Things to Do in Wolfeboro, NH: Winter 2020

Wolfeboro may be best-known as a summer resort, but the same natural wonders that make it a summertime favorite make it a peaceful winter playground as well. The winter months find us skiing (both cross country and downhill), snowshoeing, ice fishing, skating and otherwise embracing the season.

Wolfeboro’s own Abenaki Ski Area was founded in 1936, making it the oldest small ski area in America. Abenaki is a local favorite for its affordability and small town vibe, but if you crave the skiing offered by bigger slopes, then Gunstock is just a half hour drive away.

If you are staying at Pickering House Inn, our staff is always happy to provide suggestions, maps and arrangements to help you make the most of our classic New Hampshire Lakes Region location. You may also want to check out our popular cross country skiing package (you can walk from the Inn to the trails!)

Après ski (or instead of winter sports!), there are plenty of fun things to do! Here are a few of our favorites this season:

Pickering House Chef’s Table Dinners
By reservation most winter Saturdays
5:30 pm – 8:30 pm

Our new Chef’s Table Dinners are a cozy variation on our popular Barn Dinners. Each dinner features a favorite winter menu created by our Executive Chef Jonathan Hudak and Chef Aleks.

Learn more

Winter Warmers Cocktail Class
Tamworth Distilling, Tamworth, NH
Thursday, January 16, 2020
6 pm – 7:30 pm

This workshop includes instructions, ingredients, and of course, sips of three favorite libations to stave off the chill: Hot Toddies, Traditional Gloggs, and Irish Coffees!  Ticket price includes: supplies, instruction and demonstration of three cocktails, Tamworth’s annual Ski New Hampshire poster, and light fare from Tamworth’s Art in the Age Cafe.

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Ice Fest Craft Beer Festival – 19 Mile Bay, Lake Winnipesaukee
Saturday, January 25, 2020
12:00-3:00 pm
21+ only

Both you and the beer will be on ice! This is the third annual Ice Fest sponsored by Wolfeboro’s Beveridge Craft Beer & Soap Company on the ice on frozen 19 Mile Bay (about a 15 minute drive from Pickering House Inn). Wear warm clothing and grips on your shoes are recommended!

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Village Players Classic Movies
51 Glendon Street, Downtown Wolfeboro
Friday and Saturday, the third weekend of the month
7:30 pm

January:  On the Town
February: Shop Around the Corner
Enjoy classic films on the big screen. Popcorn and snacks available. Tickets $5, sold at the door only.

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Cross Country Ski Progressive Dinner
Saturday, February 8, 2020
6:00 pm – 8:00 pm
Abenaki Ski Area, 390 Pine Hill Road, Wolfeboro
The annual progressive XC ski dinner is held on the cross country ski loop trail at Abenaki Ski Area.  Participants can ski, snowshoe or walk the candle-lit 4 kilometer XC loop. There are bonfires along the trail and a multi-course Italian dinner is served at various locations along the way.

Learn more

Sled Dog Championship
February 14-16
Laconia, NH
Teams from all over the world come to nearby Laconia to compete to be the next World Champion! Spectators can enjoy food, entertainment, dog merchandise and, of course, the races!

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Wolfeboro Bay Winter Carnival
Saturday, February 22 through February 29, 2020

Events are held throughout Wolfeboro and include a big air competition, free ice skating, snowshoeing workshop, sleigh rides, animal tracking, primitive fire building, inflatable obstacle course competition, pancake breakfast and ski and snowboard races.

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As part of this special weekend, Pickering House Inn will be offering a special cocktail tasting dinner with Tamworth Distilling on February 22nd (learn more) and the “Fire and Ice Festival” will return to the Wolfeboro Inn just a short stroll from Pickering House. (Get info)