Trip Report
Stowe Mountain Trip Report from October 17 – 19, 2025
For years, my girlfriend has been telling me one thing over and over—there is no way I’ll be able to surprise her with a proposal. For most of our relationship, I totally believed her in this notion. With us recently celebrating our five-year anniversary, it made sense that she would see it coming. Yet despite this, I was determined to prove her wrong by tricking and surprising her in a way she wouldn’t think was possible, and the best spot to do that would be at a ski resort. Right? While I’ve been an avid skier and have been my whole life, my girlfriend has fallen into the sport through our relationship. She enjoys the sport, but by no means is as passionate about it as I (understandably).
After countless conversations with her where she fantasized about proposal ideas, I knew I had a difficult task ahead of me. She wanted it to be special, so it couldn’t be in our home state of New Jersey, neighboring New York City, my hometown of Toronto, or in sub-zero temperatures while actually skiing. Turns out those four places are where we spend a lot of our time, so that slimmed my ideas down significantly. Oh, and she wanted a photographer for the moment, meaning this couldn’t be some spontaneous, impromptu idea either.
Thankfully, we were planning a weekend up to Stowe Mountain this fall for its annual Harvest Festival, and I noticed that this Vermont gem checked all the boxes. We were going up there in the fall, her favorite time of year (without sub-zero temperatures). We were visiting a new place we’d never been to together. We were staying at a ski resort (which means a lot to me). We had an incredible weekend planned with great meals, activities, and exploring. And it had the odd connection of being only 45 minutes from the small town my girlfriend grew up in as a baby.
If you ask my girlfriend, our relationship, looking back, seemed like fate. We met on the other side of the country while attending the same college in southern California, and it was only after a couple of months of knowing each other that we made the connection that she was born in the small town of Newport, Vermont—a town on the very same lake my family has had a cottage on for 111 years. From then on, we became best friends, then Covid, and then we started dating once the pandemic allowed both of us to return to school.
Proposing in Stowe felt like it helped to tie our story full circle, with the added benefit of it having a reputation for being a crown jewel in terms of New England’s fall beauty.
So I knew Stowe would be a great place to propose, but now I actually had to execute on this idea, as a complete surprise. The top of Stowe’s gondola seemed like an obvious pick. Sweeping views, fall foliage below us, an activity I could plan in advance without suspicion, and a precise location to give the photographer (who would be hiding) a place to stake out. I was a little shaky on everything going smoothly, but I felt like this was my best shot. I shared my grand plan with Samara, the Communications Manager from Stowe, at Ski Vermont’s annual New York City Media Night, and she had the idea to take my plan one step further.
What if, with the help of Stowe, they orchestrated a fake tour of the mountain to completely throw my girlfriend off track, so she would suspect nothing? What if they could also provide the photographer with a Stowe jacket to raise zero suspicion about her presence? What if this tour allowed us to sneak up the gondola a little early before opening to the public, so this special moment could be completely private to just us?
I instantly took her up on her offer, and then I not only felt good about my idea but truly confident that I could fully surprise her.
The night before the proposal, I had a hard time sleeping. Regardless of all of the intricate planning that had been done in the weeks prior, one of my biggest struggles still lay ahead—dressing appropriately. For anyone who knows me, I’m a pretty casual dresser. So dressing up nice, without a prompt from my girlfriend, along with getting her to dress nice for a seemingly casual gondola ride, without raising any suspicion, would be a challenge. Thankfully, I had been playing up the fact for a week that I wanted to treat this weekend nicely, and “match the vibes that Stowe gives off,” dressing my best for the entire weekend. It worked.
We met Lisa Bryan, the Assistant Manager of Guest Services, at the base of the gondola at 9:10 am, for our “Work Tour” that brought us up the mountain right before it was opened to the public.
We were shown around at the top, and then left with some time to “explore the area by ourselves.”
As we walked around, I “naturally” led us to the rock I planned to get down on one knee beside, and I popped the question.
“Will you marry me?”
She said yes!
At first, there was confusion. “Is this really happening?”
Then, there was simply laughter. “Oh my God!”
Then, there was crying. “Oh, this is actually happening.”
