Cellar Dinner Series — Library Wines with Bookcliff: 6 p.m. Monday, Bramble & Hare, 1970 13th St., Boulder. Bramble & Hare and Bookcliff Vineyards will celebrate more than two decades of Bookcliff Meritage wine at Bramble & Hare. This vertical tasting, with a multicourse meal crafted to enhance the wines, is a once-in-a-lifetime event, the culmination of more than 20 years of Bramble & Hare cellaring classic Bookcliff vintages. $87 per person, opentable.com/bramble-and-hare.

Hanukkah on Pearl: 5:30 p.m. Monday, Pearl Street Mall, 1303 Pearl St., Boulder. Open to the entire community, this outdoor, annual event has become a holiday ritual for many local families. Perfect for all ages, there will be a menorah lighting, music, Hanukkah treats and hot chocolate. Free, boulderjcc.org.

Transgender Proud exhibit: 6 p.m. Monday, Dairy Arts Center, 2590 Walnut St., Boulder. Award-winning photojournalist Sal Skog will share stories in words and pictures to celebrate the extraordinary lives of transgender people. These engaging and deeply moving personal stories illuminate not only what it means to be transgender, but what it means to be human. Free, eventbrite.com.

Hanukkah on Ice: 4 p.m. Tuesday, Winter Skate, 824 Front St., Louisville. Skate with family and friends to Hanukkah music, stay for the lighting of the Hanukkah menorah and enjoy delicious sufganiyot (jelly donuts) and hot chocolate. Free, boulderjcc.org.

Son Little at Fox Theatre: 7 p.m. Wednesday, The Fox Theatre, 1135 13th St., Boulder. Trading in the existential dread permeating his previous work for unbridled joy and self-acceptance, Son Little transmutes the chronic pain of self-doubt into a beautiful and freeing opus about overcoming generational trauma in his new album. Son Little performs vocals and guitar with his band of Steve McKie on drums and DeShawn Alexander on keys and bass. $25-$28, z2ent.com.

Christmas with the Canadian Brass: 7:30 p.m. Wednesday, Macky Auditorium, 1595 Pleasant St., Boulder. The world-renowned Canadian Brass is back to help Boulder ring in the holidays with joyful brass music and merriment. With their signature blend of impeccable musicianship, humor and audience engagement, this brass group is sure to spread holiday cheer. $20-$90, 303-492-8008, cupresents.org.

Kimberly Morgan York at The Velvet Elk Lounge: 8 p.m. Wednesday, The Velvet Elk Lounge, 2037 13th St., Boulder. Athens, Georgia’s own Kimberly Morgan York is at it again this year with her new EP release, “Devil Songs and Other Such Nonsense.” The Kentucky-born artist follows up her 2006 and 2021 recordings with a whimsical project birthed by accident in a bandmate’s basement. As always, York brings her Appalachian roots to her country, soulful and honest songs. Free, 303-993-8743.

Creative Holiday Market: 5:30 Thursday, The Studio, 3550 Frontier Ave., Boulder. Come shop art and goods made by local artists and artisans at this annual pop-up shop. This free event will have complimentary hors d’oeuvres, wine, beer and cocktails by Cocktail Caravan. Free, allevents.in.

“Harmonies of the Holidays” vocal performance: 6 p.m. Thursday, Gordon Gamm Theater, 2590 Walnut St., Boulder. Experience the magic of the season with “Harmonies of the Holidays.” The enchanting vocal quartet from Boulder Bach Festival will serenade audience members with folk melodies and cherished holiday songs spanning diverse cultures, traditions and eras. Soprano Alice del Simone, a bilingual musical virtuoso with a background as intriguing as her voice, will accompany the performance. $10-$20; thedairy.org.