Lindsay Raymondjack Photography

Lindsay Raymondjack Photography

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A Winter Proposal at The Hermitage Inn in Vermont

There’s something about a Vermont winter that makes big moments feel even bigger. Quieter, warmer, more intentional. Julie and Chris’ proposal at The Hermitage Inn was exactly that kind of moment: snow dusted, candlelit, and full of the kind of anticipation you can feel in your chest before anything even happens.

Friends practice marriage proposals in from of the wine rack
Opus One wine at the Hermitage Inn Wine Cellar Proposal
the perfect proposal moment of yes in the Hermitage Inn Wine Cellar in west Dover Vermont
Just said yes proposal portrait in the library at the Hermitage Inn
black and white detail portrait of bride to be and new engagement ring
the Hermitage Inn front door

How the Proposal Plan Began

The original plan started, as many good Vermont stories do, on a ski slope. Chris first reached out through Julie’s best friend Kathleen, who was quietly doing research for a Vermont proposal photographer. The idea was simple at first, something slope side at Mount Snow, maybe even on snowboards. But as the details unfolded, Chris realized he wanted something more intentional, something more them. Especially after learning that Julie had once made it very clear: if he ever proposed while she was wearing snow pants, the answer would be a firm “Nope, try again.”

From there, the plan evolved through a few versions before landing on something far more intimate and elevated. A private dinner celebration at The Hermitage Inn, with the proposal tucked into the inn’s wine cellar just before they sat down to eat. Julie thought she was heading into a quiet ski weekend. No surprises, no audience, no elaborate plans. But behind the scenes, friends were on the move.

Choosing The Hermitage Inn for a Vermont Engagement

Friends had arrived early, some traveling from out of state, gathering at the bar upstairs while we prepared downstairs. One of the biggest logistical challenges was keeping it all a secret. Chris had to carefully manage location sharing so Julie wouldn’t notice her people slipping quietly into Vermont.

Down in the wine cellar, the energy shifted into something almost cinematic. The space was warm and softly lit, filled with that unmistakable feeling of something about to happen. I arrived early to adjust the lighting and prep the room, while Julie’s friends helped stage the surprise, practicing their timing and even helping me by posing in mock proposal setups on one knee. Those behind the scenes frames ended up being some of my most favorite images of the entire evening.

Why The Hermitage Inn Is Perfect for a Vermont Proposal

The plan was precise. Friends would hide behind the wine racks. Chris would guide Julie downstairs. The moment would unfold all at once. And it did. Julie stepped into the cellar expecting nothing, and walked directly into a room full of love. Friends emerged from behind the racks. Chris dropped to one knee. The room filled with laughter, shock, and that rare kind of joy that only happens when surprise and love collide perfectly.

Outside, it was a true Vermont winter, chilly and blustery with a light dusting of snow. But inside, the inn was glowing with twinkle lights, evergreen touches, and that unmistakable holiday warmth that makes you want to stay a little longer than planned. The staff was gracious and accommodating, helping every piece of the surprise come together without a single seam showing.

If there’s one takeaway from Julie and Chris’ day, it’s this: bring your people. Plan the weekend. Let the moment stretch into a celebration. Because in places like The Hermitage Inn, love doesn’t just happen in an instant. It settles in, gathers warmth, and becomes something you carry with you forever

Bring your people. Plan the weekend.

If there’s one takeaway from Julie and Chris’ day, it’s this: bring your people. Plan the weekend. Let the moment stretch into a celebration. Because in places like The Hermitage Inn, love doesn’t just happen in an instant. It settles in, gathers warmth, and becomes something you carry with you forever

I’d love to help! Just so you know, most who reach out have no plans at all. Turning vague ideas into a thrilling plan is my specialty.

** Written with cold hands and a warm heart, somewhere on a Vermont mountainside.

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Reach out and tell me about your wedding. I photograph across Vermont and New England and I love a couple who shows up with a celebration that surprises everyone.

Most couples who reach out have no plan yet.