Late last year I very quietly rolled out paid subscriptions for Pinch of Dirt. Originally, I did it because I wanted to put past posts behind a paywall, to increase the illusion of privacy and ephemerality of these digital letters. But as generous friends and family friends and family members began to sign up—to support my writing and me—I realized two things: First, that I would love if this newsletter could provide more financial stability in an unpredictable profession. And second, that I needed more of an incentive for strangers who don’t know me from Eve to generously support my writing.

What I’ve arrived at is something I’m calling itineraries, and here’s how it will work:

1. Paid subscribers can send me a brief note about an upcoming trip or destination. Tell me a little bit about what you hope to do there: Do you want to know the best gardens to visit in southern Italy, or the best day hikes in Los Angeles, or the best backpacking trips accessible by public transportation from New York City? (Incidentally, I wrote about one of those here.) Are you hoping for an easy/beginner backpacking trip, or a tough all-day urban trek, or even the best park in a new city to sit and write or draw for the afternoon?

   Let me know: How much time you have; whether you have a car or can rent one; what your fitness level is and how challenging you want the activities to be; and any other important details. Since we’re still in the midst of a pandemic, these requests can also be about outdoorsy/nature things to do where you live now, but with the caveat that for locals my recommendations might end up seeming so obvious, and I’ll risk recommending things you’ve done one thousand times before. Then again, maybe not!

2. I do the kind of research I might do for my own vacation or trip. Lots of internet searches, basically.

   I’ve done this to plan challenging day hikes in Hong Kong; to find somewhere to go for my first ever trail run in California wine country before hitting the vineyards; and to select a Christmas Eve hike that everyone in my family—from my 16-year-old brother to my 70-year-old dad—enjoyed (even if it did end up being two miles longer than expected because of winter parking lot closures).

3. I prepare a sample itinerary. The form this will take could vary from destination to destination, but I’ll probably take inspiration from The New York Times “36 Hours” column and Backpacker’s “Trips.” Whenever I can supplement with first-hand experience, I will.

   What I find might not be the perfect fit—they’re just suggestions, after all—but hopefully something clicks for you; in a perfect world I unearth something you never would have thought of! And since these will go out to all paid subscribers, others will hopefully find them interesting and useful as well. The goal is to inspire and inform!

I’ll be publishing these on the first of the month to start; the first few will go out to everyone, but eventually they’ll just be for paid subscribers. So please, subscribers, send me your trip queries!

Below I’ve shared a backpacking itinerary near New York City based on a past trip of mine. An email that might prompt such an itinerary would be:

I live in New York City and am an enthusiastic hiker/backpacker. I’m looking for a challenging trip for a three-day weekend for me and a few friends, also very fit/athletic. One of them has a car we can use. We like views and bagging peaks, and aren’t afraid of a little discomfort!

Catskills, New York: Devil's Path

Some people say the Devil’s Path is the most dangerous trail in the northeast, others just say it’s among the most challenging trails. Suffice to say, it leads Backpacker magazine’s list of the 12 toughest trails in the U.S. In short, it’s a classic, and for a fit, outdoorsy New Yorker, a must-do.

The Devil’s Path crosses the mountain range of the same name. Over almost 24.5 miles—closer to 26 miles including side trails to shelters and viewpoints—you’ll gain (and lose) more than 8,000 feet of cumulative elevation. The trail goes over five of the 35 Catskill High Peaks over 3,500 feet. (Two more are accessible via side trails, for anyone eyeing the 3500 Club.)

As president emeritus of the Catskill Center Sherret Chase writes, the Catskills aren’t “proper mountains in the geologic sense,” but rather an uplifted sedimentary plateau, carved out by erosion. The sedimentary rocks—shales, sandstones, and a cap of conglomerate at the topmost level—have been jaggedly cut through by glaciers and ice flows. I mention this mostly because it’s impossible to hike in this part of the world without wondering about the forces that shaped such a rocky jungle gym.

The trail traverses traditional and ancestral Mohican and Haudenosaunee land.

