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Family Skiing

Check out these holiday events in vintage ski towns

By Joan WallenDecember 7, 2019

North Conway, N.H. will be lit up for the holidays. (MWV Chamber)

There is no better way to get in the holiday spirit than to visit a quintessential New England town in December. 

One such community is Woodstock, Vt. Nestled in the Green Mountains just 2½ hours from Boston, three hours from Montreal and four from New York City, the town offers pure charm in all seasons, but none as much as the approaching holidays. 

Twinkling lights on trees lining the sidewalks and on greenery around shop windows, the pure white of snowbanks and snow-covered lawns, Christmas music, hot cocoa or cider and delicious baked goods as well and farm-to-table meals near a crackling fire can all be found while strolling through the village.

Highlighting the season is Wassail Weekend, set this year for Dec. 13-15. The weekend is packed with activities. House tours and holiday tales, artisan markets and performances are just some of the special events you’ll find here. 

On Friday, the weekend kicks off with the 35th annual Wassail Weekend. Shop the village stores decorated with twinkling and glowing garlands featuring practical and unique gifts. At the edge of town, Billings Farm and Museum presents Christmas at the Farm. Tour the authentically decorated farmhouse, visit the dairy farm and meet the dairy herd, draft horses, sheep and oxen. Check out exhibits of farm life and the museum highlights of New England life, including ice harvesting and maple sugaring. There will be candle dipping and ornament making, cooking demonstrations, tastings, storytelling, plus horse-drawn sleigh or wagon rides on Sunday. After storytelling at the public library in town, cap off the evening with a live concert by the Whiffenpoofs, Yale University’s acclaimed a cappella singers, at the Town Hall theater.

On Saturday, kids can start off with a breakfast with Santa at the quaint Little Theatre. For the 18th year, the Holiday House Tour will take place from 9:30 a.m. to 2 p.m. A horse-drawn wagon will transport visitors around town for indoor and outdoor tours of some of the most charming village homes decorated traditionally for the holidays. 

The Wassail Parade, as old as the weekend celebration, brings out children and adults sporting historical Christmas finery while riding horses of all sizes, from the smallest ponies to the largest Percherons. The majestic animals, colorful outfits, jingling bells amid the backdrop of this picture-book village is truly magic. Yule log and tree lighting followed by a choice of a cappella concerts round out the afternoon celebrations. If you’re not tired yet, the Woodstock Inn offers a Wassail Feast Saturday night that can be followed up by two different performances of Celtic holiday music. 

Sunday offers the final day for one-of-a-kind shopping at the Holiday Fair at the Masonic Lodge. In the afternoon there’s cookies with Santa and a showing of the film “The Grinch.” The weekend concludes with a Community Sing featuring professional musicians, with the audience joining in, performing portions of Handel’s Messiah.

While you’re in the area, take some turns at the local ski area, Suicide Six, perfect for beginners and families while challenging for experts and hot shots. The snowsports school, one of the oldest in the country, boasts world-class instructors for both skiing and snowboarding. Perley’s Pourhouse in the base lodge offers table service in the restaurant, lounge and bar with hearty fare, a children’s menu and local brews. For a fine dining experience, head into  Woodstock Village and enjoy farm-to-table fare at the Woodstock Inn’s Red Rooster. Or for a more casual meal, try the fondue and craft beer by the fireside at Richardson’s Tavern. 

If you have time and are looking for some terrain with more trails and elevation, travel down the road a ways to Killington or Okemo. Both also offer holiday activities for the entire family.

Across the border, the Mount Washington Valley, which covers a wide area on the eastern slope of the White Mountains in New Hampshire, offers up some unique activities for the holiday season in several of its towns. If you purchase a lodging package in the valley on Dec. 14-15, you can join the Inn to Inn Cookie Tour. As you travel from Fryeburg, Maine, to Eaton and Albany, N.H., then through North Conway and up to Bartlett and Jackson, you’ll be savoring delicious treats, seeing stunning decorated trees and coming across plenty of hidden treasures. This annual event is always a sellout and crowd pleaser. 

The famed big-band sounds of the Glen Miller Orchestra will entertain you in Bretton Woods at the Omni Mount Washington Hotel on Dec. 10. You can enjoy fine dining and dance the night away while enjoying the golden age of dance music with this renowned band, which will be playing special arrangements of traditional holiday music to get you “In The Mood,” the theme of this performance.

Bring the kids and take a “Journey to the North Pole” on the Conway Scenic Railroad, departing from North Conway Dec. 20-23. Upon arriving at the North Pole, Santa’s elves will escort you to the North Pole Theatre for a magical, dramatic reading and visit from Santa. A special gift awaits each child on the return trip from this enchanted two-hour adventure.

The village of Jackson is another picturesque mountain town that twinkles during the holiday season with an annual tree lighting ceremony, the Jingle Chocolate Tour and more. Nestlenook Farm Resort joins the Jackson Chamber of Commerce in presenting this tour Dec. 7-8. You will board an Austrian horse-drawn sleigh at the gazebo at Nestlenook and begin an hourlong tour through Jackson Village. At each of eight local businesses, you’ll be treated to homemade chocolate delicacies to enjoy on the spot or to save in a holiday bag for future enjoyment.

While in the area you’ll be able to get in some wonderful skiing at the local resorts. King Pine, Cranmore, Wildcat, Attitash, Black Mountain and Bretton Woods are conveniently located. For cross-country buffs, there’s Jackson Ski Touring, Great Glen Trails and the nordic center at Bretton Woods. In addition, there’s dining for all tastes and pocketbooks, from family fare to local brewpubs to fine dining in all the towns comprising the Mount Washington Valley.

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Tags: family skiing, holiday events, Jackson, North Conway, Woodstock

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