Escaping NYC: A Weekend Guide to Central Vermont’s Best-Kept Secrets

A winter ski weekend or week in Vermont begins with one destination: Killington Resort. Known as “The Beast of the East,” Killington offers the largest ski area in the Eastern United States, attracting everyone from first-time skiers to seasoned experts. Twenty minutes away from The Cobble House, the resort offers extensive terrain, modern lifts, and some of the longest ski seasons in the Northeast. 

Killington’s diverse trails ensure that every member of your group finds a run suited to their ability level. Start your Saturday morning with our complimentary ‘First breakfast’ before making the scenic drive from The Cobble House  to Killington, or we can arrange private transportation for you. 

For guests looking to skills maxx on the mountain, private ski lessons offer personalized instruction tailored to individual goals. Whether you’re refining your carving technique, tackling steeper terrain, or learning to ski for the first time, private instruction moves you forward faster and provides an elevated experience. 

Sometimes the perfect Vermont weekend involves slowing down rather than speeding up and Vermont is very good at that.  For those seeking wellness and restoration, Central Vermont offers exceptional opportunities to unwind.

We suggest you begin Friday afternoon by exploring our neighbor, the town of Woodstock which has one of New England’s most picturesque village centers.  Stroll through locally owned boutiques, art galleries, and specialty shops before heading to Kelly Way Gardens.  Cared for by the Woodstock Inn & Resort, the gardens showcase Vermont’s agricultural heritage and provide a beautiful setting for an afternoon walk.  Afterwards, the Woodstock Inn offers five dining options ranging from fine dining at Red Rooster to the more casual Richardson’s Tavern. These are beloved, in-demand eateries, so reservations are highly recommended. Come home, put your feet up in the Reading Room. 

Dedicate your Saturday entirely to pampering. Take a gorgeous drive north through the countryside to The Spa at Essex Resort, one of Vermont’s premier spa destinations. Just over an hour, the journey is part of the experience. Vermont couldn’t be prettier. 

Dedicate your Saturday entirely to pampering. Take a gorgeous drive north through the countryside to The Spa at Essex Resort, one of Vermont’s premier spa destinations. Just over an hour, the journey is part of the experience. Vermont couldn’t be prettier. 

The Spa at Essex offers day passes that allow visitors to enjoy spa amenities while selecting treatments that suit their individual needs. Guests can create a customized wellness day that may include massage therapy, facials, body scrubs, aromatherapy treatments, and restorative wellness services.

Popular treatments include deep-tissue massages designed to relieve stress and muscle tension, hydrating facials that rejuvenate skin, and signature body therapies inspired by Vermont’s natural environment. Whether indulging as a couple, a group, or enjoying a solo retreat, the spa provides a luxurious environment focused on relaxation and renewal.

Following a day of pampering, return to The Cobble House and continue your designed Vermont experience with one of the most memorable additions to a weekend, a dinner or brunch specially prepared by a private chef.

Rather than rushing to restaurant reservations, our guests can enjoy a beautifully prepared meal within the comfort of their vacation home. The dining room, gourmet kitchen, and elegant gathering spaces at The Cobble House are ideal settings for memorable evenings and culinary experiences. Vermont’s culinary talent shines through customized menus featuring local produce, artisanal cheeses, seasonal ingredients, and farm-fresh ingredients with extraordinary flavours.

The combination of scenic countryside, luxury spa treatments, private dining, and well appointed accommodations creates a restorative weekend worlds away from the grind of the City.

In the Fall, Vermont’s crisp, juicy apples rain from the trees. No wonder Vermont has 15 plus cideries producing a variety of delicious hard ciders for every palate. Wonderful on their own, they are a refreshing alternative to beer or sparkling wine, and they make an excellent cocktail ingredient.

Create your own foodie weekend exploring a delicious culinary trail.  Make a weekend of choosing a Cheddar made right here in Vermont – there’s even a  Vermont Cheese Trail. You could even build a weekend following a taste tour of Vermont’s velvety legend the Creemee when in summer season.  Check these articles from Food & Wine and Boston Magazine to plot your Creemee Crawl comparison tour.

