Winter in Woodstock

Winter in Woodstock
📍 Woodstock, Vermont

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If there’s one place that embodies the magic of winter in New England, it’s Woodstock, Vermont. With snow-dusted trees, charming colonial buildings, and the cozy warmth of the Woodstock Inn, this town feels like stepping into a storybook. Recently, I had the chance to spend a day here, and it was nothing short of enchanting. Dressed in a chic yet practical outfit for dinner — my faux fur jacket layered over a classic Black Watch tartan dress from Tuckernuck, paired with Sarah Flint heels — I felt perfectly suited for the picturesque backdrop.

A Stay at the Woodstock Inn

The Woodstock Inn is the centerpiece of this idyllic town, and for good reason. From the moment you step inside, you’re greeted with roaring fireplaces, inviting seating areas, and the warmest hospitality. The rooms are a perfect blend of modern luxury and traditional New England charm, with cozy bedding and thoughtful touches that make you feel right at home. During your stay, you can take full advantage of the on-site amenities, from the indulgent spa treatments to the outdoor fire pits. It’s not just a place to stay — it’s an experience that immerses you in the magic of Vermont winters.

Dining at the Red Rooster

No visit to the Woodstock Inn is complete without a meal at the Red Rooster, the inn’s signature restaurant. The menu is a love letter to Vermont, featuring locally-sourced ingredients crafted into refined, seasonal dishes. I opted for the New England clam chowder squash soup followed by the chicken salad sandwich, both of which were absolutely delicious. The atmosphere strikes the perfect balance between upscale dining and laid-back comfort, making it an ideal spot to linger over a meal. And don’t skip dessert — the maple bread pudding was the perfect sweet ending to a cozy evening.

Exploring Woodstock in Winter

Beyond the inn, Woodstock offers plenty to explore, even in the chill of winter. A stroll down Main Street reveals an array of boutique shops and cafes, all adorned with twinkling lights and festive wreaths. We spent quite a bit of time at F.H. Gillingham & Sons, a general store that’s been a Woodstock staple since 1886, picking up locally-made maple syrup and woolen mittens. For a bit of outdoor adventure, nearby Billings Farm & Museum is a must-visit, offering everything from sleigh rides to interactive exhibits about Vermont’s agricultural history. Whether you’re exploring the town or taking in the serene snowy landscapes, there’s a sense of timeless charm that makes Woodstock unforgettable.

Woodstock in winter is a destination that feels both elegant and down-to-earth, a perfect blend of refined experiences and cozy comforts. Whether you’re savoring a gourmet meal at the Red Rooster, curling up by the fire at the Woodstock Inn, or strolling through the town’s snow-dusted streets, every moment feels special. And while the backdrop of this charming town was undoubtedly stunning, I’d like to think my outfit — a classic mix of faux fur and tartan — added its own little touch of sophistication to the scene. If you’re looking for a winter getaway that feels straight out of a postcard, Woodstock, Vermont, should be at the top of your list.

Love from Vermont,
Katie

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