Winters in Rowayton
📍 Rowayton, CT

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Sweater || Jeans || Wool Coat || Chelsea Boots || Tote Bag

There’s something undeniably magical about coastal towns in the winter. The summer crowds have long since departed, leaving behind a peaceful charm that feels both cozy and refreshing. Rowayton, Connecticut, is no exception. Just a short drive from New York City, this quaint waterfront town is the perfect destination for a quiet winter escape. From charming cafés to picturesque streets lined with historic homes, spending a winter’s day in Rowayton is the ideal way to embrace the season’s slower pace.

Morning Coffee at Arden’s

Every perfect winter day should start with a warm cup of coffee, and in Rowayton, that means stopping by Arden’s. Tucked in the heart of town, this inviting café is known for its high-quality coffee, delicious pastries, and cozy atmosphere. On chilly mornings, there’s nothing better than wrapping your hands around a steaming latte and savoring a freshly baked croissant while watching the water just outside. Whether you prefer a classic cappuccino or a cozy seasonal latte, Arden’s is a must-visit for a caffeine fix before exploring the town.

Walking Through the Neighborhood

One of my favorite things about Rowayton is simply walking through its charming streets. Even in the winter, the beauty of the town shines through. Historic New England homes, each with their own character and charm, line the streets, some adorned with subtle seasonal décor. A stroll along the waterfront offers stunning views of the Five Mile River, with the crisp winter air adding a refreshing touch. Bundle up in a warm coat and take it slow—this is the kind of place that invites you to linger, take in the surroundings, and appreciate the timeless charm of a classic New England town.

Lunch at Rowayton Seafood

After a leisurely walk, there’s no better way to warm up than with a cozy meal at Rowayton Seafood. This waterfront staple is known for its fresh seafood and inviting atmosphere, and in the winter, their heated patio makes for a perfect dining spot. There’s something so special about enjoying a warm bowl of their legendary New England clam chowder while overlooking the marina, the boats gently bobbing in the water. Pair it with a lobster roll or a simple plate of oysters, and you have a quintessential Rowayton dining experience. Whether you sit indoors or brave the crisp air outside, the setting is effortlessly charming and undeniably New England.

There’s a quiet beauty to Rowayton in the winter—a sense of calm that invites you to slow down and appreciate the little things. Whether it’s sipping coffee at Arden’s, browsing the shelves at Rowayton Market, taking a peaceful waterfront walk, or indulging in a delicious meal at Rowayton Seafood, the town offers a perfect blend of charm and comfort. If you’re looking for a winter escape that’s both scenic and serene, Rowayton is well worth a visit.

Love from Connecticut,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.

Winter in Woodstock
📍 Woodstock, Vermont

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Dress || Jacket (Similar) || Heels || Similar Handbag || Tights || Earrings

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

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.

Après-Ski Inspired Style
📍 Stowe, Vermont

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Jacket (Similar) || Turtleneck || Jeans || Boots || Similar Handbag || Beanie

Confession time: I don’t ski. Not even a little. While others are gracefully carving down the slopes, I’m the one sipping hot cocoa by the fire, perfectly content in my cozy layers. Honestly, I think I’d spend more time on the ground than upright if I tried. But here’s the thing: you don’t have to ski to embrace the effortless, chic style that comes with an alpine getaway. The refined elegance of après-ski style is all about staying warm, comfortable, and looking put-together—whether you’re in the Alps or a snowy Vermont village like I recently visited.

The beauty of après-ski style lies in its versatility. With a few thoughtful wardrobe staples, you can easily channel the polished, cozy vibe that feels just as at home in a ski lodge as it does strolling through a snowy town. Here are my essentials for nailing the look:

Plush Faux Fur Outerwear

Nothing says alpine chic quite like a statement faux fur jacket. Not only does it provide warmth on those crisp winter days, but it also instantly elevates your outfit. I’m partial to a sleek black or deep brown faux fur coat, like the one I wore during my Vermont trip. It’s versatile enough to pair with anything—from jeans to tailored pants—and the soft texture gives off a luxurious, cozy vibe. Plus, a well-chosen coat can turn even the simplest outfit into a winter fashion moment. Whether you’re heading out for a coffee run or posing for photos in front of a snow-dusted chalet, a plush coat is a must.

