Here at Time Out, we love helping you discover the best things to do in your cities, especially during the holiday season. From where to see Christmas lights to the best places to go ice skating and the can’t-miss celebrations in your town, you'll find all the guidance you need to make the most out of this special time of year. Off the clock, our editors are right there with you, taking in a performance of The Nutcracker and raising a glass of soul-warming mulled wine at the local Christmas market, plus a few more of our favorite holiday traditions we won't gatekeep from you.
A festive martini crawl in Manhattan
This is the time of year in NYC for a little extra sparkle and throwback glam. I always make a point to meet up with friends for holiday martinis at what I consider to be my personal holy trinity of Manhattan bars: Bemelmans, King Cole Bar and Grand Central Oyster Bar. (Amen.) The drinks at all three of these classic spots are liquid perfection, but I've found the one at King Cole Bar packs a real punch. You'll probably want to stick to just one or you may find yourself waking up after New Year's.—Will Gleason, North American Content Director
Seeing the Nutcracker by the Boston Ballet
As a little girl, my Dad would take me to see The Nutcracker every year and it was always the highlight of the Christmas season for me. And now, as an adult, the first thing I do when the weather starts to get chilly is book tickets to the Boston Ballet for my husband and me to continue my favorite tradition. Seeing the Boston Ballet’s production of The Nutcracker is a classic Boston holiday activity, one perfect for the whole family; it’s an excuse to dress up and perhaps indulge in a nice meal before or afterward as well—something I recommend to anyone visiting Boston this time of year.—JQ Louise, Time Out Boston Editor
Strolling through Chicago's iconic Christkindlmarket
Braving the frigid, wintry elements is pretty low on the list of things I’ll do willingly. Yet every year, I bundle up and make my way to Christkindlmarket. The German-inspired bazaar, home to a variety of gift vendors as well as food and beverage options, is synonymous with the holiday season in Chicago. No matter the temps, my friends and I will get together to walk around the festive market for ornaments, raclette sandwiches and potato pancakes. And when our faces begin to go numb, the comforting embrace of warm mulled wine—served in charming souvenir mugs—brings us back to life.—Jeffy Mai, Time Out Chicago Editor
Painting the town (Santa-sled) red
One of my best friends' birthdays is a week before Christmas, so as her name is Nathalie, we celebrate "Feliz Natydad" every year. Some years, we ring it in with a glamorous dinner (I'm pushing for the disco room at Dirty French this year). Others have brought blow-out bar crawls where we dress up in holiday regalia and paint entire neighborhoods, from Brickell to Wynwood, Santa-sled red.—Ashley Brozic, Time Out Miami Interim Editor
Walking the Rose Parade route the day before
When I lived on the chilly East Coast, I’d jealously watched the Rose Parade’s sun-kissed, floral start to the year on TV a few times. But I’d barely been living in Pasadena for a day when I was thrown into the part you don’t see on TV: the sidewalk campouts the day before. My wife and I moved into a small studio apartment half a block away from Colorado Boulevard, and the revving engines and vuvuzela blasts were inescapable. So we leaned into it: We strolled a mile or so of the parade route, past setups with inflated mattresses and propane heaters and processions of hot rods and out-of-town football fans. More than a decade later and a few extra blocks removed from the route, the tradition has stuck around; it just wouldn’t be a New Year’s Eve afternoon without a walk through our city on its most joyously messy day.—Michael Juliano, Time Out Los Angeles Editor
Taking in the dazzling holiday lights in NYC
My favorite holiday tradition is walking around New York City to admire all the dazzling lights. I make a point to stop at the major displays, like the Rockefeller Center Christmas Tree, Shine Bright at Hudson Yards, Central Park’s holiday decor, and Lightscape at Brooklyn Botanic Garden. But I also love to marvel at the lesser-known holiday decor. I’ll stop to behold the wreaths hung in the window of a West Village restaurant or the lights covering an Upper East Side townhouse or even the glimpse of a Christmas tree in an apartment lobby. The city truly sparkles during this time of year, and it’s totally free to appreciate and enjoy.—Rossilynne Skena-Culgan, Time Out New York Things To Do Editor
Tucking into a dreamy Chrismukkah brunch in Miami
Christmas Day brunch at Boia De is sort of a newer holiday tradition for me, but one I look forward to nonetheless. My big Cuban family celebrates Noche Buena (Christmas Eve) and my husband is Jewish, so Christmas morning is just for us. The Michelin-starred restaurant’s annual collab brunch with El Bagel is the dream Chrismukkah experience—bagels, caviar, champagne, and jolly servers topping off your wine glass. We even bring our dog with us, and this year, our carb-loving toddler gets to join the family tradition. Everyone will be merry and well-fed. As is true of any meal at Boia De, reservations are tough but worth it—just don’t take my table.—Virginia Gil, Time Out USA Editor
Seeing the magical window displays in Montreal
A holiday tradition that began when my parents took my sister and I to see once we could walk, the unveiling of Ogilvy's Christmas window officially marks the beginning of the season in Montreal. Much like the department store holiday windows in New York and Paris, the magical display would draw huge crowds every year. Created by German toy manufacturer Steiff, the mechanical animals playing in a Bavarian scene is one of the last of its kind. In 2018 the display was donated to McCord Stewart Museum for preservation, where my young children can visit any time of year.—Laura Osborne, Time Out Montreal Editor
Tree trimming and nostalgic tunes to get in the mood
Every year around this time, my husband and I walk to the idyllic little Christmas tree seller nearby (I just learned their evergreens are all organic, so I’ll be extra vigilant about errant squirrels this year), I brood over branch density, symmetry, and try to identify which fir seems to speak to our household (I am not usually like this), we inevitably pick one just a little too big for our apartment, and Tom carries it back and up three flights of stairs. He puts on the old-timey Christmas music before better selections like Elvis and Mariah Carey enter the mix, and I try to replicate the Jerry Thomas Manhattans that the bartender who officiated our wedding used to make at Schiller’s (the rye must be Wild Turkey). Between piney perfume, the familiar refrains and the whiskey zing, it’s a fast and saturated snap into the holiday season.—Amber Sutherland-Namako, Time Out New York Food & Drink Editor
Sippin' a holiday cocktail at Miracle on 9th in NYC
My Christmas kicks off with the most obnoxious holiday tradition. I go to one of those overly festive bars that feel like a fever dream or like an elf threw up its sparkly red and green guts all over the place. It’s Miracle on 9th, a pop-up that occurs every year at Mace NYC, and it’s been the only one I can rely on to get a reservation (tip: do it before Thanksgiving). My best friend and I go after work every year and slam down about $20 each for one drink that has about a dozen ingredients in it. Is it expensive? Yes. Is it over the top? Absolutely. But it corrects my Grinchy tendencies and snaps me into the Christmas spirit. It’s like a corrective action I take every year to get me on track. Once inside, I have no choice but to give in and let that egg nog mellow my soul.—Shaye Weaver, Time Out New York Editor