Oak Park Arts District’s ‘Art & Wine Walk’

Sat., Dec. 16, 3-7 p.m. , Maychruk Real Estate

Oak Park’s Arts District invites you to its inaugural “Art & Wine Walk.”  Immerse yourself in local art, savor fine wines, and enjoy the evening. For $40, participants receive wine tastings, small bites, Arts District discounts, and exclusive merchandise, including a wine glass, tote bag, and a wine bottle from Anfora Wine Merchants. Check-in is located at Maychruk Real Estate. Limited tickets are available for those 21 and above; purchase online.  911 S. Lombard Ave.

Singers from the Lyric Celebrate December

Monday, Dec. 18, 1:15 – 2:30 p.m., The Nineteenth Century Charitable Association

Indulge in a fusion of classical elegance and festive spirit with a performance featuring four Lyric Opera singers. Experience the magic of the holiday season as the grandeur of opera takes center stage. Reservations required: ncca.memberclicks.net. A recording will also be accessible from the website one week later. 178 Forest Ave., Oak Park. 

‘Elf’ Trivia & Ugly Sweater Night

Wednesday, Dec. 20, 7 – 9 p.m., One Lake Brewing

Test your knowledge on Buddy and his friends from the 2003 classic film Elf.  Don’t forget to wear your best ugly Christmas sweater. Be sure to arrive early to secure your team’s spot or make a reservation at linktr.ee/OneLakeBrewing. 1 Lake St., Oak Park.

Home For The Holidays

Saturday, Dec. 16, 10 a.m.-3 p.m., Downtown Oak Park

This street celebration features a free showing of Polar Express at Lake Theatre (9 a.m.), a special cocoa tasting during the Hot Chocolate Walk (12 – 3 p.m.), a visit with Santa Claus (11 a.m.-3 p.m.), plus live music throughout the district (11 a.m.-3 p.m.). Lake St. & Marion St., Oak Park.

The Nightmare Before Christmas: A D&D Game

Thurdsay, Dec. 14, 6:30 – 8:30 p.m., The Actors Garden

In Christmas town, the abominable snowman and the nutcracker might be friends, holiday myths thrive, and the threat of a Halloweentown invasion lingers. In this Dungeons & Dragons (D&D) two-shot, become a wintry hero facing Jack Skellington’s dark forces. 909 S. Lombard Ave., Oak Park.

Jeff Tweedy at Unity Temple

Thursday, Dec. 14, 6:30 – 10:30 p.m., Unity Temple

Harmonica Dunn and Robert’s Westside proudly present Jeff Tweedy at Unity Temple. When securing advance tickets, please note the limit of 2 tickets per order. 875 Lake St., Oak Park.

Secret Santa Christmas Soiree at the Mansion

Friday, Dec. 15, 6 – 11:30 p.m., Pleasant Home

Experience the festive spirit hosted by the Official Illinois Black Chamber, Cook County Black Chamber, and Garfield Park Chambers of Commerce. This holiday celebration promises a night of music, dancing, and gift exchange with an open bar and hors d’oeuvres and know that your ticket purchase supports the Field of Dreams Visionary Center. Tickets are limited. 217 Home Ave., Oak Park.

‘Annie Jr.’

Friday, Dec. 15 to Tues Dec. 19, 7 – 10:20 p.m., Madison Street Theater

Get ready for the heartwarming Tony Award-winning Best Musical to hit the Madison Street Theater stage this December. Annie Jr. tells the endearing tale of little orphan Annie’s search for her long-lost parents. Brimming with optimism, this family-friendly musical is a must-see for the holiday season. View schedule online. Tickets: $15 for adults, $8 for kids 12 and under at ovationacademy.org/shows-tickets. This all-ages cast production runs approximately 80 minutes with one intermission. 1010 Madison St., Oak Park.

Sing-Along Messiah Concert

Sunday, Dec .17, 3 p.m., First United Methodist Church

Join  us for a sing-along Messiah featuring the renowned Apollo Chorus of Chicago.  A free will offering will be collected to help fund Housing Forward’s mission to end homelessness in western Cook County.  Musical scores will be available for purchase.  For more information on this event that promises to uplift your spirit as you engage in this timeless classic, visit www.firstumcoakpark.org/events. 324 N Oak Park Ave., Oak Park.

Yearn for Peace

Saturday, Dec. 16, 7:30 p.m., Sunday, Dec. 17, 3 p.m., Grace Lutheran Church

Join us to hear music for the holidays that conveys our yearning for peace, from traditional carols and anthems to modern compositions by Abbie Betinis and Levente Gyöngyösi. 7300 Division St., River Forest.

Chocolate Peppermint Donuts

Saturday., Dec. 16, 10 a.m. – 11:30 a.m., Schoolhouse Kitchen + Studio

Designed for children 5 to 11. Young chefs get hands-on experience creating their own donut batter and mastering the basics of measuring and mixing. While the donuts bake, the kids craft chocolate frosting and have a blast with sprinkles and crushed candy canes. Each child takes home a box of 6 donuts to share, making it a memorable culinary experience for all. 349 Ashland Ave., River Forest.

Join the discussion on social media!