Transgender hiking&climbing: 50 state high points!

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Hi! I’m Sierra Ward, pronouns she/her, and I’m trying to become the first transgender person to reach the highest point of all 50 states! As of June 2024, I’m now at 44, with just 6 more to go! (lots of pix are all the way down at bottom of this!)

In July 2023, I added a new quest: to be the first person to get to all of them wearing a dress!

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My adventures have happened in three waves: cisgender male, transgender female wearing skirts, and transgender female wearing dresses!

I started in 1997. I’d moved to Minnesota, and one early May weekend I wanted to explore the state. I looked at a paper map, and saw “Eagle Mountain, 2301 ft., Highest Pt. in Minn.” It was close to the Canadian border, in the Boundary Waters Canoe Area Wilderness. I drove up north and climbed it through leftover winter snow. The following weekend, it was on to Wisconsin’s after camping out on a sub-freezing morning. Next was Michigan’s via a waterlogged and rutted dirt road. As I began to envision doing all 50 states, and being the first person ever to do so, at Illinois’ I learned there was a national Highpointers Club, and I was not alone in my aspirations! By 2001, I’d reached 39 states!

But then I stopped: a mostly beginner-level hiker, I was honestly too scared of hiking to the high altitudes of California and Colorado, rumored undefined trails like Nevada, Idaho’s Chicken-Out Ridge, the long hike for Utah’s, rock climbing in Wyoming & Montana, and the glaciers of Oregon, Washington, & Alaska (and Hawaii’s astronomical observatory setting was said to be off-limits to rental cars). And back then, I identified as male. I remained stuck at 39.

Then in the years ahead, I began transitioning to female: growing my hair long, shaving my legs & arms & armpits & chest, wearing skirts & dresses & leggings & sports bras & other traditionally female clothing. I concurrently began developing into a true outdoorswoman, leaving safe vista points and short loop trails behind to push deeper into the wilderness. I found that nature and the wilderness don’t judge, and the outdoors always seemed safe to me, with more to fear from people than rivers, cliffs, bears, and mountain lions.

In 2010 I began to co-lead outdoors ed trips for high school students in the Santa Cruz Mountains, the Marin Headlands, Yosemite, Death Valley, and Joshua Tree, ranging from a day to a weekend to a week.

In July 2015, for the first time I wore a skirt in the outdoors: I climbed Lake Tahoe’s Mt. Tallac (9.738’). I started that hike literally scared for my life, thinking that people would attack me just for wearing a skirt, shaving my legs, having long hair. But I successfully and uneventfully reached the summit. The next day I climbed nearby Mt. Rose (el 10,785’). There was then no looking back, and it was on to hiking in skirts in Yosemite, Mt. Lassen, and many other trails and summits. Especially Yosemite.

In August 2017, wearing a skirt, I reached the summit of Colorado, 14,433’ Mount Elbert! This was my first state high point in a skirt! I considered resuming my highpoint quest, but this time with the goal of doing them all as a transgender woman, wearing a skirt for each one.

And so in May 2019, I began in earnest! I started once again with Minnesota, Wisconsin, Michigan, the same as my first visits back in 1997. Within two years, by October 2021, I’d reached 35!

By the summer of 2022 I completed the last 5 that I’d originally done as male, redoing them as female, which combined with Colorado brought me to 40.

I then also began the remaining 10 that I’d never been to as any gender. I completed

*#41, 12,662’ Mount Borah, Idaho despite its Chicken Out Ridge

*#42, 13,140’ Boundary Peak, Nevada despite endless scree and some sketchy drip-offs at the top

*#43, 13,528’ Kings Peak, Utah, which was my first overnight wilderness camping trip!

* I also added initial recon at California’s Mt Whitney, Montana’s Granite Peak, Wyoming’s Gannett Peak, and Oregon’s Mt Hood.

These more advanced summits and longer hikes, with a look forward to my remaining hikes in the future, also necessitated the purchase of additional gear. I bought my first crampons, ice axe, overnight backpack, harness, carabiners, water filter, and a lightweight tent to finally replace my 1995-ish metal-pole tent.

