Unearth The Voyage
When snow blankets Vermont’s rolling hills, one town stands out as the perfect winter getaway destination. Woodstock captures everything magical about a New England winter with its historic charm, outdoor adventures, and cozy atmosphere. Picture yourself strolling past covered bridges, sipping hot cocoa after a day on the slopes, and discovering why this village has enchanted visitors for generations.
1. Walkable Village with Serious Pedigree
Woodstock’s compact downtown feels like stepping into a Norman Rockwell painting brought to life. The village green anchors everything, surrounded by beautifully preserved 19th-century buildings that house charming shops and cafes.
Snow-covered sidewalks connect every attraction within easy walking distance, making it simple to explore without constantly jumping in and out of your car. The entire area sits within the Woodstock Village Historic District, ensuring authentic architectural details at every turn.
Winter transforms the already picturesque streets into something truly magical, with twinkling lights reflecting off fresh powder and smoke curling from chimneys throughout the neighborhood.
2. Holiday Magic at Wassail Weekend
Every December, Woodstock transforms into a Victorian wonderland during its famous Wassail Weekend celebration. The 2024 event marked the 40th anniversary of this beloved tradition, featuring horse-drawn carriage rides, costumed carolers, and townspeople dressed in period clothing.
Main Street comes alive with live music performances, traditional wassail tastings, and a charming parade that feels straight out of a Charles Dickens novel. Local merchants open their doors with special holiday treats and warm beverages for visitors.
The entire community participates in creating an authentic small-town winter festival that captures the true spirit of New England hospitality and holiday cheer.
3. Covered Bridge Postcards Right in Town
The Middle Covered Bridge sits just steps from Woodstock’s village green, creating the quintessential Vermont photo opportunity. This historic span looks especially stunning framed against winter’s white backdrop, with icicles hanging from its weathered wooden beams.
Beyond the main bridge, Woodstock offers additional covered spans at Taftsville and West Woodstock, perfect for creating your own scenic driving loop. Each bridge tells a different story of Vermont’s engineering heritage while providing shelter from winter winds.
These architectural treasures become even more photogenic when snow outlines every board and beam, making them irresistible subjects for holiday cards and social media posts.
4. A Beloved Local Ski Hill
Just five miles from downtown Woodstock, Saskadena Six offers intimate skiing that feels worlds away from crowded mega-resorts. Recently renamed from its former moniker, this family-friendly mountain specializes in creating perfect conditions for beginners and casual skiers.
The historic slopes provide enough variety to keep things interesting without overwhelming newer skiers with intimidating terrain. Lift lines stay manageable, and the atmosphere remains relaxed and welcoming throughout the winter season.
After a morning on the mountain, the short drive back to Woodstock’s restaurants and shops makes this an ideal combination for a perfect winter day in Vermont.
5. Miles of Groomed Nordic Trails
The Woodstock Inn & Resort Nordic Center maintains over twelve miles of perfectly groomed trails winding through the stunning Marsh-Billings-Rockefeller National Historical Park. These former carriage roads create gentle, scenic routes perfect for both cross-country skiing and snowshoeing adventures.
Trail conditions receive daily attention from professional groomers, ensuring consistently excellent skiing throughout the winter season. The varied terrain accommodates everyone from first-time Nordic skiers to experienced athletes seeking a good workout.
Surrounded by pristine forest and historical landmarks, these trails offer a peaceful escape into Vermont’s winter wilderness while remaining easily accessible from the village center.
6. Working Farm Fun Indoors and Out
Billings Farm & Museum brings Vermont’s agricultural heritage to life year-round, with special winter programming that delights families seeking authentic rural experiences. Heritage breed animals provide entertainment and education, while indoor exhibits offer warmth during the coldest days.
Seasonal horse-drawn sleigh rides create unforgettable memories as you glide through snow-covered fields listening to jingling harness bells. Interactive demonstrations show how Vermont farmers historically survived harsh winters using traditional methods and ingenuity.
The museum’s hands-on approach helps children understand farm life while adults appreciate the historical significance of Vermont’s agricultural traditions and their connection to modern sustainable farming practices.
7. Cheese and Maple Tastings Year-Round
Sugarbush Farm sits just minutes from Woodstock’s center, offering free tastings of authentic Vermont cheeses and maple syrup in a genuine working farm setting. The rustic country store welcomes visitors daily with samples of aged cheddars, creamy goat cheeses, and pure maple products.
Self-guided exhibits explain traditional cheese-making and maple sugaring processes, perfect for learning about Vermont’s most famous agricultural products. Winter visits provide cozy indoor warmth while showcasing how these artisanal foods develop their distinctive flavors.
The farm’s laid-back atmosphere encourages lingering over tastings while browsing locally-made gifts and treats that capture the authentic taste of Vermont’s countryside.
8. Stay Where Everything’s at Your Doorstep
The Woodstock Inn & Resort serves as the perfect home base, placing guests within walking distance of every village attraction while providing luxurious amenities and services. This historic property anchors downtown Woodstock with elegant accommodations that blend traditional New England charm with modern comforts.
Resort amenities include direct access to the Nordic trail system, spa services, and multiple dining options without leaving the property. Complimentary shuttle service connects guests to Saskadena Six for convenient ski access.
The inn’s central location eliminates the need for constant driving while ensuring easy access to Woodstock’s shops, restaurants, and attractions throughout your winter escape.
