In Southern Vermont…
Grafton Ice Bar 2020
You’ll want to bundle up for this chilly outdoor event featuring a bar literally made out of ice.
Signature cocktails are served through ice sculptures at this 21-and-older event. In addition to cocktails, there will be beer and food trucks, music provided by a DJ and multiple bonfires to help you keep warm. The event runs from 4 to 8 p.m.
General admission tickets include two drink vouchers. Limited VIP tickets include two drink vouchers, early access to the event at 3 p.m., access to a warming tent, and a swag bag of ice bar and Vermont products.
Candlelight Dinner Series
Ye Olde Tavern
Jan. 14 and Feb. 11
Dine like it’s 1790!
On the second Tuesday of the month, Ye Olde Tavern turns back time and turns off the lights. Experience what it was like to dine at the tavern just as its guests did at the turn of the 18th century — with the flicker of oil lamps, the roar of the fireplaces, and the sounds of classical music and conversation.
Traditional New England comfort food and vintage cocktails make up the menu, which is served from 5 until 9 p.m. Reservations are suggested.
64th Brattleboro Winter Carnival
The Brattleboro Winter Carnival, one of the oldest ongoing winter carnivals in the country, is celebrating its 64th year. The carnival, founded in 1957 by Fred Harris, one of the first “extreme skiers” and founder of the Harris Hill Ski Jump, was modeled after festivals in Quebec, Canada, and in New Hampshire.
You won’t want to miss out on the week of fun, family-friendly activities. There’s something for everyone, from pancake breakfasts to sleigh rides and snowshoeing. Outdoor events include skating, skiing, snowmobile rides, snow sculpture contests, as well as the Junior Olympic downhill skiing and skating competitions.
Be sure to attend the popular “Sugar on Snow Party,” where you’ll be served the timeless New England treat: thick maple syrup poured over snow. Other activities include a fishing derby, chili cook-off, a variety show and more.
There’s so much to do and see at the annual WinterFest in the village of North Bennington. You can dive into the icy waters of Lake Paran during the annual Penguin Plunge or sip hot chocolate, build a snowman or enjoy a wagon ride.
Activities include a chili festival, a book sale, cookie decorating, winter crafts for children, an indoor craft fair, a children’s carnival and more.
Harris Hill Ski Jump
Feel the excitement rush through the crowd as competitors soar through the air after flying down the 90-meter Harris Hill Ski Jump. The Olympic-size venue is the only one of its size in New England and has been host to nine national championships since opening in 1922.
On Saturday, jumpers will compete in the Pepsi Challenge and U.S. Cup. The Fred Harris Memorial Tournament follows on Sunday. Gates open at 10 a.m. both days, with trial rounds at 11 a.m. Competition begins at noon on both days. Food vendors, a beer tent and event souvenirs will be available at the base of the jump.
In the Berkshires…
10×10 Upstreet Arts Festival
Where can you find new theater, art, comedy, dance and music in the middle of winter?
The 10×10 Upstreet Arts Festival celebrates all that and more over the course of 11 days with annual events such as 10 Days of Play at the Berkshire Museum, the Berkshire Art Association’s 10×10 Real Art Party and the 10×10 New Plays at Barrington Stage Company.
North Adams Winterfest
Winterfest returns to North Adams with all the usual goodness you’ve come to expect: horse-drawn carriage rides, free ice skating, ice carving, a campfire and s’mores, a winter carnival for kids, and a farmer and artisan market.
And don’t forget to bring your appetite. The annual chowder cook-off once again will have local restaurants vying for the title of “best chowder” and the coveted “people’s choice” awards.
Shakespeare’s Valentine Surprise
Shakespeare and Company
Looking for something unique to do with your valentine? Or just want a fun night out at the theater?
Celebrate the magic and folly of love at Shakespeare’s Valentine Surprise. This annual show has a different theme each year, but traditionally includes company actors presenting scenes of some of the most famous lovers of all time – with plenty of surprises mixed in. Two performances only. Tickets: $25 for adults; $10 for students.
Family Sunset Ski & S’mores
Enjoy a winter sunset at Notchview on snowshoes or skis followed by s’mores at the lodge. Sunset is expected to take place at 5:28 p.m., so be sure to arrive by 4 p.m. to get your rental equipment, afternoon ski pass and hit the trails before heading back to the lodge for 5:30 p.m. to enjoy s’mores around the bonfire. Preregistration is required. Cost is $12 for members; $20 for nonmembers; free for children. Price includes daily pass and s’mores. Rentals are available, but not included.
The Bolt (NE Rando Race Series)
Mount Greylock/Greylock Glen
Rando ski racing (short for randonnée) hearkens back to skiing’s early days, when skiers challenged the mountain both up and down, without the help of chairlifts or tow ropes. “The Bolt,” is one of eight events in the NE Rando Race Series, which includes “The Beast” at Berkshire East in Charlemont and “The Sun” at Bromley Mountain in Peru, Vt. Participants will meet at the Greylock Glen gazebo that morning and ascend the mountain with the aid of “skins” and ski back down. Trails included in this backcountry ski race include parts of the Thunderbolt and Bellows Pipe.