Have Yourself a Walking Holiday

Hark! The days are finally getting cooler. I don’t know about the rest of you, but I feel like a whole person again. Yesterday, after doing some work from Downtown Boston, I walked all the way back home in the glow of the late afternoon. Just for the hell of it. And as I approached the north shore of Jamaica Pond, just in time to catch the local muskrat emerging from his nest, tears formed in my eyes. And I’m honestly not sure whether it was the ragweed pollen or the elation of early fall that made me go misty. These next two-to-three months may just be the most glorious time to be outside in New England; it’s a special season when being outside for a long time feels intuitive.

And this fall, I want to encourage each of you to have yourselves a Walking Holiday.

It’s a term and an activity borrowed from our UK neighbors, who’ve been at the heart of the modern resurgence of walking, with their cross-country rambling routes and their social walking groups. And while the most literal definition of “Walking Holiday” is “a holiday that’s built around walking,” the more common interpretation is something that most Americans aren’t familiar with. Lots of us have spent vacations picking off trails in the White Mountains or logging impressive mileage in pedestrian-centric cities like New York or Paris. Then, of course, there’s overnight backpacking and camping. The Walking Holiday is a cousin of backpacking; the fun cousin who introduces you to cannabis, dirt bikes, and house parties that climax at 3AM with everyone standing on the couch, air-drumming the timeless drum solo from Phil Collins’ “In The Air Tonight.”

You stuff some essentials into a backpack—a few sets of clothes, snacks, a first aid kit, and whatever electronics you need to function. You plot a multi-day walk that will take you from Point A to Point B, on trails, sidewalks, quiet roads, you name it. And each day, you refuel at restaurants or markets along the walk, and you retire to local inns for a hot shower and a restorative night’s sleep on an actual mattress that you don’t have to unfurl and inflate. The next morning, you wake up, enjoy a nice leisurely breakfast, and you do it all again. That is a proper Walking Holiday, my dear friends. And after decades of experiencing the grungier side of walking-adjacent travel—the dripping tents, the squashed protein bars, the panicky realization that you may have just wiped your ass with poison ivy—I’ve become a habitual Walking Holiday taker.

So if you’re ready to join the party, here are my three approaches to Holiday-planning.

The Walking Holiday is a concept that took root beyond the U.S., in countries where walkability has been a core component of regional planning more consistently. (The arrival of the automobile pretty much demoted American pedestrians to steerage.) A lot of you are probably familiar with Spain’s Camino de Santiago—a 512-mile walking route through the sun-splashed countryside which leads to the tomb of Saint James, the first martyr of Jesus Christ. This is arguably the most well-known Walking Holiday route in the world. Roughly 400,000 people complete the journey each year. It involves prolonged immersion in the Spanish hills and woodlands, and you spend the nights in a succession of hostels, guest houses, and the occasional fancy hotel. And yet, I feel like walking the Camino is often described in a more solemn and elegiac way. Maybe it’s the pilgrimage connotation, but you’ll routinely hear people explain why they had to walk the Camino after their dog ran away, or after they left a C-Suite position. I don’t think I’ve ever heard anyone say that they walked the Camino because it sounded fun.

Granted, Walking Holiday routes come in varied sizes and committing to walk more than 500 miles could very easily cross the line from “fun” to “flagellation.” But here’s the thing: You don’t have to walk the entirety of an super long Walking Holiday route! In fact, overseas walking ways tend to have enough hotels and eating establishments along the walk that it’s very easy to sample a small piece of a Walking Holiday route over the course of a few days. And if you dig it, you can come back for another round.

I got to experience this last October on a three night trip to Prince Edward Island. (My first visit.) In 2021, local trailmakers created the Island Walk: a 435-mile walking and biking route that encircles the entire island, staying close to the shoreline and passing through charming villages between the birch forests, boglands, and pebbly beaches. Much like the urban trails I’ve written about in Mind The Moss, the PEI Island Walk is a curation of pre-exisiting paths and occasional roadside walks which form a big circle. During my visit, I spent two days on the trail walking 25 miles from St. Andrew to New Zealand. Along the way, I bought a lobster roll from a gas station, I watched hundreds of seagulls take off from St. Peter’s Bay, I drank a beer next to a wetland overlook, and I immersed myself in a thermal pool at a Nordic spa which offered lodging too. It was one of the most decadent 48 hours periods of my life. I can’t wait to go back for more.

But obviously it’s not often that most of us can afford to skip town for an international Walking Holiday. Faced with that limitation, I’ve spent the last few years scouring the Amerian landscape for walking routes that could make for a comparably scenic and indulgent holiday. It’s not easy, given the influence of cars. Identifying a cross-regional walk that’s safe for pedestrians and loaded with outposts for grub and slumber is a tough nut to crack in the U.S. That said, I’ve had some luck lately; two kinds of luck.

