After a series of challenges, a satisfying time in the mountains and towns of central Vermont.

How It Began

Two years ago, Mark, Andrew, and I hiked the northern third of Vermont’s 272-mile Long Trail, the oldest continuous footpath in the United States running the length of Vermont from Canada to Massachusetts. The plan for this July was to hike the rest of the trail going southbound over a couple weeks. We had a nifty plan to take trains up from Washington, D.C. to start and end the trail to avoid leaving cars unattended in Vermont. Then, well, life happened.

First, Mark wasn’t able to make the trip. We would miss his company. Second, at 10:00 p.m. the night before Andrew and I planned to catch the Amtrak Vermonter north out of Washington’s Union Station, we got notifications that our train was flat out canceled (track issues? who knows!). Hotels had been booked and resupply packages had been sent, so we had little leeway on a delayed start date. Plan B: rent a car one-way out of BWI. After the drive — a huge thank you to to Andrew for doing all the work — we settled into a wonderful night of drinking and eating in Waterbury, the first of our awesome small towns in Vermont. We went to bed in the lovely Old Stagecoach Inn with dreams of many trail miles before us. The next morning, my Montpelier-based brother Cory and family picked us up from the local Enterprise we returned the BWI rental to and dropped us off on the Long Trail on the Winooski River — right where they picked us up at the end of our southbound hike down from the Canadian border in 2022. (Funny story, if you’ve ever wondered about dropping rental cars off one way: within minutes of us driving up with the car, an Enterprise employee wiped down the dashboard and handed the keys to a customer who had been waiting around as we drove up.)

Day one for us was always destined to be a challenge. Starting at the Winooski River put us at the lowest elevation of the entire Long Trail, only a few hundred feet above sea level. The trail immediately takes us up a 4,000 foot vertical ascent from the river to the top of Camel’s Hump, one of Vermont’s highest and most iconic mountains. With a 10:00 a.m. start, it was hot, humid, and our packs at their heaviest with four days of food and libations. Andrew took off at a gallop. I knew I wouldn’t be able to keep up. Though this terrain was very familiar to me after hiking 30 of the 46 nearby Adirondack High Peaks since our previous Long Trail outing, I had gotten used to a rather slow personal pace when going uphill on rocks and roots. I messaged Andrew that I was fine but a turtle. He shouldn’t wait for me. The plan for the day was 16 miles even after a late start and I was prepared to hike until evening if need be to catch up.

Dripping with sweat, I made my methodic way up Camel’s Hump. Near the top, I encountered the most shocking hiker I had ever crossed path with us on any trail, any where. A 60s-ish man, grinning, had a pistol open-carried on his hip and a bright yellow shirt with the words BLACK LIES MATTER written in bold font across it. So as to make sure nobody could unthinkably miss his shirt and gun message, he was making racist jokes to other hikers. I was shook with this near-KKK level of public intimidation. I chatted with one of the Vermont state forest caretakers at the top, who was also stressed but similarly at a loss for what could be done. We resolved to stay silent, thinking the gunslinger probably wanted to start a provocation with his getup. Eventually he left. In other news, the caretaker passed a message to me that Andrew had waited for more than an hour and then opted to push on to the next shelter. At least it was a perfect day at the top of Camel’s Hump, with a light breeze and clear visibility. I took it all in and carried on.

I rolled into the shelter, Montclair Glen Lodge, around 6:00 p.m. Andrew had set up for the night, even though we had plans to hike another five miles to the next shelter area. Even though I was feeling pretty decent after taking the day easy, we thought why not, we could make the miles up later. Andrew, oddly, mentioned for the first time not feeling very good. We agreed he was most likely dehydrated from the warm day. As the night went on and we made dinner by our scenic log cabin abode, Andrew took a few bites but then just stared at his food. He was feeing worse. After another hour or two, another couple hikers joined us, a duo from Belgium who had also started southbound that morning from the Winooski. They had been traveling the United States by van and foot for almost six months and opted to conclude their U.S. sabbatical with the Long Trail. Andrew went to bed early to sleep off his malaise. Eventually, the Belgians and I joined him in the lodge for the evening.