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In 2023, I started to redo 34 of them, this time wearing dresses! That included Colorado’s Mount Elbert, at 14,433’ the highest summit in the Lower 48 US states aside from Mt. Whitney!

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I then added more scouting on 5 of the 7 remaining ones I’d never been to.

*I pushed higher at California’s, where you need a hard-to-get permit; I had to stop at 11,500’ due to the historic snows and an incoming storm.

*In Montana I made it past Mystic Lake on the first trip as planned, but on a 2nd was held back by a bad back.

*In Oregon I pushed up to the base of Crater Rock in snow.

*In Washington I was hampered by an ice storm well short of Camp Muir, and turned around

*I’d purchased a plane ticket to Hawai’i, but respectfully canceled due to the fires when the state government advised tourists not to travel to any island, to free up seats for locals and emergency workers.

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2024 has arrived. It’s time to push farther!

And I started off well, finally summiting California’s Mt. Whitney, #44, 14,505’! And wearing a dress! Whitney is the highest summit in the US outside of Alaska, about a 21-mike roundtrip hike with 6.200’ of vertical, both up and then again down. Phew! It was my 4th permitted attempt, the 3rd of this year: having turned back on #1 in June 2023 as noted earlier, then #2 in May 2024 due to dangerously high snowmelt runoff at a stream, and #3 in mid-June 2024 due to high snow at the cables. But I persevered and was patient, and finally did it!

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For the remainder of this summer of 2024, I have various trips planned to 5 of the remaining 6: Montana, Wyoming, Oregon, Washington, & Hawai’i, though summits will likely extend into 2025.

I’ll also be returning to about a half-dozen others wearing dresses for the first time.

And I’m saving Alaska, #50, for summer 2025 or 2026.

So here’s what I have remaining:

Oregon: Mt. Hood, el. 11,249’

Montana: Granite Peak, el. 12,807’

Hawai’i: Mauna Kea, el. 13,796’

Wyoming: Gannett Peak, el. 13,804’

Washington: Mt. Rainier, el. 14,411’

Alaska: Denali, el. 20,310

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And here’s where GoFundMe comes in. All of this travel and climbing are becoming increasingly expensive: not only airfares (I don’t plan on swimming to Hawai’i or driving to Alaska), rental cars, gas which has been at record prices, lodging, food, and incidentals, but also some climbing equipment and clothing which I don’t currently have or recently purchased: mountaineering boots, a heavy expedition jacket, climbing rope, avalanche beacon, mountaineering training/classes/practice, as well as guides. I’ll have a celebratory dinner with friends and trail companions after a few of them: I’ll have companions on many hikes, partially as protection due to the ever-present real threat of violence against me.

Not to worry, I’m not going to run up inappropriate bills: my primary daily food staple is sports bars (the kind you eat, not the kind you eat & drink at), and I’m not one to live a lavish lifestyle, regularly sleeping in my car.

Not to mention that I'm in my 7th year as a college counselor at a public high school, so I don’t make much money, particularly for the San Francisco Bay Area. Any leftover unused funds, I’ll donate to Campus Pride, given my line of work; and The Trevor Project, because I want to save lives & improve mental health: about 50% of trans teens attempt suicide, and many of us are homeless, unemployed, fired, kicked out of our homes, bullied, assaulted and even murdered just because of our appearance. I don’t want to be wealthy, I just want my dignity and to inspire others.

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And here's part of why I do this, some of my motivation and symbolic mountain climbing in the face of great obstacles: my own lived experience of how bad it is for us transgender people (all of the following verifiable, in writing via emails).

* A recent former private high school employer of mine, Menlo School in Atherton, CA (the private school), had programming for students and staff strongly encouraging diversity and inclusion; an LGBTQ affinity group; a mission statement encouraging risk-taking, being your authentic self, and making the world a better place; a large rainbow flag in the quad; board directives to do better in diversity; and had been criticized by its accrediting agency more than once regarding aspects of its diversity.

* Yet still, my three superiors (their current Head of School, current Upper School Director, and former Director of College Counseling) called me into a meeting after I only wore a skirt for work, and was reported/turned in to them by someone else who didn't even work for the school.

