Spooky Season on the Road: Building Our Family’s Halloween Travel Tradition

Every year, my brother and I make a point of meeting up somewhere new. Last year, our meetup happened to fall right over Halloween. That’s when we decided to start our new tradition of traveling for Halloween, especially now that our son is old enough to really enjoy trick-or-treating!

Since we’re too busy to travel for Halloween this fall, I’ve been looking back at where this new tradition really took off—and brainstorming where we want to head next.

Back in 2025, we decided to take our Halloween getaway down to one of the most atmospheric, historic cities in the country: New Orleans.

This trip was a major milestone because our son was 2 years old—finally at the perfect age for his very first real trick-or-treating experience. Before flying down, I did a deep dive into NOLA’s best neighborhoods so we could find a spot that was festive, memorable, and completely family-friendly.

The Shadows & Spirits of NOLA: History, Voodoo & Vampires

Before you ever step foot on the trick-or-treating route, you can feel it in the air—New Orleans doesn't just celebrate Halloween; the city practically owns it.

NOLA’s spooky reputation isn't just clever marketing—it's built on centuries of dark history, ghost stories, and unique spiritual traditions. Beyond the famous above-ground cemeteries (the "Cities of the Dead"), the city’s heart beats to the rhythm of Louisiana Voodoo. Rooted in West African spiritual traditions brought to Louisiana in the 1700s, Voodoo evolved over centuries alongside Catholicism, championed by legendary figures like Voodoo Queen Marie Laveau.

Exploring the French Quarter in late October feels like walking straight onto a movie set, surrounded by centuries-old Spanish colonial architecture and shops that cater strictly to the supernatural:

• Voodoo Authentica & Marie Laveau’s House of Voodoo: Tucked into the French Quarter, spots like Voodoo Authentica (on Dumaine St) and Marie Laveau’s House of Voodoo (on Bourbon St) offer a look into real spiritual traditions. You'll find handmade gris-gris bags, potion oils, altar statues, and traditional Voodoo dolls crafted by local practitioners.
• Boutique du Vampyre: Known as one of the first vampire-themed boutiques in the world, this cozy, dark shop on St. Ann Street caters to "vampires and mortals alike." From gothic jewelry and custom fangs to vampire teas, candle charms, and hidden speakeasy clues, it’s a must-visit for anyone who loves dark folklore (or Anne Rice novels).
• Haunted History & Nighttime Energy: As October days wind down, the city lights up with ghost tours, tarot readers set up in Jackson Square, and spooky window displays that set the ultimate mood for a Halloween getaway.

It’s that incredible, historic backdrop that made bringing our family down for Halloween feel so magical before we even put on our costumes!

A Permanent Souvenir: Downtown Tattoos & The Story Behind My NOLA Ink

No major trip feels complete without something to remember it by, but for this getaway, I wanted a permanent souvenir. On October 30th, I went to Downtown Tattoos right in the heart of the city to get a piece custom-designed to capture the trip, our family, and the spirit of New Orleans.

I had a specific concept in mind that tied together the NOLA voodoo vibe with our family:

• The Devil Voodoo Doll & Creepy Tree: A nod to my son’s little devil costume, the spooky local atmosphere, and Louisiana Voodoo history.
• The Paper Airplane: An element with a dual meaning—it symbolizes our family travel tradition while serving as a subtle nod to aviation history (inspired by my son Maverick's name and my grandfather’s history as a WWII fighter pilot).
• The Open Book with Cancer Zodiac Symbol: A tribute to my wife's love of books and our son's star sign (Cancer).

My Experience & Honest Review

I ended up loving the final artwork, but the booking process had a couple of drawbacks:

• No Advance Design Preview: Even though I booked the session months in advance, the shop didn't work with me on the draft beforehand. I had no idea what the final design would look like until I actually showed up at the studio for my appointment.
• Ran Out of Time for Color: I originally planned to get the tattoo fully colored, but due to time constraints during the session, we were only able to complete the linework and shading.

Even with those minor hiccups, it remains one of my favorite pieces—a spooky, meaningful reminder of our son's first trick-or-treating trip and the start of our Halloween travel tradition!

Halloween Morning: Beignets, History & Jackson Square

We kicked off Halloween morning the only right way in New Orleans: with a stop at Café Du Monde. After our very first trip to NOLA years ago, this quickly became our single favorite spot in the whole city, and returning on Halloween made it feel extra special.

