A long weekend in the heart of the Green Mountains offers the quintessential New England winter experience, combining the refined charm of Woodstock with the high-energy excitement of Killington, “The Beast of the East.” Jason Snyder of Maine suggests the itinerary below that blends cross-country serenity and a historic town center with formidable downhill challenges, ensuring a memorable escape.
The Charm of Woodstock, Vermont
Woodstock, often called the “prettiest small town in America,” is the embodiment of classic New England aesthetics: a covered bridge at the center of town, a pristine village green, and beautifully preserved Georgian and Federal architecture. It’s the perfect, sophisticated base for a relaxed start to the weekend.
Arrival and First Impressions
Arriving in Woodstock sets a tone of tranquility. The town feels worlds away from the hustle of modern life. Settle into accommodations that range from cozy B&Bs to the luxurious Woodstock Inn & Resort. The Inn, a landmark since 1892, offers impeccable service, a world-class spa, and is centrally located for exploring the town on foot.
Day 1: Cross-Country Skiing and Covered Bridges
Rather than diving straight into the high-octane environment of Killington, the first day is dedicated to embracing Woodstock’s peaceful winter landscape.
• Morning: Gentle Glides at the Nordic Center
The Woodstock Nordic Center, operated by the Woodstock Inn, boasts over 30 kilometers of meticulously groomed trails that wind through the town’s golf course and along the scenic Kedron Valley. The trails are varied enough for both beginners and experienced cross-country skiers, offering a peaceful way to acclimate to the mountain air. The quiet glide through snow-laden forests is a meditative experience, often punctuated by views of the Ottauquechee River.
• Lunch in Town
After a brisk morning, head back into the village for a warm, hearty lunch. Local favorites like The Daily Catch Woodstock provide New England seafood classics in a cozy setting.
• Afternoon: Historic Exploration and the Village Center
Spend the afternoon exploring the town’s center. Walk across the iconic Middle Covered Bridge. A visit to the Billings Farm & Museum is a must. Operating as a working dairy farm and a museum of Vermont’s rural history, it offers a fascinating glimpse into 19th-century farm life. In winter, visitors can enjoy sleigh rides, meet the Jersey cows, and sample their famous cheddar cheese.
• Evening: Fine Dining and Relaxation
Woodstock excels at sophisticated dining. For an elegant dinner, The Prince & The Pauper Restaurant has been a local institution for over 40 years, serving French-American cuisine in a charming, intimate setting. After dinner, a quiet evening by a fire in the Inn’s lobby or a local pub like the Woodstock Inn’s Red Rooster Bar provides the perfect end to a relaxed day.
The Thrill of Killington, Vermont
Day two and three shift gears dramatically. Just a 30-minute drive north, Killington is a different world. It’s the largest ski resort in the East by acreage and snowfall, famous for its lively atmosphere, extensive terrain, and an infamous aprés-ski scene.
Day 2: Conquering “The Beast”
• Morning: First Tracks at Killington
Arrive early at the mountain. Killington is vast, spread across six interconnected mountain peaks plus the standalone Pico Mountain. To maximize a day here, it’s best to have a plan. The resort offers nearly 1,500 acres of skiable terrain.
Start at the K-1 Base Lodge to get onto the mountain quickly. The Snowdon area offers great blue and green runs for a warm-up, while the Canyon area is home to steeper, more challenging terrain.
• Lunch On the Mountain
For lunch, the options are numerous. The Peak Lodge, accessible via the K-1 gondola, offers a sit-down dining experience with panoramic views of the surrounding mountains and, on a clear day, as far as the Adirondacks. It’s a step up from typical lodge fare.
• Afternoon: Exploring the Different Peaks
Work your way across the different peaks. Bear Mountain is known for its challenging bumps and the famous “Outer Limits” trail, a double-black diamond mogul run that tests even expert skiers. For those seeking groomers, the long, winding trails like “Great Eastern” offer miles of cruising. The interconnecting trail system makes exploration an adventure in itself.
• Evening: The Aprés-Ski Scene
The day on the slopes transitions seamlessly into the legendary aprés-ski scene. The access road leading to Killington is lined with bars and restaurants.
The Wobbly Barn Steakhouse is an institution. It’s a restaurant, a bar, and a nightclub all in one. The massive, rustic barn structure serves excellent steaks and seafood, but the real draw is the late-night atmosphere with live music and dancing that often goes into the early hours. For something more casual, Casey’s Caboose offers a fun, train car-themed environment with great pub food.
Day 3: A Balanced Finale
The final day balances the high energy of Killington with a last taste of Woodstock’s charm before heading home.
• Morning: Final Runs or Spa Day
Depending on energy levels, the morning can be spent in one of two ways.
Option A: Head back to Killington for a few final runs, perhaps exploring Pico Mountain, which is quieter and offers a more laid-back experience.
Option B: Stay in Woodstock and treat tired muscles to a spa day. The Woodstock Inn & Resort Spa offers a range of treatments, from deep tissue massages to revitalizing facials, in a serene, modern setting.
• Lunch: A Casual Fare
A casual lunch back in Woodstock at the Woodstock Public House provides comfort food like burgers and mac and cheese, perfect fuel for the journey home.
• Afternoon: Departure with a Sweet Stop
Before leaving the area, make a stop at the Sugarbush Cheese & Maple Farm. It’s a short drive from Woodstock and offers tours of a maple sugar house (with free samples of different grades of syrup) and a chance to watch cheese making. It’s the perfect spot to pick up authentic Vermont souvenirs and a delicious, sweet end to the trip.
This long weekend itinerary offers a perfect duality: the quiet sophistication and pastoral beauty of Woodstock paired with the expansive terrain and vibrant energy of Killington. It’s a tailored experience that showcases the very best of winter in the Green Mountain State.