A Perfect Weekend: Woodstock in Winter

Every Vermont skier should make a pilgrimage to Woodstock where lift-served skiing was born. The local ski area, Saskadena Six (formerly Suicide Six), traces its heritage back to 1934 when the first rope tow in the U.S.  was set up in a farmer’s field.

A perfect day starts with snow. Light, cold flakes fall through the night. By morning, the trees are blanketed. You rise early, down a cup of coffee and head out.

But even assuming you ski bell to bell, that’s only part of a ski day or weekend. Half of the weekend is what you do after you leave the mountain; where you eat, where you stay. We put together  a classic Vermont weekend – from all-out luxe at historic inns to more budget-friendly options.

The “splurge” options below add up to round $1500 for a day of skiing, a night of lodging, massage, food and beverages for two, while the “save” options come to about $500 all- nclusive.


Today, much of the town of Woodstock looks nearly the same as it might have 100 years ago.  Colonial and red brick buildings line the main street and the stately The Woodstock Inn, once owned by Laurance Rockefeller, presides over the green.

The inn, its Saskadena 6 alpine ski hill and its cross-country touring center are all part of the Woodstock Foundation, set up by the Rockefellers and dedicated to preserving the town’s sense of community and genteel history.  The cross country trails (shown above, Mount Tom) are extensive and perfectly manicured, with rentals available at the inn’s nordic center. Many of the inn’s rooms and suites are individually designed and reflect local history. One is patterned after Laurance Rockefeller’s study, another after his wife Mary’s bedroom.

One of the inn’s legacy suites is modeled after former owner’s Mary Laurance Rockefeller’s room. Courtesy photo.

Those suites go for upwards of $1,000 a night. But you can save on a splurge weekend by booking a two-night Sip and Stay package, which includes a room (rates start at $457 midweek) and two lift tickets to Saskadena 6. Through the end of March 2024, you also get a $50 credit toward food or drinks.

Open Wednesdays through Sundays until mid-March, Saskadena 6 remains one of Vermont’s hidden gems: a mid-sized mountain with few crowds, great grooming and steeps that earned the hill its original name: Suicide 6. Spend the day arcing turns before getting lunch at Perley’s Pourhouse at the base.


In the afternoon, check into the Woodstock Inn’s spa, leaving enough time to relax in the outdoor whirlpool, the eucalyptus steam room or dry-cedar sauna. Feeling decadent? Book the $300, 100-minute Signature Experience, an exfoliating scrub and hydrating body wrap followed by a full-body massage.

After, wander into town to browse shops that range from Ferro Custom Jewelers for estate jewelry to Vermont-made Danforth Pewter. Stop in for a craft cocktail at the Au Comptoir cocktail bar but head back to The Woodstock Inn for dinner.

The inn’s executive chef, Matthew McClure is a seven-time finalist for the James Beard Foundation’s regional “Best Chef” award and works with seasonal produce (including what’s grown in the inn’s own Kelly Way gardens) to prepare dishes such as maple-cured cod with eggplant caponata and couscous.


Though much of Woodstock feels both Vermont-elegant and old-world pricey, it doesn’t have to be. Daily lift tickets at Saskadena 6 are $59, Wednesdays through Fridays and go as high as $99 on holiday weekends. For a $35 trail pass (weekends) you can also explore the more than 45 kilometers of Nordic trails that leave right from the center of town and snake through the Mt. Tom area and the Marsh Billings Rockefeller National Historic Park. On some winter weekends there are torchlit snowshoe hikes ($12) through the park with s’mores around a campfire and the park has free loaner snowshoes, on a first-come basis. On certain winter dates, sleigh rides ($5 per person) also run through the park.

In town, some of the descendants of the Billings (for whom the park is named) still run F.H. Gillingham & Sons, a classic general store that has been in the same family since 1886 and has all sorts of memorabilia. Stop in there before heading to Worthy Kitchen for one of their renowned burgers. If you were able to get a reservation at Cloudland Farm – a working farm that serves family-style dinners on Fridays and Saturdays — the $63 three-course dinner is a treat.  After, fall into a four-poster bed at The Shire, where river-front rooms go for $135 to $232, depending on the night.

Lisa Lynn

Editor of VT SKI + RIDE and Vermont Sports.