Everything You Must Do in Cleveland This Winter

You don’t need us to warn you about the colder months in CLE. This isn’t your first winter in The Land. (Or maybe it is. In which case, sorry! And dress in layers!) You know the winter months bring more than just lake effect snow to the area. The season also includes a Santa’s bag worth of cool concerts, live comedy, and a hearty assemblage of food and drink events that will help you not just endure, but almost embrace, the chill over Cleveland. From Christmas Ale to Conway’s Irish Ale, we have your season covered. Here’s everything you must do in Cleveland this winter (and here's everything you should do in Cleveland no matter the time of year).

Through December 22
Cleveland Play House
With The New York Post describing it as “the funniest show about depression,” Every Brilliant Thing is a one-person tour de force from the lauded Cleveland Play House about the things that make life worth living. The role is double cast, so audiences will see either Tarah Flannagan or Alex Brightwell as the solo performer.
Cost: $20-$95

Society Lounge
Society Lounge

Through December 31
Society Lounge
Downtown cocktail standby Society Lounge is getting holidazzled for a charitable cause as part of the worldwide Miracle pop-up bar network. (Georgetown in Lakewood is also turning into The Christmas Corner Bar, so you have your pick of festive seasonal imbibing ‘till New Year’s.)
Cost: No cover (drinks hover around $10-$15)

December 20-22
Hilarities at Pickwick & Frolic
If you enjoy the former Insomniac host’s R-rated material, come see comedy’s favorite grouch Dave Attell hit up Cleveland for five shows just in time for the holidays.
Cost: $25-$35

December 29
House of Blues
The legendary metal monsters from Richmond, Virginia, win the prize for best tour name in recent memory. Witness Gwar’s notoriously fun gross-out stage antics at the Cleveland stop of their current Use Your Collusion US Tour. 
Cost: $25 

December 31
The Side Quest
Sure, you could go to yet another Roaring ‘20s party for NYE this year. Or you could go to a The Shining-themed celebration at Northeast Ohio’s greatest nerd bar. Heeeeere’s your New Year’s! (Too much? Okay.)
Cost: No cover!

January 3
House of Blues
Break your “sober January” resolve early this year with the Holiday Hangover bash at House of Blues. Fun cover bands, Krampuses, and “naughty elves” will help ease you out of your slothy New Year’s recovery mode.
Cost: $13

Uncorked Wine Festivals
Uncorked Wine Festivals

January 11
Great Lakes Science Center
At Uncorked: Cleveland Wine Festival, you can try 100 different varieties of wine and champagne amidst the child-like wonder of the Great Lakes Science Center. The fact that it’s an event raising money for The Adoption Network is a cool added bonus.
Cost: $50-$65

January 22
Will Platform’s big beer buyout affect the quality of their beer? One way to find out is to head to Phunkenship, their new sour-focused facility in Clark-Fulton, for this fundraiser for February’s Brite Winter Fest. Food and a take-home four-pack included!
Cost: $28-$55

January 23-25
Hilarities at Pickwick & Frolic
Best known as the host of Netflix’s epic fail baking show Nailed It!, Nicole Byer is a charming and hilarious writer, actor, and comedian in her own right. Come see her take the stage at Hilarities for a three-night winter engagement.
Cost: $30-$35

January 24
House of Blues
We know Snoop must be entering the later stages of his rapping career. You don’t name your tour I Wanna Thank Me unless you’ve been around the hip-hop block a few times. Maybe Martha Stewart will be there, too? 
Cost: $143 and up

Cleveland Beerfest
Cleveland Beerfest

January 24-25
Huntington Convention Center of Cleveland
Stock up on Bloody Mary mix. Set aside some Advil. Hydrate. These are a few of the things you can do to prepare for the morning after Cleveland Winter Beer Fest, where hundreds of beers will be on tap. So don’t hold back.
Cost: $45-$90

January 25
Asia Plaza
Ring in the Year of the Rat right in AsiaTown’s legendary Li Wah restaurant. There’ll be a traditional lion dance and first-come, first-served dim sum. Pro tip: get there early for that dim sum, son!
Cost: Free

January 25 - February 23
Cleveland Play House
“Mrs. Peacock was a man?” Take the former drama club geek in your life to the Cleveland Play House stage adaptation of Clue, the 1985 cult classic film/board game. You’ll both have fun, even if you have to ask said drama club geek to stop quoting half the lines from their seat. 
Cost: $20-$95