It was everything we both had dreamed of.
From there, we had an incredible weekend at Stowe ahead of us, filled with great food, activities, and events that only built on our special moment.
- Related: How to Plan the Perfect Ski Wedding
Toll Road
I’d argue Stowe’s historic Toll Road is the most underrated attraction in the region. While fall foliage traffic plagued the town of Stowe’s center, along with Waterbury and nearby areas, the Toll Road felt like a complete escape that brought you into a world you had all to yourself. The 102-year-old 4.5-mile road follows the Toll Road ski trail and gives you a great perspective of the entire resort and Smugglers Notch. I loved how we could take as much time as we wanted driving up and down the mountain, with plenty of pull-outs along the way to stop, walk around, and soak in the views.
While the Toll Road may not feel as unique as a gondola ride for non-skiers, if a gondola ride feels pretty normal and you are only looking for one way to get to the top of the resort, I’d opt for the Toll Road from both a crowd and affordability perspective.
Harvest Festival
This unique event was the catalyst for us deciding to go up to Stowe in the first place. The event breathed life into the ski resort before any snow had started to fall. Featuring live music, local food vendors, and family activities, the Harvest Festival was a great way to soak in the views of Stowe from the base, where the fall foliage looked its best. As a local band played folk music, I sat in an Adirondack chair, wondering if there was anything more Vermont than what I was experiencing in that moment in time. It was a wonderful thing to do after riding the gondola.
Gondola Skyride
Arguably, Stowe’s most popular attraction in the fall, riding Stowe’s iconic red gondolas, is a breathtaking experience. With Mt. Mansfield being the tallest mountain in Vermont, the top of Stowe offers breathtaking views of the White Mountains in New Hampshire (including Mt. Washington), and sweeping vistas that stretch all the way to Canada. If you are looking for more of an adventure, you can hike from the top of the gondola to either the Lower Lip or the Chin of Mt. Mansfield to get the best 360º views.
Hiking
Stowe Mountain Resort, along with the surrounding area, offers a robust system of hiking trails for any ability level. Whether it’s a casual stroll along Stowe Mountain’s Spruce Peak Community Pathways or taking on a section of Vermont’s Long Trail, you have no shortage of hiking options. After driving the Toll Road and taking a scenic gondola ride, my fiancée and I (first time using that word) opted to make my way up Spruce Peak via the Barnes Camp Loop to get a different perspective on the ski resort and the surrounding area, which had the added advantage of us being the only ones hiking that side of the resort.
Smugglers Notch
From the top of the Sensation Quad on Spruce Peak, Smugglers Notch ski resort is only 2,600′ away. In the summer, the drive through Smugglers Notch, which the ski resort is named after, on Route 108, takes a mere 15 minutes, and offers a winding mountain road that is typically only found out West. It’s a great, quick drive to do right beside Stowe that brings you into a boulder field environment that seemingly appears completely out of nowhere.
Nearby Attractions
Countless additional nearby attractions build on why Stowe is a great place to visit, even outside of the ski season. The Ben & Jerry’s in Waterbury is a great attraction for families and ice cream lovers alike, and serves as a core memory to me from when I visited as a child. The Cold Hollow Cider Mill allows you to get a classic apple cider donut and an apple cider slushie (seriously underrated if you haven’t tried it).
Great dining options at the mountain and in town leave you struggling to narrow down your meals. We opted for American Flatbread, which has the best flatbread we’ve ever had, Butler’s Pantry, and the Stowe Bee Bakery.
Vermont Route 100, which winds its way through the town of Stowe and then past other hallmark ski resorts, including Sugarbush, Killington, and Okemo, is often coined as one of America’s most scenic drives for a reason and is a great route to return on if you are visiting from the south.
After experiencing Stowe for the first time, it lived up to all its very high expectations. After wondering why this town and ski resort is a place not only well known amongst the ski community, but also generally in the American zeitgeist, I finally get it. And now, Stowe will mean even more to me with such a special weekend.
A special thanks to Samara, Cecille, Lisa, Coryn, and the entire Stowe Team that helped me pull off my proposal surprise. I couldn’t have done it without you!