The History Behind Café Du Monde

Established back in 1862 in the heart of the French Market, Café Du Monde is a true New Orleans institution. Opening right during the American Civil War, it has served its simple, world-famous menu under the iconic green-and-white striped awning for over 160 years:

• Dark Roast Chicory Coffee: Introduced during the Civil War when coffee beans were scarce, mixing ground roasted chicory root with coffee created a rich, chocolatey flavor that became a signature New Orleans staple.
• Warm French Beignets: These pillowy, square-shaped French doughnuts are fried to order and buried under an absurd mountain of powdered sugar.
• Open 24/7 Tradition: Operating around the clock for generations (only closing on Christmas Day and during major hurricanes), it’s the ultimate gathering place whether you're starting your morning or wrapping up a late night in the French Quarter.

Soaking in the Vibe at Jackson Square

Sitting under the open-air pavilion with hot cafe au lait and powdered sugar everywhere, we took in the morning scenery across from Jackson Square.

Framed by the historic St. Louis Cathedral and the bronze statue of Andrew Jackson, the square comes alive on Halloween morning in a way no other city can match. Local street artists line the iron fences with eerie portraits, brass bands set up on the flagstone walkways, and fortune tellers lay out their tarot cards on folding tables. Watching people stroll by in early costumes while soaking in the autumn breeze made for the absolute perfect, relaxed start to our son's first official Halloween day.

Suiting Up & Mapping the Route: Priests, Nuns & Little Devils

By late afternoon, it was time to head back to change and get ready for the main event. Getting in costume on vacation always brings a different kind of energy to the trip, and luckily, our 2-year-old didn't mind being in costume at all—horns and pitchfork included.

We suited up in our themed attire: my wife and I as a priest and nun, while our son completed the trio as a little devil.

Mapping Out the Uptown Game Plan

While New Orleans has plenty of wild nightlife down on Bourbon Street, trick-or-treating with a 2-year-old required a completely different strategy. We needed an area that was walkable, safe, festive, and easy to navigate with a stroller.

Our plan centered on the Uptown / Garden District area:

1. The St. Charles Avenue Anchor: We decided to start right at the corner of St. Charles Avenue and State Street. St. Charles is wide, well-lit, and lined with iconic historic mansions and towering live oak trees draped in Spanish moss—the ultimate Louisiana backdrop.
2. The Skeleton House Landmark: Starting at 6000 St. Charles Avenue allowed us to hit the legendary Skeleton House right off the bat while our son had peak energy.
3. The Side Street Loop: From there, the plan was to loop down into the quiet residential side streets (like State Street, Rosa Park, and Palmer Avenue), where local families set up full-scale candy stops on their historic porches.

Bucket in hand, we set off heading Uptown, ready for his first official Halloween night!

On the Street: Finding the Perfect Spot & Walking to the Skeleton House

When you're in an unfamiliar city on Halloween night, finding the right neighborhood can feel like a gamble until you actually arrive. We managed to pull in and find parking near the end of a residential street, just a few blocks from the Skeleton House.

As soon as we stepped out of the car, we knew we had nailed it. There were literally hundreds of kids roaming the sidewalks, parents walking together, and houses completely done up in lights, spiderwebs, and jack-o'-lanterns. The energy in the neighborhood was electric, making it instantly clear we had picked the absolute best spot for our son's first real trick-or-treating experience.

Our strategy was simple:

1. The Walk Up: Head down our street toward St. Charles Avenue, trick-or-treating along the way as we made our way straight to the Skeleton House.
2. The Grand Landmark: Spend time admiring the legendary 70+ skeleton display at 6000 St. Charles Ave.
3. The Loop Back: Cross over to the opposite side of the street and make a big, continuous loop back to where we parked.

Walking down those oak-lined sidewalks in our priest, nun, and little devil costumes—surrounded by local families, historic mansions, and mountains of candy—was easily the highlight of the entire trip.

Learning to Trick-or-Treat at the Famous Skeleton House

Watching our 2-year-old figure out the ritual of trick-or-treating in real time was pure magic. At first, he just took in all the sights, costumes, and friendly neighbors, but within a few houses, he had the whole routine down—holding out his bag, saying "trick or treat," and beaming every time another piece of candy dropped in. By the time we made our way to the corner of St. Charles Avenue and State Street, his bag already had a respectable amount of weight to it.