January 28 
Cleveland Museum of Art
Described as a “Dylan-style word ninja” by Rolling Stone, Aussie rocker Courtney Barnett brings her indie cred to an unexpected venue: the Gartner Auditorium at the Cleveland Museum of Art. We’ll go see her anywhere!
Cost: $30-$35

February 1
The Agora 
Calexico and Iron & Wine recently reunited for the collaborative album, Years to Burn. And on their tour of the same name, you’ll have the chance to see both indie lifer acts do some serious subdued emoting on stage.
Cost: $33-$58

February 4-23
Playhouse Square
Though the 1997 movie Anastasia has its fans, writers Lynn Ahrens and Stephen Flaherty have updated their musical for the stage by cutting the goofier kid elements (sorry, Bartok fans) and adding 16 new songs. Let’s see how this turns out! 
Cost: $10-$120

February 7
MGM Northfield Park
Watch as the man best known for shouting at Jackie Chan gears up for a comeback with his new Netflix special and this tour. Do you under-staaand the words that are coming out of Chris Tucker’s mouth? We’ll bet you will. 
Cost: $65-$240

Donut Fest
Donut Fest

February 8
Red Space
Nothing like a little cruller action to keep Clevelanders a healthy distance from their mid-winter blues. A donut? The thing may as well be a life preserver. Grab hold as Donut Fest Cleveland brings together local coffee and donut vendors for a sugary wonder of an evening.
Cost: TBD

February 14
Wolstein Center
This Valentine’s Day, you can go out for an overpriced special at a too-crowded restaurant. Or you and your special someone can get your laugh on at the Comedy Laugh Fest with headliners Cedric the Entertainer and D.L. Hughley. The choice is yours.
Cost: $42-$102

February 16
The Madison
Winter in The Land can be tough. You need some calories to make it through. That’s where the first-ever Cleveland Dessert Festival comes in. A mere $15 gets you 20-plus dessert samples courtesy of treat makers from all over the area. 
Cost: $15

February 18
The Agora
Settle in for a night of uncomfortable stoner comedy with Tim Heidecker and Eric Wareheim, the infamous duo who brought you Dr. Steve Brule and a host of other weird Adult Swim memes.
Cost: $45-$122

February 21
Slovenian National Home
With Dyngus Day firmly established as a Cleveland staple, the folks of Cleveland Kurentovanje are hoping to bring another Eastern European holiday to the masses. This one features giant, fluffy monsters and takes place at one of the city’s most underrated party venues. So give it a shot!
Cost: TBD

Brite Winter
Brite Winter

February 22
Flats West Bank
Sometimes, you’ve got to lean into winter to really enjoy it. That’s the logic of Brite Winter, the outdoor music and arts festival now in its tenth year. Come for the free music, stay for the beers and camaraderie.
Cost: Free! (But not the food or drinks, obvi.)

February 29
MGM Northfield Park
Tracy Morgan lives! The man with the most unfailingly funny delivery in all of comedy (seriously, I would crack up at this guy reading a phone book) brings his No Disrespect tour to the recently renamed MGM Northfield Park. Be there.
Cost: $38-$289

February 29
Playhouse Square
Ripped jeans and flannel. Parachute pants. Your best Ziggy Stardust getup. All of the above are appropriate fashion options under the theme of the 29th annual Jump Back Ball: From Jukebox to Boombox. Dress in the music fashion of your favorite decade and support fundraising efforts for our treasured theater district!
Cost: $75-$200

March 5
Playhouse Square
Iliza Shlesinger does not stop working. Ever. After releasing her fifth Netflix comedy special in almost as many years, the Last Comic Standing winner is taking her Forever Tour to Cleveland. Respect your Elder Millennial! 
Cost: $35-$65

March 6
Wolstein Center
Veteran funnyman Jim Gaffigan has been taking on some serious film roles lately, but his current The Pale Tourist tour offers proof that he can keep the clean-but-still-belly-deep laughs coming.
Cost: $36-$77

March 13
The Agora
We haven’t heard a new album from Three 6 Mafia since 2008, but surviving members of the much-loved hip-hop group are gifting us with a reunion tour. March just got a little easier.
Cost: $69-$125

March 17
Starts & ends on West 6th Street
We’ve all patronized Cleveland’s St. Patrick’s Day Parade but last year, a new tradition started: a Guinness World Records-breaking 5K run featuring more than 2,000 kilted Clevelanders. Let’s see if we can top it this year.
Cost: $40

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Daniel Wessler Riordan is a Thrillist contributor.