How to Plan Your Most Festive Night Out This Holiday Season

What makes this time of year a time of cheer? Shimmering light displays, mugs of festive drinks, after-dark shopping and nights out with friends, dressed in holiday style.

Rooftop Fun

Up on the rooftop, clink, clink, clink! Toast the season atop a sleek hotel—hygge included. At VASO at the AC Hotel in Dublin, Ohio (near Columbus), nosh on Spanish tapas and holiday cocktails in a cozy igloo. In the Gateway City, warm up with Smoky Hot Chocolate around firepits or under pergolas at The Chalet at Le Meridien St. Louis Clayton. Get your blood pumping at Chicago's Upstairs at The Gwen—groups of up to 10 friends compete on an outdoor curling rink. The 45-minute sessions also include a Curling Cocktail and sweets for each participant. (Game for more? The Emily Hotel, also in Chicago, has four rooftop curling rinks.)

Holiday Food Experiences

Holiday baking is fun. A culinary experience with no dishes to wash is even better. In Ohio, Columbus Food Adventures leads walking tours around the Short North Arts District. The Holiday Cheer Tour, held in December, pairs seasonal adult bevvies with light bites at seven stops. In Wichita, the modern Mark Arts building hosts food and wine classes year-round and pumps up the holiday programming beginning in November. Learn what wine to serve at the holiday table (November 15), take a gluten-free treat-making class (December 2) or master the art of crepes (December 21). Head to the lake for a scrumptious sail on Chicago's Christmas Eve Premier Dinner Cruise. Enjoy a three-course meal while floating past the city skyline. Take in the views from open-airroof decks or dancethe night away with beats from a DJ.

At the Theater

Tap your toes, sing along or shed a happy tear for George Bailey.

Funky Butt Brass Band, December

Come dressed in Christmas pj's or an ugly sweater and dance to funk and soul renditions of the classics at Funky Butt Brass Band shows in St. Louis (the band's hometown); Omaha; and Kansas City, Missouri.

South Dakota Symphony Orchestra, December 9-10

Attend two jovial shows with the SDSO at Washington Pavilion in Sioux Falls. The 'Tis the Season medley includes carols and a sing-along portion.

A Drag Queen Christmas, November-December

Get tickets to the most fabulous touring show of the season. A Drag Queen Christmas stops in multiple Midwest cities, including Detroit; Grand Rapids, Michigan; Dayton, Ohio; and St. Louis.

Chicago A Cappella, December 8, 10, 16-17

Trade silver bells for talented voices harmonizing holiday favorites. Holidays a Cappella features classics like "Joy to the World." The group also has a Hanukkah concert December 7.

Detroit Symphony Orchestra, December

DSO packs December with seasonal shows. Watch your favorite holiday movie with a live symphony score or get tickets to one of the signature Home for the Holidays performances.

It's A Wonderful Life: A Live Radio Play, December 8-10, 14-17, 20-23

Frank Capra's 1940s classic comes to life (and a few angels get their wings) as a radio play at The Saint Paul Hotel in St. Paul for the 17th season.

Light Shows

What can we say? The Midwest is lit. During Garden Glow at the Missouri Botanical Garden in St. Louis, nearly 2 million lights dazzle, and the domed Climatron gleams like a giant igloo. At the Detroit Zoo's Wild Lights, animal sculptures twinkle around every bend. (Adults can go December 7 for Polar Beers.) Wander the grounds of Newfields during Winterlights in Indianapolis for a stunning feast of lights and projections—best paired with an Electric Reindeer brew from Sun King Brewery. Or head to Indy's Monument Circle for a history and holiday lights walking tour with Sampson Levingston of Through2Eyes. Hop aboard a bus for Brews 'N Bulbs with Twin Cities Brewery Tours and admire some of the cities' best light displays between suds stops. Take a walk in the woods at Cincinnati Nature Center, where light displays inspired by flora and fauna line illuminated trails. Music, food trucks and gift vendors add to the mood.

