2019 Holiday Activities in Wolfeboro - The Pickering House Inn

Holiday Activities in Wolfeboro: November & December 2019

November and December are special times in Wolfeboro. After the busy summer and fall tourism seasons, the community takes a breath and the pace begins to slow. Simple pleasures such as craft fairs, favorite old movies, parades, tree lighting events, gingerbread workshops, barn dinners, and leisurely holiday shopping in the downtown boutiques recall an earlier era when the holidays weren’t so frantic.

We love to spend November indulging in delicious food, taking a leisurely drive around Lake Winnipesaukee, strolling Wolfeboro’s hiking trails, or spending an afternoon with a good book. As the holiday season gears up, every week offers an array of activities guaranteed to enhance the holiday spirit. Here are a few of our favorite things to do in the weeks ahead:

Barn Dinners: The Barn at Pickering House, Wolfeboro

Dinners at The Barn at Pickering House are a great way to enjoy delicious food while making new friends. The dinners feature a set menu served at large farm tables designed to foster conversation and a sense of community. Our Tasting Dinner and the Holiday Tree Lighting Dinner are already sold out, but as of this writing, seats are still available for our December 14 and New Year’s Eve events! Learn more

Christmas in Wolfeboro

Wolfeboro’s holiday season begins in earnest on November 30th. Start off at the 23rd annual Christmas Craft Fair held at Kingswood High School from 9 am-3:30 pm. Then, catch the annual Christmas parade and holiday tree lighting downtown from 3-5:00 pm. This Wolfeboro tradition is the perfect kick-off to the Christmas season (and to our Tree Lighting Barn Dinner held right after the town tree is lit)! Learn more

Festival of Trees: Wright Museum of World War II, Wolfeboro

The 2019 Festival will be held on the Weekends of December 7, 8 and 14, 15 and Wednesday evening Dec 11th. This popular annual charity benefit features more than 65 trees, uniquely decorated by area businesses and organizations, and displayed on two levels at the Wright museum. In addition to the trees, the exhibit features continuous entertainment and light refreshment. Learn more

Christmas at the Castle, Moultonborough

Castle in the Clouds, a restored estate in nearby Moultonborough, hosts its popular “Christmas at the Castle” event on November 23, 24, 29, 30 and December 1. Tour the mansion and enjoy holiday decor created by businesses and designers to reflect their most nostalgic Christmas memories. Browse the Artisan Fair, have lunch at The Carriage House,and have fun making crafts at this beloved holiday event. [Tickets required]Learn more

The Village Players, Wolfeboro

Catch a live performance of Once Upon a Mattress, a funny musical retelling of the classic fairy tale, The Princess and the Pea, on November 1,2, 3, 8,9 and 10. Not in town those dates? Enjoy a classic movie at the Village Players right in downtown Wolfeboro (walking distance from Pickering House Inn). Mr. Smith Goes to Washington is playing on November 15th and 16th and A Christmas Story airs December 20 and 21st. Learn more

Farmstead Christmas: Remick Country Doctor Museum and Farm, Tamworth

Take a short drive to the nearby village of Tamworth to enjoy a relaxed holiday event at the Remick Country Doctor Museum and Farm on December 7 from 11 am – 3 pm. Learn more

The Nutcracker: Kingswood Art Center, Wolfeboro

Hailed by New Hampshire Magazine in 2018 as one of their top 10 things to do in New Hampshire in December, Northeastern Ballet Theatre’s “The Nutcracker” is the original rendition of this holiday classic ballet. Catch their performance in Wolfeboro on Sunday, December 15 at 2 pm. Learn more

Christmas in the Village, Sandwich

If you missed Wolfeboro’s holiday celebration on November 30, visit the nearby village of Sandwich for its 38th Annual Christmas in the Village Craft Fair and Holiday Celebration on December 7th and 8th. Learn more

Cocktail Workshop: Tamworth Distilling, Tamworth

Looking to celebrate the holidays in a way that is a tad more adult that hot chocolate and cookies? Sign up for Tamworth Distilling’s “Speakeasy Sippers” cocktail workshop in December 19 from 6:00-7:00 pm.  You’ll get a chance to try your hand creating three famous 20’s-era libations, featuring Tamworth scratch-made spirits. Learn more

These are just a few of the many holiday events and activities happening throughout New Hampshire’s Lakes Region in November and December! If you are a guest at Pickering House Inn, please ask our staff to help put together a custom itinerary for you!