Hiking to Great Heights for Proposal Photography above Windham New York

By Jonathan Ment Photography

The lure of the mountains here in our part of the Catskills has always been strong for a Catskills photographer. Their beauty is one of the things that drew me here to make my home.    And as a photographer, they never disappoint.

For so many day trippers and weekenders, they’re a reason to head to the country.

Some folks are obsessed with climbing to the top of as many as possible – so called peakbaggers, or “summit-focused hikers, climbers and mountain lovers.”

For me, the occasional hike whether alone or with a small group of friends or photography clients, is just another way to enjoy this beautiful part of Upstate, NY. 

Lately, as busy as life can get, I’m more likely to explore a new trail or one  I haven’t visited recently in connection with a photography session, than for my own pleasure. The beauty of being a photographer who happens to live in this area, is how beautiful my #officefortheday turns out to be. As pretty as the views are from below, the scenery from atop some of these mounds of earth and rock called mountains is always impressive.

In addition to trekking parts of the Devil’s Path, and climbing to the top of Hunter Mountain, to photograph surprise proposals or engagement sessions, in recent years I have also explored much of Lake Minnewaska State Park, the trails above and below Kaaterskill Falls, all of the Windham Path and more. But one trail I hadn’t climbed to meet a couple with my cameras was Windham High Peak – until recently.

Quinn reached out via catskillsphotographer.com less than a month before the planned dateduring which he intended to propose to his (now) future missus, Laura.   The plan wasto ask her to marry him atop Windham High Peak, one of more than 30 peaks in the Catskills that reach or exceed 3,500 feet in elevation.  As is often the case, I was able to accommodate the couple on their scheduled visit.

The moment  should be captured in photographs.

“Is that something you do?,” he asked.

I have a sort of simple rule when it comes to photography, unless there’s a good reason not to, I try.  The rule is that I always say:

 “Yes!”

From that point, it’s just a question of terms and logistics. 

A photography session at a vacation rental or AirBnB is a little simpler than one in the middle of an eight mile round trip hike. Naturally, the session that includes a  hike requires a bit more of my time and though the fee doesn’t equal that of a like number of hours for a wedding or reunion, there is some consideration of time and effort.

While I always ask for a photo of the couple I will be looking for, if available, when a session involves some scenic overlook, we also share when possible a photo of the location. Fortunately these days there aren’t too many points you can walk to that haven’t been documented by someone and shared on the web.

It’s important that I’m the one waiting, casually of course, for the couple to arrive, so trail details (thank you again Google) are also helpful.

Mishaps are possible on any hike, so a little bit of luck doesn’t hurt either, as well as leaving extra time for the unexpected.

When the day comes, with cameras packed and ready, a little trail mix and plenty of water in the bag, I set out well ahead of when they plan to start to cement the likelihood I won’t be passed on the trail along the route.

I was enjoying the view (and the trail mix) at the designated spot near the summit, and considering angles for framing photography, when I heard a couple in the near distance. I don’t recall what was being said, but it would turn out to be Laura’s distinct voice that reached me first.

Surrendering the rock to them when they reached it, (accurately) posing as a lone hiker, I moved back from the overlook and said I just wanted to take a few more pictures as the light was perfect.  

Then, as quickly as it always seems to happen, the moment arrived and Quinn was on bended knee.

She said “yes” too, of course and after quick introductions we took some less candid photographs around the overlook.  It was about five years earlier that Quinn knew for the first time he would eventually propose to her at that spot, and thatQuinn and Laura would spend the rest of their lives together.

They toasted their engagement with supplies he had carried up and we agreed I would leave them there to soak in the moment, each of us leaving as we had come – me as a solo hiker.

A hike down from a high peak is both easier and quicker than a hike up. Thank you gravity! For me, this descent was also a chance to think more about my surroundings and less about the job ahead (which was now behind.) I had taken a few cellphone photos on the way up and revisited them for their timestamps on the way down to gauge my progress and estimate when I might make it home to my own missus.

While I am by no means a travel blogger and this is not a hiking blog, I feel compelled to share a few thoughts about the diverse and beautiful route to and from Windham High Peak from the trail head on state Route 23 across from the NYSDEC parking lot off Cross Road. This is of course far better documented by those who do it for trail-centric websites.

The lowest section of the trail, also the flattest, must parallel the highway for a bit as road noise in the distance is not uncommon. But without realizing quite when, that road noise melts away as one becomes immersed in the forest.

While this, like most DEC trails, is well marked it is not impossible as I found out twice on the way up to lose the trail for a moment. For me, it was the simple act of stepping back to take photos that prompted me to ask ‘where did those blue trail markers go.’ Fortunately, while there isn’t always a marker within sight ahead of you, if you turn around you’ll likely see from whence you came – helping reestablish the route along what’s known as the Escarpment Trail.

The walk is filled with different environments from hardwood forests to bogs with split log foot bridges. If you’ve researched the route and know the view of the Blackhead Range,you’ll realize you’re near the top when it starts to peak through the trees. Alternately, while several patches of shorter trees might deceive you in to thinking prematurely you’re near the summit, a battered 3500 foot sign beside the winding hobbit trail (Laura suggested that connection) confirms the moment you ultimately are.

On your decent, near the bottom, there are a few more detailed navigational aids (trail signs) in the vicinity of a lean-to and shortly before you reach them that road noise that drifted quietly away on the climb subtly returns.

A hike I thought might take 2 hours in each direction, excluding time spent behind the lens, was closer to 2:15 up and 85 minutes down.

There’s an organization for folks committed to climbing all of the 3,500 + summits and though I doubt I’ll ever be a member, it’s always been an idea in the back of my mind. 

When will I climb the next one? That all depends. It could depend on when and where you’re planning to propose.

Let’s talk about your photography plans … and your proposal plans!

Thanks for reading,

Jonathan Ment, Photographer