* They then further told me in writing that it was possible that “counselors, admissions staff, parents, students” may react negatively to my “choices” and that they were concerned that “such a negative reaction could compromise your ability to establish close, trusting relationships with your constituent groups and thus compromise your ability to be effective in your work here”

* They told me to “develop a plan to mitigate the potential negative impact of your appearance in skirts” that went beyond my own personal coming-out process

* They referred me to their employee assistance program; made me agree to a vague “no more surprises” even if that was on my own personal time.

* They had me agree to “no more surprises”

* They then isolated me in writing from the 5 colleagues who I’d requested in writing to protect me and be my advocates, despite an advocacy program being a core program of the school. Yes: they’d earlier asked me to make a plan, so I made a plan, but they denied it, in increasingly controlling behavior and abuse of power.

* They tried to reduce my coming-out, public blog to one paragraph, more controlling behavior.

* They ignored my 3 separate requests to use female pronouns for me. Yes, another part of my plan, again denied by them, yet more controlling and abusing their power.

* And they continued to focus in writing on negatives and concerns - especially what potential negative reactions from students - rather than ever saying even one thing positive, affirming, validating, or empowering, or acknowledging my stated purposes of upholding the school's mission and values, saving lives (preventing suicide) and mental health, and just being me. Never once were they enthusiastic, when I was seemingly living the school’s mission.

It’s been 9 years since all of what I’ve written above started, and I’m still awaiting justice for their wrongdoing. All the while, climbing physical mountains, first in skirts, now in dresses, while also having started my hormone therapy (testosterone-blocking pills and estrogen patches) in 2019, with my gender-affirming surgery finally approaching and its initial medical procedures now underway!

This is about social justice, civil rights, freedom, and accountability of those who so clearly did wrong to me.

Skirts are clothing, skirts are legal: one of the most commonly-worn garments around the world. I no longer own pants (unless you consider leggings by themselves to be pants), and have now worn only a skirt (or sometimes a dress) to work every day for nearly 8 years, as well as everywhere else (like when running, and my volunteering with musical theater and ballet).

It wasn't pronouns, using a bathroom, having surgery, altering a driver's license, changing a birth certificate, wanting to play sports. It was a skirt.

Our stories need to be told rather than silenced and covered up, so that we can stop harm from happening to others, which prevents us from thriving: many of us are barely surviving, and some of us are ending our lives because of the environments we have to endure. It’s taken me a long time to begin to emerge from what Menlo did to me, and I’ll never be able to purge all of the memories or get back the years that they delayed my coming out and transition.

But I consider myself fortunate to have found 100% acceptance at every other school I’ve worked at: Bucknell University, Alto International School/Silicon Valley International School, Menlo-Atherton High School (the public one), Terra Linda High School, South San Francisco High School, and Saratoga High School. This includes administrations, staff, students, parents, alums, as well as my professional associations! Thank you all! With all of you, I’ve worn skirts and dresses every day, used female pronouns, began my hormones, began my medical procedures, and changed my name!

I’ve also worn a skirt or dress now for all 44 state high points so far, and will be on every remaining one (I have a plan for the highest summits so it’s not a dangerous billowy skirt that could catch on rocks, ice, or snow!), so I can show people what women & girls can do, and what those of us who wear skirts can do. I repeat: it was a skirt.

Transgender people have especially long and steep trails to climb, with lots of obstacles in our way, some thrown in our way by people. But I’m trying to give some hope to one of the most vulnerable, marginalized, powerless populations, and make lives better for everyone who follows in my shoes or boots. I’m trying to blaze trails for others to follow, create easier paths for others not just on mountain & other wilderness and outdoors journeys, but in life, including in the college counseling and admissions field I've been part of as I enter my 25th year. I’m trying to gain acceptance for us as human beings. I’m trying to make the world a better place.

And if you don’t think what I’m doing is a big deal: those of you who were assigned male at birth like I was, I'd ask you to grow your hair long, and shave your legs, and wear leggings, and wear a bra, and wear a skirt or dress, and you’ll see how your life changes, how people react to you, how your life becomes more difficult, especially at employers who control your paycheck and therefore your life. We need to be treated equally at our places of employment, and being able to wear a skirt like any other employee without employer intervention or interference should qualify as a most basic form of being treated equally.