Cashmere Sweaters

A quality cashmere sweater is one of the most versatile pieces you can pack for a winter getaway. Lightweight yet incredibly warm, cashmere is perfect for layering under coats or wearing on its own indoors. Neutral tones like camel, ivory, and gray are timeless and easy to style, but don’t shy away from a pop of color if it suits your mood. What I love most about cashmere is how it feels against the skin—soft, breathable, and never bulky. It’s ideal for those cozy moments by the fireplace or paired with tailored trousers for an effortlessly sophisticated look.

Tailored Pants or Denim

When it comes to bottoms, tailored pants or high-waisted black denim are my go-to options. They’re comfortable enough for all-day wear yet polished enough to transition seamlessly into the evening. For my Vermont trip, I opted for sleek black denim, which worked beautifully with my faux fur jacket and cashmere layers. The key is to choose pieces that fit well and have a bit of structure—nothing too slouchy or oversized. Bonus points if they’re slightly cropped to show off your winter boots!

Stylish Winter Boots

Speaking of boots, finding the perfect pair is essential for après-ski style. Look for a pair that combines practicality with elegance, like sleek leather or suede Chelsea boots with a sturdy sole. During my trip, I relied on my Margaux Chelsea boots, which offered both comfort and sophistication. They’re waterproof (a must for snowy conditions) and versatile enough to wear with everything from jeans to dresses. A chic pair of boots can tie your entire outfit together while keeping your feet warm and dry.

Wool or Cashmere Accessories

No winter outfit is complete without the right accessories. Wool or cashmere beanies, scarves, and gloves not only keep you cozy but also add an extra layer of texture and sophistication to your look. I’m a fan of neutral accessories that complement the rest of my outfit, but you could also use this as an opportunity to play with patterns or subtle embellishments. A well-chosen scarf, for example, can double as a shawl indoors, while a classic beanie keeps you looking effortlessly cool on a snowy day.

Elevated Base Layers

Base layers don’t have to be boring! Opt for pieces made from merino wool or other breathable fabrics that keep you warm without adding bulk. I love a slim-fitting turtleneck in a neutral color, which works beautifully as a standalone piece or as a layer under heavier sweaters and jackets. These elevated basics are the unsung heroes of après-ski style—you may not see them, but they’re doing all the heavy lifting when it comes to staying warm and stylish.

Statement Sunglasses

Don’t underestimate the power of a good pair of sunglasses—even in the snow. The glare from the sun reflecting off the white landscape can be intense, making sunglasses a practical necessity. But they’re also a fantastic way to add a touch of glamour to your outfit. Oversized frames or aviators are my top picks for a classic, polished look. Plus, they’re perfect for those sunny, snow-covered strolls through the village.

Sleek Base Outfit for Dining

After a day out in the cold, there’s nothing better than warming up with a cozy meal in a beautiful setting. For evenings out, I love to pack a sleek base outfit that can easily be dressed up or down. A sweater dress or a chic trousers-and-top combo works perfectly. These pieces are comfortable enough for lingering over dinner yet polished enough to feel put-together. Add a pair of statement earrings or a bold lip color, and you’re ready to enjoy a refined après-ski dinner.

Whether you’re sipping mulled wine by the fire or wandering through a picturesque ski town, après-ski style is all about combining comfort and elegance. You don’t have to hit the slopes to embrace this cozy, chic aesthetic—just a few thoughtfully chosen pieces will have you looking the part. So grab your faux fur coat, your cashmere layers, and your favorite pair of boots, and let the snowy adventures begin!

Love from Vermont,
Katie

Thanks for stopping by! To keep up with all things about my travels and style, be sure to visit throughout the week! Be sure to check out my exclusive adventures in NYC and New England.