Whether you are after ghostly encounters, haunted history, or family-friendly fall traditions, taking a vacation this Halloween will offer incredible memories of the spooky season. Among the best choices for the Halloween season are Key West, New Orleans, Orlando, and Chicago. Each city offers something unique, whether it is a particular event, vibrant culture, or spooky sites to visit. A Halloween-themed adventure can also be the perfect excuse to escape to warmer weather amid the dropping autumn temperatures. Or, it could be a trip to somewhere you can experience fall foliage amid the changing seasons, depending on what you are looking for. Continue reading to learn more about why these U.S. cities make the best places to travel for Halloween celebrations.
- Key West: Home to Iconic Ghost Tours and Haunted Places
- New Orleans: Attend Halloween Events and Explore the City's Haunted History
- Orlando: Experience a Halloween Party at Walt Disney World
- Chicago: Celebrate Halloween Midwest Style
- Rent a Timeshare for Haunted Happenings in the Best Places to Travel for Halloween
Key West: Home to Iconic Ghost Tours and Haunted Places
Along with the history that Key West is famous for, it is also renowned for being home to many ghosts of the city’s past. Some people even consider it to be one of the most haunted places in the USA. Ghost tours are a very popular activity in Key West year-round, but especially for those looking for haunted attractions during Halloween. The Ghosts & Gravestones tour travels the streets of Key West at night on a trolley called “Trolley of the Doomed.” While on the tour, you will learn about the historical significance of the small town of Key West and its haunted reputation. Keep your eyes peeled; you may even catch a glimpse of some paranormal activity.
In addition to taking a ride on the ghost tour trolley, there are some other spooky spots that you can explore on your own. One of the most popular sites is Audubon House and Gardens. This museum, located on Whitehead Street in the historic district, is said to be haunted by the ghost of Captain Geiger. This captain was the owner of the house and a well-known wrecker. People claim to have seen him wandering through the house and gardens and even standing on the balcony. There are theories that he is guarding the fortune that is believed to be buried on the house’s grounds.
For those who want to experience some ghostly encounters this season, Key West definitely finds itself among the best places to travel for Halloween.
Stay at Hyatt Sunset Harbor in Key West
Looking for the perfect place to stay during Halloween festivities in Key West? Hyatt Sunset Harbor is the perfect place to spend your Halloween vacation. Here, you are not far from the best Halloween experiences, like ghost tours, the famous Duval Street, and more. What’s more, due to the year-round warm temperatures in Key West, October remains a great time to enjoy the resort’s gorgeous pool and beach access. This can enhance your trip by not only offering great Halloween activities but also providing an escape from the dropping temperatures elsewhere. It is also a fantastic home base for your trip, thanks to its spacious rooms, which are equipped with amenities that enhance your experience.
New Orleans: Attend Halloween Events and Explore the City’s Haunted History
Another spooky town that is one of the best places to travel for Halloween is New Orleans. Similar to Key West, this is another excellent destination for a ghost tour. While ghost tours are always available in New Orleans, spooky season is the ideal time to take one. French Quarter Phantoms offers walking tours led by expert guides who explain the legends of ghosts and paranormal activity in the French Quarter, stopping at the town’s landmarks along the way.
For family-friendly activities in New Orleans, you can participate in Ghosts in the Oaks: Monster Mash at City Park. This event will include trick-or-treating, arts & crafts, a pumpkin patch, and hot dog roasting. Keep in mind that the Monster Mash requires an entry ticket. However, if you are looking for something free to attend, check out the Boo Carre Hauloween Haunt in Dutch Alley. The French Market District will be hosting this event. It will feature live music, free children’s activities, trick-or-treating, and more.
Stay at Quarter House in the Heart of New Orleans’ French Quarter
If you are looking to stay somewhere that will place you steps away from the best Halloween festivities that New Orleans has to offer, then Quarter House is the place for you. This resort is ideal for the Halloween season, thanks to its prime location and New Orleans-style decor. While staying here, you can enjoy your fall days exploring the gorgeous city, and Halloween nights taking a ghost tour or attending all of the area’s haunted happenings.