It was common for white settlers in the 19th century to assign fanciful names to geographic points of interest in the region to drum up tourism, according to a 1992 New York State wilderness management plan, which could explain how the moniker “Devil’s Path,” eventually came about, although the trail itself wasn’t built until the early 20th century. Because of that, it’s hard to tell how much credence they really gave the “Devil” superstitions in the region. But, as the story goes, the devil lived in the boulder-strewn "Devil's Kitchen," which is now reached from the Devil’s Path via the Overlook Trail.

The state report elaborates:

He [the Devil] and his witches traveled the remote and wild areas along the ridge of mountains westerly…strewing debris along the way; thus the poor quality of soil in the vicinity. The Devil eventually left the Devil's Kitchen area and travelled the mountains. He reportedly met his death in the then remote Stony Clove where a large upright remnant of sedimentary rock marks his supposed resting place. In 1926, this became Devil's Tombstone Campsite, the first Catskill Forest Preserve Campsite. 

Now, technically, if you’re really looking to punish yourself, you could do the Devil’s Path in a day. But in my opinion, especially if you’re coming from the city, why bother? We urbanites want more time in the woods, not less! Plus, we need a time cushion for traveling to and from the city.

Before you go

Pick up a New York-New Jersey Trail Conference Catskill Trails Map set, which includes the one you’ll need for the Devil’s Path, marked with shelters, viewpoints, water sources, and more. Make sure you have the gear you need for this particular trail and the time of year you’ll be hiking. And—especially—while we’re still in a pandemic, don’t attempt any trips you aren’t certain you can safely finish. Brush up on Leave No Trace principles and be respectful of the environment and other hikers. This is a popular trail, so if you can go during the week to reduce crowding, I recommend it.

Day one [8.5+ miles]

Leave the city as early as you can; you’ll be climbing over three High Peaks before dark, hopefully. Although we didn’t have trouble finding water, the trail can be very dry, so bring enough for the whole day.

If you only have one vehicle, you’ll want to set up a shuttle with Smiley’s taxi service—call at least a day in advance. For ~$70 - 80, depending on the number of hikers, Smiley’s shuttle will accompany you to the western trailhead at Spruceton Road. Park your vehicle and then hop in the van for a ride to the eastern trailhead.

Your destination today is Mink Hollow Shelter, but first you’ll summit the three High Peaks: Indian Head Mountain, Twin Mountain, and Sugarloaf Mountain. After the first, relatively easy two miles, there’s a lot of scrambling and frequent viewpoints. There are summit markers, I’ve read, but they can be hard to find and we missed them.

Note: If you can’t start until very late in the day, you can camp near the Devil’s Kitchen shelter, but be prepared for a very long, punishing second day over at least four High Peaks.

Day two [9.5 miles]

There’s a water source shortly after you get back on the trail, so if you have enough for breakfast, there’s no need to go out .3 miles out of your way to the water source near Mink Hollow (unless it’s really, really dry, perhaps).

It’s straight up Plateau first thing in the morning, but the reward is the mountain’s namesake, a two-mile, leisurely summit ridge through fragrant conifer forest. Plateau is the only High Peak you’ll summit today, unless you take the side trail to Hunter (where there’s a fire tower) or the unmarked trail to Southwest Hunter. Otherwise it’s straight on to the beautiful Diamond Notch Falls (bare your feet to the cold water, if you can bear it) and the shelter, a half mile away via a side trail.

Day three [7.5+ miles]

Saving the easiest miles (as a group) for last. Diamond Notch Falls is a beautiful place to have a cup of coffee and bowl of oatmeal, or to filter water for your last day, if you’re so inclined.

The last and—at 3,898 feet—highest High Peak of the Devil’s Path is West Kill Mountain, which actually has a decent (easy to spot) summit marker if you want to snap a victory selfie. Then it’s up and over St. Anne’s Peak and a steady descent to the parking lot.

If you’re so inclined and aren’t in too much of a rush to get home, head down the road in the same direction you came in on to stop by West Kill Brewing, a brewery at a historic dairy farm. There’s also a food truck, and lots of outdoor space to enjoy a beer and some tacos. (And for the designated driver, the brewery also sells beer to go, and they taste almost as good at home as after a hike.)

Another option is to swing by the famed Phoenicia Diner on your way out, which is open for take-out and outdoor dining right now.

Readers, let me know what you think! Subscribers, let me know what trips you are planning or would like to take in the near future, and how I can help find the just-right outdoorsy thing for you to do there.