On an even larger scale, I’m also doing this for anyone who’s ever encountered obstacles just because of who they are and how they are different and how they express themselves as a legally protected class of people: if you want to wear a cross, a yarmulke, a hijab, a turban, a sari, a wedding ring, a photo of your same-sex partner on your desk at work, if you are Asian, Black, Hispanic/Latinx, Native American, if you use a wheelchair or cane, if you are pregnant, if you have cancer or other physical or genetic disability (my Mom was a breast cancer survivor, and lost some of her hair). Let’s climb together.

Thank you so much for your consideration, and any financial assistance you can provide on my quest for 50! And please follow my journey on Instagram at @SierraTheMusical!

Below are a bunch of photos and some of the history!

California: Mount Whitney, 14,505’

June 19, 2024 in a dress! This was #44 for me, 21-miles roundtrip, 6,200’ vertical and then all the way back down too, highest point in the US outside of Alaska! It was my 4th Whitney permit, the prior 3 having been stopped by weather and nature. It included the infamous/notorious snowy cables section, which I did without microspikes or crampons after watching a few others. It was also the first one since I’d changed my name to Sierra: start big!

I dedicated my climb to Esmé Page, a 14-year-old 9th grader from Claremont CA who had ended her life in 2015 after being bullied while exploring gender; Esmé had been a family friend, and a few weeks after her suicide I’d finally had the courage to begin wearing skirts for work, to raise awareness, be a role model, give hope, and try to make the world a better place. 2 weeks later, Menlo called me into that meeting, put my coming-out and transition on hold, and never even acknowledged Esmé or any of the other kids committing suicide, never recognized the positive work I was trying to do, only concerned about potential negatives of my coming out at Menlo.

This is the mountain I continue to climb.

Colorado: Mt. Elbert, 14,433’
August 5, 2023 in a dress. I’d thrown out my back a week and a half earlier, but still did this!

August 19, 2017, in a skirt
This was high point #40 for me, the first for me now identifying as a transgender woman, the first one I wore a skirt for, and first one since 2001 back when I identified as male!

Utah: Kings Peak, 13,528’
Sept. 4, 2022 in a skirt. This was #43 for me. 28.8 miles roundtrip, 5,160’ vertical, also my first solo overnight camping trip!

New Mexico: Wheeler Peak, 13,167’
July 17, 2023 in a dress

July 24, 2022 in a skirt, so much wind!

Nevada: Boundary Peak, 13,143’
July 30, 2022 in a skirt. This was #42 for me! A little technical at the top, watch your step!

Idaho, Mount Borah, 12,662’

July 18, 2022 in a skirt, this was #41 for me! I’d never done anything even close to this technical before: Chicken Out Ridge is no joke. About the hardest trail you’ll do, SO steep in such a short distance!

Arizona: Humphreys Peak, 12,637’

July 18, 2023 in a dress. This was also the first one where I saw another person wearing a dress! Yippee!

Sept. 5, 2021 in a skirt

Texas: Guadalupe Peak, 8,749’

October 31, 2021 in a skirt. Sadly, many folks on the trail thought I was wearing a skirt as part of some Halloween costume, not knowing I was transgender. This was my first one where I started well before sunrise, with a headlamp, because of forecast heat. I dedicated it to Texas native Larry McMurtry, author of Roads, one of the travel writing books that developed my enthusiasm for travel!

South Dakota: Black Elk Peak, 7,242’

July 14, 2023 in a dress, warm morning so I was quite sweaty, I think I’d overdressed! Highest point between the Rocky Mountains and Europe!

July 24, 2019 in a skirt. I dedicated this one to the eponymous Black Elk, of the Oglala Lakota, whose book we had read at Menlo School when I taught as part of our World Religions teaching team, then the required yearlong 9th grade history class. The book had been very impactful on me.