Orlando: Experience a Halloween Party at Walt Disney World
Throughout the fall, Magic Kingdom showcases its Halloween decorations, featuring fall colors, pumpkins, scarecrows, and more. However, if you want to dive into the Halloween spirit beyond just visiting the park during the day, you can attend Mickey’s Not So Scary Halloween Party! This Halloween-themed event takes place on select nights from August to October and features a range of family-friendly activities that everyone is sure to enjoy.
There is trick or treating, shows in front of the castle, fireworks and more! One of the highlights is the Boo to You Parade, which starts with the headless horseman riding down Main Street. Attending the Halloween party is also a great chance to dress up; some people even go all out with elaborate costumes. Many families also love seeing their favorite characters dressed up in Halloween costumes. This event is perfect for those looking for the best places to travel for Halloween, without any scares.
Spend a Frightening Night at Universal Orlando
Mickey’s Not-So-Scary Halloween Party isn’t the only great Halloween offering you will find in Orlando. Universal Studios in Orlando also hosts its famous Halloween Horror Nights. At this event, you will find several different haunted house options that are sure to provide plenty of frights! The haunted house attractions feature everything from recent horror movies to classics, as well as original concepts. In these houses, you will walk through multiple themed rooms where scare actors will pop out to spook visitors. There are also “scare zones” where scare actors create an even more spooky atmosphere. Keep in mind that this particular Halloween event is not recommended for children under 13.
Stay at Westgate Vacation Villas in Orlando
Being just one mile away from Walt Disney World, Westgate Vacation Villas is conveniently located for all things theme park. Whether you want to spend a night at Mickey’s Not So Scary Halloween Party, Halloween Horror Nights, or both, this resort is never too far from the fun. Orlando is another Florida destination where you can enjoy warm weather, perfect for swimming and taking advantage of the resort’s outdoor amenity spaces. This resort’s villa-style accommodations are also perfect for groups or families traveling together.
Chicago: Celebrate Halloween Midwest Style
The Midwest is an ideal place to spend the fall months, with vibrant fall foliage and beautiful weather. If you want a blend of gorgeous fall views, family fun, and spooky sites, then Chicago is the perfect Halloween destination for you. In the surrounding areas of Chicago, you can find family-friendly farms that offer a variety of fun activities. Some of these activities include pumpkin patches, haunted mazes, spooky experiences, or even costume contests. If you want to stay in downtown Chicago, the Upside Down Halloween Parade is an annual favorite. This parade is an all-ages daytime event that is inspired by celebrations like Carnival or Mardi Gras.
Or, if you are looking for something for even more spooky things to do, dare to explore some of Chicago’s notoriously haunted places. There are a couple of famously haunted hotels in Chicago: The Drake Hotel and Congress Plaza Hotel. Both of these places have had visitors report seeing spirits roaming the grounds.
Stay at the Hotel Blake in Chicago
This Bluegreen Resort is a stylish Chicago favorite located in one of downtown Chicago’s most vibrant neighborhoods. While staying at this resort, you will be within walking distance of Millennium Park, Soldier Field, and the Willis Tower. With this fantastic location, you can enjoy the city’s gorgeous fall colors and iconic Halloween celebrations without ever being too far from your home base.
Rent a Timeshare for Haunted Happenings in the Best Places to Travel for Halloween
Want to spend your Halloween exploring one of these haunted cities and learning about their dark histories and ghostly legends? Or celebrate Halloween at themed parties or street fairs? You can enjoy significant savings on your trip by renting a timeshare in Key West, New Orleans, Orlando, or Chicago. Timeshare resorts in these Halloween wonderlands are all great options for spending a Halloween vacation in style and luxury. Learn how to rent a timeshare and get started on planning your spooky season getaway.