Andrew had a terrible night and in the morning was not in any condition to continue. After talking it out, Andrew decided to take a popular day-hiker side trail and head back toward Waterbury. I would continue on and hope he could recover enough to rejoin me down the trail. I pushed on, worried and doubting my decision to leave him. It was already hot and muggy even early and I knew both of us had another tough day ahead of us. After a few hours, Andrew stopped texting regularly and both myself and his wife, following along from Virginia, began to get increasingly concerned. Worst case scenarios started to go through my mind. For the first time in my hiking years, I called the emergency 911 ranger number and gave information on where Andrew was supposed to be. I kept picturing him passed out from severe dehydration. Blessedly, Andrew made contact before I had even hung up with the rangers. He had made it out to a road, though still weak. My brother Cory and spouse Gus made another save-the-day pickup to get Andrew back to town and a room. I made the absolute wrong decision to separate from him that morning, even though things worked out in the end. I spell this out as a teaching moment I hope never to need reminding of again.

The next challenge came courtesy of mother nature. Hurricane Beryl tropical storm remnants were due to strike Vermont soon, threatening to dump historic levels of rain, along with high winds, thunder, and lightning. I tried to do my best weather forecasting to guess when it would get to me in the mountains. I figured it would be best to be up high in a solid man-made structure instead of risking a flash flood and the integrity of my trekking-pole tent down lower. After a slow-going but beautiful day on the trail, I ended my evening at a ski hut (Stark’s Nest) at the summit of the Mad River Glen ski resort, one of the legendary badass ski locations of Vermont. A fellow hiker, northbound on the Long Trail, who happened to be from Baltimore joined me for the evening. He and I enjoyed outstanding views on both sides of the ridge, including a sunset over Lake Champlain and the Adirondacks.

The next day is where the guessing got interesting. I knew the storm was going to hit. I just didn’t know when. I decided to do something uncharacteristic for our style of hiking and do only about five more miles for the day in order to stop at the next mountaintop ski hut when it started to rain. This one, decidedly older and more dilapidated than my previous night’s stay, was at Sugarbush resort near an older ski lift called Castle Rock. I made myself at home, took out the paperback book I had decided last minute to toss into my gear, and settled in to experience the rain, wind, trees, and post-apocalyptic feel of an older ski resort in summer. (Reading note: my book choice was Cormac McCarthy’s The Crossing, a desperate, grim, lonely western that’s part of his border trilogy. Atmospherically, it was perfect.)

Later in the afternoon I heard from Andrew. He was not going to recover enough to continue on the trail. Our flexible return travel plan made it relatively easy to split from each other but it was still a bummer. After reflecting on it all, I made the decision that I didn’t care that much to finish the Long Trail as we originally planned and would just do the first week of our itinerary with a more leisurely daily mileage pace. With luck, the three of us could reassemble in the future and pick it back up again. Travel cancellations, sickness, and elemental challenges colluded to change the make up of the adventure. But the adventure, for me, continued.

I marveled all night at the power of nature as pummeling wind, thunderous blasts of lightning, and torrential rain swallowed me at Castle Rock. Like the hero in a fantasy or war novel who choose his sanctuary well, I survived the night. Others in Vermont were not so lucky.

May the Road Rise to Meet You

The next morning, it was still windy and rainy.

I carried on over Vermont’s Presidential Range, up Lincoln Peak and Mt. Abraham (and then Grant, Cleveland, Roosevelt and Wilson) before camping for the night at Emily Proctor Shelter. You see, the Long Trail is resplendent with shelter and lodge options, some of which have tent space, others don’t. As I was trying to pick where to stay this evening, I was trying to avoid ending up at the same area as a large group of 12ish year old boys on some kind of camp outing. I knew about this group thanks to the now numerous northbound Long Trail hikers who passed by me and gave scouting reports (pun intended). I succeeded and spent a really great night with two older gentlemen hikers. Their only flaw was NOT joining me in my whiskey, which I was trying to finish before restocking when I got to town the next day. Their failure to assist ended up in me consuming more than I needed. In turn this begat some night time stumbles to pee and a groggy head in the morning. How I am to bring joy as the Whiskey Fairy if others don’t partake?