Pop-Up Bars

Cascades of tinsel, Santa mugs, ugly sweaters: Yep, you've walked into a holiday pop-up bar. The biggie is Miracle, a franchise that takes over watering holes in cities nationwide. Here are six others to try.

Salute to Santa, Indianapolis

Sip seasonal cocktails in the bedazzled tasting room at Hotel Tango Distillery, owned by a veteran with a passion for whiskey.

Sippin' Santa at the Skip, Detroit

Launched in 2018 as the tropical companion to Miracle, this downtown pop-up pours tiki specials like the Jingle Bird and the Surf Nut (with rum, apricot brandy and coconut).

8 Crazy Nights, Chicago

Graystone Tavern hosts the city's only Hanukkah bar, serving up Gelt Martinis, Mensch Mules, latkes and brisket sandwiches.

Jingle Bar, Excelsior, Minnesota

The Old Log Theatre transforms a 125-plus-year-old cabin into a holiday haven. Have a drink around the fireplace and you'll feel right at home.

Cocktail Countdown, Sioux Falls, South Dakota

Forget 12 days of Christmas; how about 24 days of cocktails? Downtown staple Carpenter Bar releases a new drink each day leading up to Christmas.

Holiday Hut, Omaha

At the Cottonwood Hotel, Holiday Hut is the Pool Club's December alter ego. Cozy up by the hearth after one of the hotel's seasonal events, like a holiday market or cocktail class.

Santa Bike Rides

Santa doesn't always take a sleigh—sometimes he prefers two wheels. And sometimes he rolls deep. During Santa Cycle Rampage, 1,000-plus people pedal through Milwaukee dressed as St. Nick and his elves (December 2 this year). Organized as a fundraiser for Wisconsin Bike Fed, the ride is so popular that it has inspired a sister event in Madison, Wisconsin (December 9).

Artisan Shopping

Buying gifts doesn't have to be a grind. Gather the pals and hit one of these artisan markets or late-night shopping events.

Christkindlmarket, Chicago

Where Daley Plaza, Wrigleyville, and RiverEdge Park in Aurora

When November 17–December 24 (Daley Plaza and Aurora); November 17–December 31 (Wrigleyville)

What The Midwest's biggest spin on Germany's famous holiday markets, with crowds sipping souvenir mugs of glühwein, snacking on pretzels and wursts, and browsing imported and local wares.

East Village Holiday Promenade, Des Moines

Where East Village

When November 17–December 15 (Fridays)

What During special evening hours, downtown neighborhood boutiques host shoppers with cocktails, snacks, hot chocolate, Santa appearances and family-friendly activities.

Moonlight Madness + Midnight Madness + Kerrytown Kindlefest, Ann Arbor, Michigan

Where State Street District (for Moonlight), Main Street/Downtown (for Midnight), Kerrytown District (for Kindlefest)

When December 1

What A trio of evening events, where stores stay open late in State Street, Main Street/ Downtown and Kerrytown, and drinks flow for strolling shoppers.

Julmarknad Handcraft Market & Festival, Minneapolis

Where American Swedish Institute

When December 1 (preview night), December 2–3 (market)

What A ticketed celebration of the Swedish tradition of slöjd (handcraft), with vendors selling glass, clothing, wood, jewelry, ceramics and textiles.

Suite Treats at Hotels

Looking for a seasonal staycation? At The Peninsula Chicago, couples can book the Merry and Bright Holiday Package, which includes a menorah or Christmas tree in the room, a bottle of champagne or wine upon arrival, and breakfast for two each morning. The hotel also offers a daily holiday tea service, plus Christmas Day brunch. At the Hilton Cleveland Downtown, kids love the Mr. Kringle Suite, which comes decked floor-to-ceiling and includes nightly milk and cookie delivery. Or book the Mrs. Kringle Suite at the Hotel Indigo Cleveland Downtown and get a personal note from Mrs. Kringle. The joyfully decorated room also includes not one, but two sparkling Christmas trees.