North Carolina: Mt. Mitchell, 6,684’

July 9, 2023 in a dress. #1 highest point on the East Coast! So pretty!! Also 8am was ideal because there was no one else in the parking lot & I had the summit to myself, so it was super quiet, just me and the birds.

July 24, 2020 in a skirt (and mask, per pandemic recommendation with other folks around!). Scattered rain showers & intermittent low clouds & fog all the way down to the ground. SO lush, green, and beautiful woodsy, forest scents!

Tennessee: Clingmans Dome, 6,643’

July 8, 2023 in a dress

July 23, 2020 in a skirt (and mask, per pandemic recommendation with other folks around!). I’d dedicated this one to Nashville and all of its amazing country music that I love, bringing my 40+-year-old guitar!

New Hampshire, Mt. Washington, 6,288’, highest point in New England!

June 27, 2022 in a skirt; SO WINDY AMD STORMY!

Virginia: Mt. Rogers, 5,729’

July 8, 2023 in a dress

July 25, 2020, in a skirt; I did this one for the One Love Foundation, founded after UVA student and lacrosse player (hence my lacrosse t-shirt) Yeardley Love was murdered by her former boyfriend, raising awareness about dating and relationship violence

Nebraska: Panorama Point, 5,429’

July 14, 2023 in a dress, as a massive hailstorm approached!

July 24, 2019 in a skirt

New York, Mt. Marcy, 5,343’

June 29, 2022 in a skirt, yes it was as windy as it looked, but crisp and gorgeous!

Maine, Mt. Katahdin, 5,268’

June 26, 2022 in a skirt, holding my copy of She’s Not There, by Jennifer Boylan. Boylan had been a professor at Maine’s Colby College when she went through her transition and gender-affirming surgery in the late 1990’s-early 2000’s, and a colleague gave me her book around 2004, which I read in one afternoon and it was life changing, for the first time in my life knowing there was someone like me. I was working at Bucknell, and began to speed up my transition and come out to colleagues, which went fine even at a college in rural Pennsylvania. I still don’t know how things went so wrong at Menlo School,, in the Bay Area of California, a few years later when it should have been so easy.

Oklahoma: Black Mesa, 4,973’

July 16, 2023 in a dress

July 28, 2019 in a skirt, with my cowboy boot from the National Cowboy Museum in Oklahoma City!

West Virginia, Spruce Knob, 4,863’

July 2, 2023 in a dress, wanting to dance and twirl across this mountaintop! Maybe I did, just a little. :-)

July 26, 2020 in a skirt

Georgia: Brasstown Bald, 4,784’

July 9, 2023 in a dress

July 23, 2020 in a skirt (and mask, per pandemic recommendation with other folks around!)

Vermont, Mt. Mansfield, 4,393’

June 28, 2022 in a skirt, wearing my link cow spots hat, very apropos in Vermont!

Kentucky, Black Mountain, 4,145’

July 8, 2023 in a dress, they really need to build a viewing tower or clear a path through the trees to a nice vista!

July 24, 2020 in a skirt, quick photo and gone, trying to avoid an oncoming thunderstorm at the highest point in the area, never a good thing!

Kansas: Mt. Sunflower, 4,039’

July 15, 2023 in a dress; I’d bought this at a Target since it seemed Prairie-Girly to me :-)

July 28, 2019 in a skirt, leaning strongly into a strong High Plains wind!

South Carolina: Sassafras Mountain, 3,560’

July 9, 2023 in a dress

July 23, 2020 in a skirt, holding a mini Hilton Head lighthouse, where my parents had taken us on vacation a few times when we were kids

North Dakota: White Butte, 3,506’

June 28, 2023 in a dress, flashing #1 since this was my first wearing a dress! It began my 3rd cycle, High Points Dresses. And I was smart to wear a billowy long-sleeved shirt, since 4 years earlier here I’d been eaten alive by mosquitos on the sheltered, no-wind lower approach trail.

July 23, 2019 in a skirt, super windy at sunset up high on the plains!

