Up on the Yonder Holiday Market | November 21, 2026
The Up on the Yonder Holiday Market is back again for 2026. From 11-4pm on November 21st come eat, drink, and shop as you kick off the Holiday season. The first 50 guests to buy a drink also receive a commemorative glass from the event. This year's event includes 15+ local and regional vendors and artists to shop from. So have a drink, enjoy some food to eat, and bring your friends Up Yonder and enjoy this holiday market to start off your holiday shopping season.
North Shore Winery Holiday Market | November 27, 2026
Get into the holiday spirit at the North Shore Winery's annual Holiday Market on Friday, November 27th. Enjoy a warm winter beverage while shopping for holiday decorations, art, gifts, wreaths, maple syrup, wine gift baskets and more from local vendors. The tasting room will be open from 12:30-7pm and the market will be from 12:30-5pm.
Oh Ole Night Parade & Fireworks | November 27, 2026
Kick off the holidays with the Oh Ole Night Parade in downtown Grand Marais the day after Thanksgiving. Enjoy a sweet treat, warm drink, and winter festivities after your day of shopping and see downtown Grand Marais transform into a winter wonderland that could be the main character of any Hallmark Holiday movie. The parade begins at 5:30pm with tree lighting and fireworks to follow.
Hovland Winter Art Market | November 28, 2026
Make your way up Highway 61 to Hovland Town Hall to shop local artists and vendors this holiday season from 10am-4pm on November 28th. This annual event highlights the talents of local artists and craftspeople, featuring a variety of arts, leathergoods, beeswax candles and more!
Holiday Market at Studio 21 | Northwoods Fiber Guild Holiday Sale | December 5, 2026
Join Studio 21 on December 5th from 9am- 2pm during the Grand Marais Holiday Market. The Grand Marais Art Colony will have the Northwoods Fiber Guild holiday sale, free art activities, a pottery sale with local potters, and you can shop at the Art Colony Gallery Store. This is the perfect event to find something for the artsy loved one in your life!
Grand Portage Winter Craft Show | December 5, 2026
The Grand Portage Winter Craft Show is hosted at The Grand Portage Lodge and Casino Event Center. This craft show is Saturday, December 5th from 10- 3 pm. Here you will find handmade crafts, Christmas gifts, vintage items, Christmas decorations, local jewelry and more!
Christmas at the Caboose | December 5, 2026
The Polar Express has nothing on Christmas at the Caboose. Celebrate the start of the Christmas season at the historic 1948 Great Northern Caboose with santa, warm drinks, family photos, a community sing along, and endless holiday cheer on Saturday December 5th from 11:30-2pm. Photographer Bruce Johnson will be offering complimentary family photos on his vintage film camera that guests can take home with them to commemorate the day. All activities are free to the community and have no cost!
North Pole Adventures at Lutsen Mountain | December 21-23, 2026
Hop aboard the gondola and make your trip to the North Pole! From December 21st-23rd enter a winter wonderland that is Lutsen Mountain. Enjoy twinkly lights, visits from Santa, glowy lanterns, holiday crafts, and maybe even some night skiing on Ullr Mountain! So come make memories, and maybe even start to build family traditions of your own at Lutsen Mountain.