That’s when we arrived at the grand finale of our loop: The Skeleton House (6000 St. Charles Ave).

The Story Behind a New Orleans Halloween Classic

Owned by the Berger family, this stunning 1896 Victorian mansion turns into the city's most famous Halloween landmark every October. What started as a modest display years ago has transformed into a massive community tradition featuring more than 70 life-sized skeletons arranged across the front lawn, wrapped around the porch pillars, and hanging high in the oak trees.

What makes the house so special isn't gore or cheap jumpscares—it's pure creativity and sharp NOLA humor. Every single skeleton is arranged into a clever, pun-filled pop culture reference:

• Music & Legends: Figures like "Marrow-Lyn Monroe," "Pelvis Presley," and "Bone Jovi."
• Local NOLA Flavor: Skeletons playing brass instruments, drinking local beer, or wearing Mardi Gras beads.
• Kid-Friendly Magic: Because the theme leans heavily into lighthearted humor rather than scary monsters, it creates an inviting, festival-like atmosphere where hundreds of families gather on the sidewalk just to read all the signs and laugh together.

Standing in front of that glowing mansion in our priest, nun, and little devil costumes—with our son holding a bag full of candy and marveling at all the skeletons—really solidified why we chose New Orleans to launch our family's Halloween travel tradition.

Late Night in the French Quarter: Voodoo Shops & Absinthe

Once the trick-or-treat bags were full, we decided we weren't quite ready to take off our costumes just yet. We headed down to the French Quarter to soak in the late-night Halloween energy before calling it a night.

The entire Quarter was vibrant and packed wall-to-wall with people. The costume creativity was incredible—every street turned into an impromptu parade of wild, theatrical outfits. Walking through the crowd as a priest, nun, and little devil felt like we were right in the middle of the party.

We strolled through a few local Voodoo shops and dropped back into the Boutique du Vampyre, which hit completely differently at night under the warm glow of street lanterns.

*gifts bought from Boutique Du Vampyre*

A Toast at the Old Absinthe House

To cap off the night, my brother and I slipped into a piece of living New Orleans history: The Old Absinthe House at the corner of Bourbon and Bienville streets.

• Centuries of History: Operating since the early 1800s, this historic building has served drinks to legendary figures like Mark Twain, Oscar Wilde, Franklin D. Roosevelt, and according to local lore, pirate Jean Lafitte and General Andrew Jackson.
• The Atmosphere: Inside, the copper-topped bar, vintage marble fountains, and walls covered in business cards left by decades of travelers give it an unmistakable old-world charm.

My brother and I ended the night by doing a shot of absinthe right at the historic bar—a fittingly bold, traditional NOLA finish to an unforgettable Halloween night.

The Ones That Got Away: NOLA Spooky Spots We Missed

As much as we packed into our time in New Orleans, a city with this much history and dark folklore means you can’t see it all in one trip. With a 2-year-old in tow and a tight schedule, there were a few iconic spooky experiences we had to leave on our wishlist for next time:

• The Cemetery Tours: New Orleans’ famous "Cities of the Dead"—like St. Louis Cemetery No. 1 (the final resting place of Voodoo Queen Marie Laveau)—require licensed guided tours to enter. Between timing logistics and navigating historic cobblestones with a stroller, we had to skip them this round.
• Nighttime Haunted Ghost Tours: NOLA is legendary for its nighttime walking tours covering French Quarter murders, vampiric lore, and famous haunted haunts like the Lalaurie Mansion. While late-night ghost hunting doesn't quite align with a toddler's bedtime, it's high on our list for when our son gets a bit older.
• The Museum of Death: Located right on Royal Street, this museum covers true crime, macabre artifacts, and dark history. Because of its graphic nature and age restrictions, it’s strictly an adults-only spot, so we had to pass on it for this family-focused getaway.

Leaving a few stones unturned just gives us the perfect excuse to plan a return trip to New Orleans down the road!

November 1st: Into the Wilds of Barataria Swamp

On November 1st, we shifted gears from spooky city streets to Louisiana’s raw backcountry by heading out to Barataria for a guided swamp tour. Just a short drive south of New Orleans, the area is crisscrossed by a network of straight, man-made logging canals dug back in the late 1800s and early 1900s to haul out massive cypress timber—an industrial history that completely reshaped the natural bayou landscape into the waterways you travel today.

