead and I slowly dragged myself up and over the climbs.

Finally staggered into Mt Algo Shelter campsite and saw Kenough, who was surprised I had done so many miles (18.6) on my first day. He told me the total elevation gain had been over 3500 feet. I told him I wasn’t planning on doing that many miles every day, at least not just yet.

I set up my tent in a nice spot under some trees. Griffin and Kenough used tents too, no one used the shelter. I prefer tenting for my privacy.

Dipped my head in the clear flowing stream to get the sweat off my scalp, scrubbed myself down with a drop of concentrated soap and filtered water, changed into my sleep/town clothes, wedged my bear canister between fallen logs, and called it an evening.

Took 5mg of CBD to help with bone repair, reducing inflammation, and relaxation. It wasn’t enough, I tossed and turned all night. Will increase my nightly dose to 10mg tomorrow evening.

No ticks on me yet. None that I saw, anyway.

What a great first day! Exhausted, but happy to be here.

Day Two. Mt. Algo Shelter to Cesar Brook Campsite. 14.1 miles, 15.1 if you include the detour into Kent.

Barely slept last night. First-night-itis. Got an early start this morning to make it into Kent when the High Watch Bakery and a cafe opened at 7. Kenough got there before I did, and we were both ten minutes early for opening, so we talked a bit. Got expensive breakfast ($9 for a smoothie). Made sure I got fruit and protein. Also had an egg and cheese sandwich. Griffin showed up, and he ordered too. After that, I bought a bit of resupply at the nearby gas station, then it was back to the trail!

Kenough zoomed ahead, I probably won’t see him again as he staying in a campsite beyond me tonight. Griffin and I hiked most of the trail together. He is a nice young man the same age as my older daughter.

The trail! Up down up down up down. Lots of elevation gain. Went 14.1 trail miles which, again, was too much for my first week. Felt like I was in survival mode for the last two miles. I will cut my mileage to 10 for the next few days, and I’ll take a zero in Great Barrington. I think one zero a week for the first month might be a good idea to lessen the chance of overuse injury.

It was hot and humid, upper 80s. Another day of sweating like mad and chugging electrolytes.

Some of the terrain today reminded me of the Whites. Some steep bits straight down with boulders/rocks/roots.

Bugs were out and a pain, but not so bad that I needed a headnet.

Met another NOBO. Half Stick passed us and camped at the same location. Nice fella.

Cesar Brook Campsite had lovely almost-flat spots under the trees. Did all my chores, took 10mg of CBD, and had a very relaxing evening. I think 10mg is the way to go out here. Better than ibuprofen.

Will definitely keep my mileage around ten for the next couple of days. Gotta pace myself better and ease into things. I need this body to last not just for this thruhike, but for the many others that will follow.

Day Three. Cesar’s Brook Campground to Belter’s Campground. 8.8 miles

I got a good night’s sleep, seven hours straight.

Packed up and left. The last two days had been super hot, and my body felt dehydrated. I reminded myself that I am not doing an intense few days, I’m doing an intense few months, so I need to pace myself. I therefore made today an 8.8 day and took it easy.

It was much cooler, which helped, but I stopped a lot anyway on the steeps, and I drank a lot of water.

Hiked by myself all day since I left before Griffin awoke. Didn’t see any other hikers on trail.

Got to Belter’s Campground which is on a little hill up on a ridge. Lounged in my tent. A couple of ticks crawled on top of it. Glad I haven’t found any on me yet. Treating one’s clothes with permethrin is important, glad I did that before I began this hike.

Griffin rolled into camp a little later, and I was glad to have the chance to say goodbye since he gets off trail tomorrow.

Day Four

14.7 miles, 16.5 if you include breakfast and grocery detours. Belter’s Campsite to Riga Shelter

Got another good night’s sleep. Woke feeling refreshed.

Packed up my tent and hiked about a mile and a half down the trail and on a short side path to the Mountainside Cafe for breakfast. The cashier told me, “You’re welcome to dine here, but you have to leave your pack outside.” I ordered my overpriced $20 spinach omelet to go and ate it outside on the tiny porch. Someone got their pack stolen on the Ice Age Trail last year, so no, I will not leave my pack outside unattended.

Went back to the trail and ran into Griffin. He and I tackled the first steep climb of the day together, then we got a selfie by Amesville Falls. After that I got ahead of him for a bit (slightly faster pace) and spent much of the day on my own.

The trail felt mellow. The ups were mild, and there was a light rain that kept the heat and the mosquitoes away. Passed a gorgeous meadow scene. Also passed Giant’s Thumb, a glacial erratic on top of Raccoon Hill.