We really are living through a renaissance of walking in America and around the world. It’s relatively easy, accessible, and as many of us discovered in the socially-distanced years of the pandemic, mentally restorative. And I think this resurgence helps explain why more long-distance walking routes are starting to take shape. The best example in New England is the Berkshire High Road: the growing footpath that will eventually run from south to north across the spine of the Berkshires, connecting its towns. The first segment of the High Road, which opened in 2021, runs from Pittsfield to Lenox via the Yokun Ridge, on a mixture of footpaths and forgotten roads. It’s a 10 mile walk altogther, beginning from the Bosquet Mountain ski resort and finishing at the Kripalu campus. I’ve traversed the High Road twice—the first time on my own, while reporting for Lonely Planet, and the second time with my dad during peak fall foliage. And both times, I added a few extra miles to the route by starting from downtown Pittsfield and finishing in the heart of Lenox village. (I walked on local roads to connect to the High Road trailheads.) My memories of the High Road are an impressionistic montage of golden leaves, stone cairns, beautifully blackened pizza, and extra crisp hotel sheets.

Hopefully, in the next decade or two, projects like the High Road will become less of a rarity in the U.S. But here’s something else that’s not unusual: rail trails. Americans can’t seem to get enough of rail trails—old railway corridors transformed into paved multi-use paths connecting towns and cities. We’re building them almost as rapidly and prodigiously as craft breweries. And while not all rail trails are ideal for walking, some of them can make for lovely walking holiday routes. Case in point, Vermont’s Lamoille Valley Rail Trail. Running across the northern hills and forests of the Green Mountain State, from St. Johnsbury to Swanton, the “LVRT” is a 93-mile juggernaut with an eastern segment that reminds me of the PEI Island Walk. You could spend a solid three days and nights walking northwest from the St. Johnsbury trailhead to the town of Cambridge, north of Mount Mansfield. Each day would involve around 15-20 miles of walking through wooded corridors and along the Lamoille River itself. And thanks to the layout of the towns and the frequency with which the LVRT visits them, you’d have guaranteed lunch stop each day (such as the great Lost Nation Brewing) and you would spend the three nights in West Danville, Hardwick, and Morrisville.

The only potential hurdle is finding a way to get back to your car from the end of the walk, as public transportation doesn’t really exist up here. If you’re up for walking the LVRT with a friend, you can leave one car in Cambridge and ride over to St. Johnsbury together in the second car. If you’re walking solo, you can make the Walking Holiday an “out-and-back” journey; designating a spot where you turn around and retrace your steps. That might mean simply walking from St. Johnsbury to West Danville and then backtracking the next day, or going all the way to Cambridge and turning the Walking Holiday into a six-day adventure. But when you’re traveling at a slower, more sensuous speed, covering familiar ground can still offer lots of surprises. You could experience soggy, spritzing conditions on Day 1, only to be knocked off your feet by resplendent skies and a more colorful landscape the next morning. You might have missed a little waterfall by the walking route, hidden amid the vegetation, and approaching from the opposite direction could reveal the trickling cascade. A barbecue joint that you strode past might be closed on Tuesdays and open on Wednesdays, with a pork belly burnt ends lunch special. As Werner Herzog said, “The world reveals itself to those who travel on foot.” He would know, having walked across the Alps to propose to his wife.

But if all else fails—if spiriting away to another country, a regional walking way, or a rail trail just isn’t in the cards right now—there’s always the improvised local Walking Holiday. Say you’re tied to New York for the indefinite future. You’ve somehow never made it to Pelham Bay Park, the largest green space in the five boroughs. Brooklyn is home. What would it be like to walk from Prospect Park to the beach at Pelham Bay? How many nights would it take? What other parks could you hit along the way? Where would you eat? Would you stay at hotels each night? Would doing this feel like a holiday…or an ordeal? Wherever you’re based, you can answer that question this fall.

Speaking of really long walks, there’s a cool story in the New York Times by Casey Kelbaugh, a photographer who recently stumbled upon the Long Path. This is a little known trail that leads from Manhattan to the Catskills. It got me thinking about how many “lost” trails are out there; especially trails which are essentially curations of pre-existing walkable spaces, stitched together into one big route. As I’ve learned since starting Boston’s Walking City Trail, it takes a fair amount of work to keep trails like this visible; to update the maps and directions, to replace old trail signs, and to keep people aware that the trail exists. If any of you have bumped into trails that seem to have been forgotten, and you’re interested in exploring them, I’d love to know more!

Oh, and here’s one other idea for a walking holiday. I was up in Toronto the other week, where I linked up with a friend for some TIFF screenings and celebrity sightings (we saw Barry Jenkins!) and a bit of nightlife galivanting (email me for spicy leads!) And during my first visit to Canada’s largest metropolis, I found out that Toronto has the longest designated street in the world. It’s Yonge Street, which runs 34 miles across town. I’d love to spend a weekend traversing the whole thing, powered by poutines.

This story was first published on Mind the Moss.