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Woodstock Inn - Family Ski Weekend in Vermont

Our mission: a winter vacation with something for everyone in the family. Our destination: Woodstock, Vermont, easy to reach off I89.

If you have driven Vermont’s swerving but scenic Route 4, along the Ottaquechee River, you have passed through the charming town of Woodstock, lined with historic mansions and anchored by The Woodstock Inn.

The Woodstock Inn’s roaring 20-foot stone fireplace provided instant warmth as we entered the lobby, and gleaned a bit of the bold thinking of the 1969 hotel’s founder, Laurence S. Rockefeller (yes, the name should sound familiar). Our room was tastefully furnished, with a gleaming white marble bathroom and one of the comfiest four-poster beds I have ever encountered.

The Woodstock Ski Weekend package for our family included lodging, breakfast, ski tickets for Downhill skiing at Suicide Six and Nordic trail passes, plus use of the Health and Fitness Center – all of which are owned and operated by the Inn, originally amassed by Rockefeller and his wife, Mary Billings-French.

The Woodstock Inn, and the expansive resort property, is just a fraction of the Rockefellers’ area acquisitions, part of their national environmental conservation. The Rockefeller legacy is easily witnessed in Woodstock from their reforestation efforts (after “Wood-stock” had been stripped of trees in the 1800’s), to Billings Farm, the Rockefeller’s ancestral home, and 550-acres, all preserved as Vermont’s first National park, the Marsh-Billings-Rockefeller National Historical Park.

I explained this significance to our kids over breakfast, while they devoured fluffy waffles drenched in requisite Vermont maple syrup.

Then we drove four pastoral miles through the Vermont river valley, by aging barns, grazing horses and cows, and a quirky Country Store, to the legendary snow-covered slopes of Suicide Six. The local lore surrounding this ski area stretches back to America’s first ski lift, a rope tow powered by a Model T in 1934. In 1936, Bunny Bertram moved his ski operation to adjacent topographical Hill No. 6, which some said was too steep to ski – even “Suicidal” – hence the name.

By today’s standards (and with today’s equipment), Suicide Six is not so intimidating. In fact, the 23 trails served by two-double chairs and a handle-tow are family-friendly and tame compared to nearby Killington, Pico, and Okemo Mountains. We found the skiing at “Six” to be refreshingly fun. The fireplaced base lodge is cheery and neat, with a sunny slope-facing restaurant. The ski club (the oldest in America) and the staff (Woodstock Inn-managed) are like an extended ski family. The 650’ vertical hill offers a decently pitched face, and some meandering cruisers around the sides - mostly covered in well-groomed, man-made snow.

Nordic skiing was also on our family-fun list, so after carving a dozen or so “Suicide” runs, we decided to try some cross-country sliding. Woodstock’s Country Club, a half a mile behind the Inn, gives winter adventurers over 60-kilometers of groomed trails on the Golf Course, and the hilly Mount Peg and Mount Tom - all inclusive to Woodstock Inn package guests. Snowshoeing is recommended for climbing to the scenic summit of Mount Tom, along the century old carriage roads.

After all this snow fun, we were rosy cheeked and ready to soak in the impressive Health Club and Fitness Center, a mile beyond the Country Club. This 41,000-square foot indoor center has an Olympic-size pool and hot tub, sauna and steam room, fitness equipment with exercise classes, indoor tennis, racquetball, squash, and a full-service spa.

We returned to the Inn for freshly baked cookies served at traditional Tea Time. Then my teenage daughter and I strolled downtown Woodstock as the sun set over the beautiful brick buildings. We browsed a dozen establishments, from cluttered country stores to chic art boutiques. She made me promise to return to Woodstock for prom dress shopping at the vintage dress shop – always thinking about her next fashion gig. My son’s interest in architecture had him touring the historic district with a more intellectual eye, while Greg took photos of the incredibly quaint settlement that dates back to 1761.

That evening, our dinner in the Woodstock Inn’s elegant dining room was exquisitely prepared and delicious. The pianist lightened our otherwise formal fare; we played a friendly round of name that tune.

Later, Greg and I kicked back in wingbacks at the Inn’s Tavern where a lively jazz trio entertained. This cozy Richardson’s Tavern is a replica of the first watering hole and lodge of Woodstock that occupied this spot in 1793. It now serves as an inviting alternative if you prefer pub fare.

Sunday morning we roused early, and meandered 20-minutes along Route 4 to Killington’s Skyeship gondola for a few hours of more extensive skiing on the east’s most sprawling ski resort. Returning through Woodstock later that day, we waved fond farewell to The Woodstock Inn and Resort, the centerpiece of the charming namesake town.  

It was mission accomplished for our family. Even our hard-to-please princess, with her passion for shopping and sleeping in sumptuous surroundings, was smiling. Our energizer son had his fill of outdoor adventure in the Vermont winter-scape. Greg found Woodstock and the surrounding hills and mountains to be photogenic gems. I loved the dose of education on vacation, tracing the wealthy but well-intentioned Rockefellers. But I am not all about philanthropy; my cravings for posh 4-star lodging and entertainment were met too.

Destinations l New England l Rockies l Canada l Europe

All Stories by Heather Burke All Photography by Greg Burke

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