Since late autumn was setting in, the cooler November weather meant the wildlife was starting to slow down for the season. Alligators are cold-blooded and rely on the sun to regulate their body temperature, so as temperatures drop, they get sluggish and spend less time active in the open water. Even with the chilly air, we still managed to spot a few wild gators gliding through the dark water or basking on log banks along the canal edges.

The Standout Moments

Our guide made the trip unforgettable with two huge highlights:

• Holding a Baby Gator: At one point during the ride, the guide brought out a small, hatchling alligator and passed it around so everyone on board had a chance to hold it. Getting up close with those tiny, armor-like scales was an absolute thrill for the whole family.
• Kissing a Full-Grown Alligator: The absolute climax of the tour came when our guide managed to coax a massive, full-sized wild alligator right up to the side of the boat—and proceeded to give it a quick kiss right on the snout! It was equal parts intense and hilarious, showcase-level swamp entertainment that completely stole the show.

It was the perfect, grounding contrast to the neon lights and crowds of the French Quarter, giving us a true taste of Louisiana's iconic backcountry before wrapping up the trip.

Dreaming Up the Next Trip: Our Future Halloween Bucket List

While New Orleans set the bar sky-high, planning our next big autumn getaway is already half the fun. Here are the top four destinations on our bucket list for future Halloween travel traditions:

1. Ireland: The Birthplace of Samhain

Our absolute top dream destination is Ireland. Halloween traces its roots back over 2,000 years to the ancient Celtic festival of Samhain (SOW-in), celebrated on November 1st to mark the end of the harvest and the onset of winter.

Celts believed the boundary between the living and the dead blurred on October 31st. To ward off wandering spirits, they lit massive bonfires and wore disguises made of animal skins—the very origin of Halloween costumes. Instead of pumpkins, they carved scary faces into turnips and rutabagas to carry embers home from the sacred fires.

Trick-or-treating was known as "guising" or "mumming," where kids performed songs, jokes, or dances in exchange for soul cakes or fruit. Visiting Derry Halloween or spiritual sites like the Hill of Ward during October would be the ultimate trip back to where Halloween was founded.

2. Salem, Massachusetts: The Witch City

We’ve been to Salem quite a few times, but never over Halloween! Experiencing the town during its month-long Haunted Happenings festival turns the entire city into an open-air spectacle.

Beyond the heavy history of the 1692 Witch Trials, Salem during Halloween brings street performers, fortune tellers, and massive costumed crowds along Essex Street. Trick-or-treating through historic districts like McIntire—surrounded by 18th-century architecture, candlelight tours, and pumpkin displays—would be incredible to experience firsthand.

3. Sleepy Hollow, New York: The Legend of the Headless Horseman

Set along the Hudson River, Sleepy Hollow leans fully into Washington Irving's classic 1820 ghost story, The Legend of Sleepy Hollow.

The area is famous for The Great Jack O'Lantern Blaze at Van Cortlandt Manor, featuring over 7,000 hand-carved, illuminated pumpkins. Between lantern tours of Sleepy Hollow Cemetery (where Irving is buried) and dramatic performances of the Headless Horseman at historic manors, it offers a classic, quintessential East Coast autumn atmosphere.

4. Savannah, Georgia: Southern Gothic Haunts

Widely considered one of the most haunted cities in America, Savannah's spooky vibe stems from centuries of history built on top of battlefields, historic plague sites, and native burial grounds.

Draped in heavy Spanish moss, the city's cobblestone squares, antebellum mansions, and haunting spots like Bonaventure Cemetery and the Sorrel-Weed House give it an unmistakable, eerie Southern Gothic charm that would feel right at home for a spooky October getaway.

Looking Ahead: The Next Spooky Destination

Looking back on our time in New Orleans—from holding a baby gator in Barataria to watching our 2-year-old learn to trick-or-treat under the glowing trees of St. Charles Avenue—it’s clear that taking Halloween on the road was one of the best family decisions we’ve ever made.

Even though we’re staying local this fall, planning our next big autumn getaway is already half the fun. Whether we end up sitting around a bonfire in the misty countryside of Ireland, walking the historic brick streets of Salem, tracking the Headless Horseman through Sleepy Hollow, or exploring the Spanish moss and ghost stories of Savannah, I can’t wait to see where our son carries his trick-or-treat bucket next.

Traveling together as a family is great, but taking those traditions on the road over spooky season makes them truly unforgettable. Here’s to the next Halloween adventure!