Massachusetts, Mt. Greylock, 3,491’

July 3, 2023 in a dress, flashing #10 since this was the 10th one of my 3rd cycle (High Points Dresses)

July 27, 2021 in a skirt, holding a photo of my brother and his wife, both graduates of Williams College at the base of the mountain

Maryland: Hoye Crest, 3,360’

July 2, 2023 in a dress

July 26, 2020 in a skirt, as I added a stone to the ever-growing pile at the summit (which had been knocked down by someone prior to my next visit 3 years later)

Pennsylvania, Mt. Davis, 3,213’

July 2, 2023 in a dress, pointing at my Bucknell University hat, where I did my undergrad work (proud English major!), where I got my start in the admissions & college counseling field, and where I started my coming-out and transition, with no problems and complete support from colleagues including my supervisor)

July 26, 2020 in a skirt, wearing my favorite orange and blue Bucknell t-shirt (which was unfortunately stolen 2 years later). GO BISON!!

Arkansas: Mt. Magazine, 2,753’

July 12, 2023 in a dress

July 27, 2019 in a skirt; I was pretending to make signals with my two flags, for the random person taking my photo!

Alabama, Cheaha Mountain, 2,407’

July 10, 2023 in a dress

February 21, 2020 in a skirt, holding a copy of Alabama native Harper Lee’s To Kill A Mockingbird, which is also set in Alabama

Connecticut, Mt. Frissell, 2,380’

July 4, 2023 in a dress; I was wearing a Danskin dance dress, so I’m doing a ballet 5th position, in hiking boots, on an uneven rock that had also been rained on!)

July 26, 2021 in a skirt

Minnesota: Eagle Mountain, 2,301’

June 30, 2023 in a dress (hidden under my thick bulky ski pants and thick jacket despite the 75 degrees and humidity, SO MANY MOSQUITOS! Glad I’d bought a mosquito net for my head!)

June 15, 2019 in a skirt (so few mosquitos!) This was my first summit of my “2nd cycle,” now identifying as a transgender woman, wearing a skirt (High Point Skirts), re-doing all the ones I’d done as male.

Michigan: Mt. Arvon, 1,979’

June 20, 2023 in a dress, my 4th one of my 3rd cycle (High Point Dresses)

June 15, 2019 in a skirt

Wisconsin: Timms Hill, 1,952’

June 30, 2023 in a dress, my 3rd one of my 3rd cycle (High Point Dresses)

June 16, 2019 in a skirt, and “You’ll Find Me In the Mountains” t-shirt!

New Jersey: High Point, 1,803’
July 5, 2023 in a dress

July 27, 2020 in skirt, holding my vintage, New Jersey native “The Boss” Bruce Springsteen concert t-shirt, from his Born in the USA tour, October 1984!

Missouri, Taum Sauk Mtn., 1,772’
July 12, 2023 in a dress

July 26, 2019 in a skirt

Iowa: Hawkeye Point, 1,670’
July 13, 2023 in a dress. Note that since my prior visit in 2019, someone had unfortunately stolen the far left pole with state signs, either that or a tornado took it? :-(

June 17, 2019 in a skirt

Ohio, Campbell Hill, 1,550’
July 1, 2023 in a dress (standing in a nice dress, staring at the sunset, babe…)

December 27, 2019 in a skirt

Indiana, Hoosier Hill, 1,257’
July 1, 2023 in a dress, standing on the highest ~natural point at the high point!

December 27, 2019 in a skirt

Illinois, Charles Mound, 1,235’
August 1, 2020 in a skirt

Rhode Island, Jerimoth Hill, 812’
July 4, 2023 in a dress

July 26, 2021 in a skirt

Mississippi, Woodall Mountain, 806’
July 11, 2023 in a dress

February 20, 2020 in a skirt (yes it was snowing in Mississippi!!)

Louisiana, Driskill Mountain, 535’
July 11, 2023 in a dress (and completely unnecessary but oh-so-fashionable-with-a-dress hiking boots!)

February 18, 2020 in a skirt

Delaware, Ebright Azimuth, 448’
July 6, 2023 in a dress

July 26, 2020 in a skirt (in the height of the pandemic I wasn’t about to ask anyone to take a photo for me, but I didn’t bring a tripod, and there was nowhere to put a camera except the ground!)