Enhance your experience by arranging a concierge chauffeur for the weekend. With transportation handled professionally, guests can focus entirely on enjoying Vermont’s wineries, tasting rooms, and culinary destinations. Note to New Yorkers: There are limited Uber type services outside of the Burlington area but we are happy to introduce you to local car services.

Enhance your experience by arranging a concierge chauffeur for the weekend. With transportation handled professionally, guests can focus entirely on enjoying Vermont’s wineries, tasting rooms, and culinary destinations. Note to New Yorkers: There are limited Uber type services outside of the Burlington area but we are happy to introduce you to local car services. 

Begin your culinary adventure with friends of ours at Domaine La Garagista’s Bar No’Ella Caviste & Cafe in Barnard. Widely regarded as one of Vermont’s most innovative natural wine producers, La Garagista showcases wines crafted from cold-climate grape varieties and regenerative farming practices. The tasting room offers visitors an intimate introduction to Vermont’s emerging wine culture.

After an afternoon tasting, you’ll be ready for Red Barn Dinners hosted by Kelly Way Gardens. These celebrated farm-to-table dinners highlight local farms, seasonal ingredients, and Vermont’s agricultural heritage. The communal atmosphere and exceptional cuisine make for a memorable evening. Choose from a seasonal four-course meal with wine pairings, or a three-course family-style meal, and reserve your spots early. These exclusive dinners fill up faster than spots in Manhattan. 

Dedicate Saturday to exploring Vermont vineyards and sticking close to ‘home’ at The Cobble House. Begin with a visit to Putnam Vineyard, where scenic views and carefully crafted wines provide an authentic Vermont wine-country experience.

Continue to Fable Farm, known for its biodynamic fermentation practices. They are known for their creative winemaking philosophy, ciders, vinegars and stunning setting overlooking rolling farmland. Tastings often showcase unique expressions of Vermont terroir that surprise even seasoned wine enthusiasts. Buy their lovely vinegars for making salads at home and savoring Vermont memories.

For the grand finale, reserve dinner at Twin Farms, one of the most prestigious luxury properties in the United States. Twin Farms’ dining program emphasizes extraordinary seasonal ingredients, personalized menus, and impeccable service.

Wine enthusiasts can explore the property’s extensive wine cellar, featuring exceptional domestic and international selections curated by expert sommeliers. For an even more immersive experience, inquire about Chef’s Table experiences and specialty dining enhancements that provide direct access to the culinary team.

After an exceptional evening, return to The Cobble House for a peaceful night’s sleep surrounded by the quiet beauty of Vermont’s countryside where the Milky Way regularly stuns with a silent overhead show. 

For discerning food lovers, this weekend rivals experiences found in Napa Valley or the Hudson Valley while remaining wonderfully under-the-radar.

Adventure seekers visiting Vermont in June should plan around one of the state’s most beloved annual events: the Quechee Balloon Festival.

Each June in Quechee, the festival transforms the sky into a wildly colorful display of hot-air balloons rising above the Green Mountains. Morning launches, evening glow events, local vendors, and family-friendly activities make this a magical Vermont experience for all ages.

From The Cobble House, reaching Quechee is simple: cross the Gaysville bridge and travel east on VT 107 then south on 89 to Quechee. The drive takes approximately 25 minutes and passes through some of Vermont’s most scenic countryside.

In Quechee, no visit is complete without exploring Quechee Gorge. Often called “Vermont’s Little Grand Canyon,” the gorge offers dramatic views, hiking opportunities, and excellent photography locations. The Ottauquechee River cuts through towering cliffs, creating one of the state’s most iconic natural landmarks.

After taking in the gorge, visit the Simon Pearce Flagship Location. Here, visitors can watch master artisans create hand-blown glass using traditional techniques. The live glassblowing demonstrations provide fascinating insight into the craftsmanship behind Simon Pearce’s internationally recognized products.

Continue the experience with lunch or dinner at the Simon Pearce Restaurant. Overlooking waterfalls on the Ottauquechee River, the restaurant combines the scenery with refined New England cuisine. Guests can reserve tables in the dining room or inquire about private event spaces featuring exceptional river views.