After slowing down a few nights in a row, I realized that I didn’t quite have enough food (and now whiskey) on me to finish my elongated first/final week. When I hit the road crossing at Middlebury Gap, instead of toughing it out with stretched rations I decided to grab a bonus night in town in Rochester, Vermont. And gosh did this hit the spot. The awesome proprietors of the Stable Inn picked me up and dropped me off from the Long Trail parking lot.

I enjoyed a farmers’ market, lovely long lunch, and Tolkien-inspired bookstore in town, and I had an absolute blast drinking and eating with locals all evening at Doc’s Tavern. I even got to swim and wash up in the pristine river that flows through Rochester. In Vermont, come for the trail and stay for the towns. No, really, I spent a fair bit of time musing about moving here. I think I can convince Cheryl.

When I got dropped back off at Middlebury Gap I spotted the Belgian couple I had last seen the night Andrew got sick. Though it would chronologically occur later in the hike, I helped to bestow their trail names Tomorrow and Slip n’ Slide. (Side Note on Trail Names: many folks on the trail not only go by a trail name moniker, many of them ONLY go by this trail name, i.e. “Hi, I’m Evan . . . Hey, I’m Legs. . . . Right, I’m Whiskey Fairy.” This means you need one even if isn’t necessarily your thru-hike jam.) The Belgians and I would end up not only spending the rest of the week together at shelters but they even took the second room I had already paid for at the Inn at the Long Trail when I thought it would be Andrew, Mark, and I would be crashing there. The trail serendipitously provides, at least for them.

The hiking was becoming much easier after crossing Brandon Gap, which I had heard in advance from northbound hikers. Word was the rocks, roots, and steep ups and downs of the northern Long Trail smoothed out for much of the remainder of the trail to Massachusetts. This was a common talking point as north and southbounders passed each other on the trail. I would always perk up and tell hikers going the other way that even though it was slower going as they made their way north, it came with bigger views and far more interesting terrain. In fact, the spruce, balsam fir, birch, and fern understory woods of the higher ridges was probably the most beloved feature of the entire trail for me. This forest is truly magical and literally fragrant.

I had picked up another bottle of whiskey in Rochester and was eager to share it before I got off the trail. The next night provided a perfect opportunity. Not only did we stay at one of the newest and nicest shelters on the trail, Sunrise Shelter, but the collection of hikers for the evening included a young kid, Crane, finishing the trail the next morning before heading to UVM to begin his Ph.D. When I offered whiskey he thought he had died and gone to trail magic heaven. When I offered a cigar he swooned with joy. Several others partook, from a man in his later years from Maine, a Canadian engineer from Montreal, and, as mentioned, the Belgians Tomorrow and Slip n’ Slide. The Whiskey Fairy had finally risen to the moment.

I paced out these final two days on the trail, since it was the end of this segment for me. This allowed for more reflection, breaks, and time to chat with fellow hikers. I’ll admit that it was at times tough for me to slow down since we’re used to higher mileage days, but it ended up feeling right. The final night at Rolston Rest Shelter was bittersweet as I got to know more Long Trail thru-hikers and then bid them happy trails the next morning.

The Long Trail joins the Appalachian Trail (AT) at Maine Junction. From there, the AT northbound breaks off toward New Hampshire and southbound shares the same path as the Long Trail for 100 miles. These miles will now wait for another trip, either an AT thru-hike (hey, a kid can dream) or maybe a future leaf-peeping autumn outing.

Our original trio had circled the Inn at the Long Trail from the beginning as a key resupply and stop to enjoy ourselves. It would now serve as my final night in Vermont. Boy, did it exceed even lofty expectations, from a perfect pub pint of Guinness to quirky cabin decor to splendid breakfast. And as a stop on the Long Trail and AT, it was full of hikers and their stories. The trail and its welcoming community are unbeatable and unforgettable. Can’t wait to be back.

It was especially easy to return home from the Inn at the Long Trail and Rutland, Vermont. A free bus picked me up and a finally useful Amtrak got me back to DC. Andrew, it turned out, had a few extra travel headaches and adventures getting himself back a few days before, but that is his tale to tell.