Long before our parents had us dressing up like Power Rangers or our own renditions of Michael Jackson’s “Thriller” look, cultures across Africa, the Caribbean and the Americas had their own ways of marking this time of year. While we were racing door to door in our neighborhoods trying to see how much candy we could fit in a pillowcase, families in those cultures were tending to a connection between the living and the dead. Families built altars, cooked their ancestors’ favorite dishes and told stories meant to keep certain spirits at a safe distance. Many of those traditions are still going strong, and some of the best places to experience them are a short flight away.
If you’re looking to do something a bit different this year, you’ll have a full weekend to mix the fun with the history. With Halloween on a Saturday this year, that could mean a costume parade on Friday night, a cemetery tour on Saturday afternoon and a candlelit vigil on Sunday (all while still dressing up and hitting a party or two in between). It could also mean skipping the scares altogether and sticking to museums, historic homes and a few good meals. A few of these destinations are an easy flight (or drive) from most U.S. cities, and others are worth using a couple of vacation days, because who doesn’t love using their free will for a bit of whimsy?
Here are seven cities worth booking for the holiday, ranked by vibe.
Mexico City, MX
The vibe: A party with the ancestors, and everyone’s invited.
For most people, when they think about Halloween they instantly think about Día de Muertos. And when you think about Día de Muertos, you probably almost instantly think about Mexico City. Beyond the food (because the food in Mexico City is really, really good), there’s plenty of things to do. The whole city gets in on the Día de Muertos party, so plan to spend as much time wandering as you do at the big events. In Coyoacán, for example, homes and plazas set up altars covered in photos, candles and the favorite snacks of loved ones who’ve passed. As you go through, you’ll want to grab a tamal and a cup of champurrado from a street cart and keep walking. The Grand Parade takes over Paseo de la Reforma at 2 p.m. on Saturday, October 31, with giant skeleton puppets, dancers and floats covered in marigolds. After dark, ride a trajinera through Xochimilco to watch performers bring the legend of La Llorona to life on the canals. Stay at the St. Regis Mexico City on Reforma, and when the parade ends you’ll be close enough to walk back and change for dinner.
New Orleans, LA
The vibe: Part party and part history lesson.
New Orleans will gladly accept any excuse to dress up, so Halloween here is pretty much the warm-up for Mardi Gras. By day, the Krewe of Boo parade rolls through the French Quarter with floats and throws, and by Halloween night, Frenchmen Street is packed with brass bands and people in costumes that put your store-bought one to shame. Larry Morrow, the city’s unofficial party mayor, has Spicy Mango right on that same strip, and his lineup also includes Morrow’s, Sun Chong and the Decatur Street nightclub HIDE/SEEK. Licensed guides lead morning tours of St. Louis Cemetery No. 1, and many visitors go to see the tomb believed to belong to Voodoo priestess Marie Laveau. To learn how Voodoo took root in the city, set aside an hour for the New Orleans Historic Voodoo Museum on Dumaine Street.
Savannah, GA
The vibe: Anyone who loves a good scare.
Savannah has easily earned its reputation as one of the most haunted cities in America. With Spanish moss hanging over nearly every square, just know that even a short walk after dinner can feel like the opening scene of a horror movie (and you know how we always end up in those). It’s also one of the few places where you can stroll the Historic District with a cocktail in a to-go cup, so your ghost tour can double as a bar crawl. Whether you book a walking tour, a trolley ride or a seat in a converted hearse, expect stops at Colonial Park Cemetery and the Sorrel-Weed House. Chef Mashama Bailey turned an old Greyhound bus station into The Grey, and that restaurant alone is worthy of a trip to Savannah if you’ve never been. First African Baptist Church belongs on your list too, since its congregation ranks among the oldest Black churches in North America.
Chicago, IL
The vibe: A big-city Halloween with a parade and plenty of bars.
A coat over your costume might be necessary in late October (because it is Chicago, after all), but the city still shows up for Halloween. After the Northalsted Halloween Parade wraps up, the crowds pour into Lakeview’s bars and stay well past midnight. Ghost tours around the city lean into Prohibition-era gangster lore and stories from the Great Chicago Fire. Head south to Bronzeville, the neighborhood known as the Black Metropolis during the Great Migration, and walk past landmarks like the Victory Monument and the Ida B. Wells-Barnett House. Chef Erick Williams won a James Beard Award for the Southern cooking at Virtue in nearby Hyde Park, so book a table there before you change into your costume. The Fairmont Chicago Millennium Park makes a smart home base because it’s close to the lakefront and an easy ride to the rest of the city.
San Antonio, TX
The vibe: Family-friendly and full of culture.
Thanks to its deep Mexican American roots, San Antonio offers a real taste of Día de Muertos without a passport. Muertos Fest fills Hemisfair with more than 80 community altars, five stages of live music and dozens of local art vendors. It runs October 23–25 this year, so fly in early and turn your trip into a full week of celebrating. The Menger Hotel next to the Alamo has been collecting stories about unexplained guests since the 1800s, and if you’re a ghost-story fan, you should definitely should stop in for a drink at the bar. The Carver Community Cultural Center on the East Side has hosted Black artists since the 1920s, so see what’s on the calendar while you’re in town. Families tend to love this one because so much of the weekend happens outdoors and plenty of it is free.
Hudson Valley, NY
The vibe: Old-school Halloween like you’ve seen in the movies.
If you grew up watching the Headless Horseman chase Ichabod Crane in cartoons, Sleepy Hollow is the real-life setting for all of it. Every October, more than 7,000 hand-carved jack-o’-lanterns light up Van Cortlandt Manor in nearby Croton-on-Hudson for the Great Jack O’Lantern Blaze. You can also visit Washington Irving’s grave in Sleepy Hollow Cemetery, right next to the old Dutch churchyard that shows up in his story. For generations, an enslaved African community lived and worked at Philipsburg Manor back when it was a busy mill. Its history tours tell their story in a way your textbook probably didn’t. Those tours run Mondays, Wednesdays and Thursdays in October, so plan to arrive by Thursday the 29th. On the weekend, the same grounds host Twilight Village, an after-dark event with storytellers, a roving brass band and a pop-up evening market. Metro-North runs right up the river from New York City, so there’s no need for a rental car.
Nassau, The Bahamas
The vibe: Halloween with your toes in the sand.
Some people want ghosts and haunted houses for Halloween, and some people want a rum punch on the beach (we’ll take the rum punch for 500, Alex). Nassau gives you both, and late October is quiet enough that you can have Cable Beach mostly to yourself in the afternoon. At night, head to Arawak Cay with the locals for cracked conch and conch salad made right in front of you. Save room for a nightcap at Graycliff, because that’s where Nassau earns its spot on a Halloween list. Ever since a pirate captain supposedly built the old mansion in the 1700s, people have been swapping ghost stories about it. If you’ve ever woken up and couldn’t move or speak, Bahamian folklore says the Old Hag was to blame.