Made it to Salisbury and walked off trail to a grocery store for resupply. Passed a No Kings Protest, which was wonderful. Tons of signs and people chanting and cars honking. THAT is the country I know and love.

Came out of the grocery store, and there was Griffin! We talked for a bit one last time, then we walked back to the protest together. He stayed there and waited for his ride while I went back to trail and hiked another 3.7 miles up to camp. I enjoyed Griffin’s company and hope to see him again at some point, though it may be months from now, after we have both flipped and are heading SOBO.

A lady in a van gave me an apple at the beginning of my final climb. My first Trail Magic! Those final 3.7 miles were mostly up up up, but it didn’t feel that bad. The temperature not being a million degrees helped.

Met a Russian woman named Helena a couple miles from the shelter. She started at Pawling a couple days before I did.

Stayed at the Riga Shelter area. Beautiful view from the shelter, and the shelter itself looked new. I prefer tent camping, so I set up not far from the shelter. A group of four college kids and a local couple arrived later. I slept very well. The 10mg of CBD each night really does the trick. Also, the night was cool and breezy, which is perfect camping weather.

Tomorrow I cross into Massachusetts.

Day Five. 9.6 miles. Riga Shelter (CT) to Glen Brook shelter (MA)

I had a wonderful sleep last night.

Shared the tenting area with a group of young adults and a couple. Everyone was quiet and respectful.

Started the day with a climb up Bear Mountain, Connecticut’s highest mountain. Mount Frissell is the highest peak in CT, but most of that mountain is in MA. All of Bear is in Connecticut. The climb felt like a slog, but the peak was pretty.

Soon after descending Bear, I crossed into Massachusetts and entered Sage’s Ravine. The ravine walls were beautiful, and the trail followed a flowing stream. Lots of mossy boulders. Breathtaking. Really liked this stretch.

First climb of MA was Mt. Race, which I greatly enjoyed. Nice open ledges and beautiful views. Went down that, then came straight up Mount Everett in a steep and White-Mountainy way. Even had some wooden steps attached to bare rock. The summit of Everett was meh. Nothing like the gorgeous Mt. Race.

Was really tired at this point. Made it to Glen Brook Shelter at three, creatively pitched my trekking pole tent on a wooden platform, and settled in for the evening.

As I was texting my daughter, I looked up and saw a bear walk by my tent. I spoke out loud, hoping to startle it, but it calmly looked at me as if to say, “What?” and then continued on its way. It showed no interest in my bear canister. Glad I use odor-proof bags.

Day Six. Glen Brook Shelter to US Route 7 MA. Around 8 miles.

Didn’t sleep well. Tossed and turned wondering if the bear was gonna walk by again. To my knowledge, it didn’t.

Met Mark, a Harpers Ferry Flipflopper, while eating breakfast at the picnic table. Nice guy. He went ahead while I finished packing up.

Took my time today. The trail was mostly downhill, though there were some short and steep climbs here and there.

Beautiful mountain laurel all over the place.

Realized a few miles into the day that I left my knee brace at the campsite. Shoot. Will have to buy a new one in town. I am not climbing for miles back up to get it. Left a note on FarOut, hopefully another hiker can use it.

Made it down one final steep bit and walked through a flat and swampy boardwalk area – lots of mosquitos here! – then went through some nice open woods, past a Shay’s Rebellion battle site, and finally to a road where there was a trail magic sign!

I followed the sign and reached a wonderful picnic spot where a couple of church groups provide burgers, hot dogs, fruit, iced tea, and many kinds of snacks to hikers. All under a large shaded tent with lots of folding chairs. They’ve been doing this for eight years, but it’s their first day of the season. I ate a veggie burger and asked if I could make a donation, but they said they couldn’t accept it.

Mark was there. He, the volunteers, and I chatted for a while. When I was ready to leave, one of the volunteers offered to drive me into Great Barrington to my motel. I gratefully accepted and walked the AT to the next road crossing where the volunteer met me and drove me to town.

Great Barrington is fantastic! Very hiker-friendly. The Quality Inn folks let me check in early. The shower felt so good! Did laundry two blocks away and the locals chatted me up. Bought a new knee brace at the nearby CVS. Ordered local delivery of stuffed shells and a salad.

Now all my things and I are clean, I am full of food, and I look forward to a day of laying around and doing nothing. Will probably check out a local shop that sells veggie/fruit protein shakes at some point.

Day 7. Rest day in Great Barrington.