Six Bold Destinations for Celebrating Halloween

With pumpkin carvings, costume parties, and haunted attractions already filling up our October calendars, it is clear that celebrating Halloween is more than just trick or treating on October 31. It’s a full season. And it’s not just kids that consider October the best time of year.

So, with the Halloween holiday season upon us, perhaps you were wondering where best to experience it all? Well, don’t get too scared if you don’t know, we are here to help with six bold destinations to visit for celebrating Halloween.

Salem, Massachusetts

The Burying Point Cemetery dates back to 1637 is a destination for celebrating Halloween.
The Burying Point Cemetery dates back to 1637 and is a known resting place for many historical people involved in the Salem Witch Trials.

Salem is home to American literature giant Nathanial Hawthorne and holds a deep sailing history, yet no doubt it remains most famous for the witch hunt and hysteria that gripped the town over three hundred years ago. Beginning in 1692, over two hundred people found themselves accused of practicing witchcraft, with 19 convictions leading to some grim endings. So a visit here means a visit to the Salem Witch Museum, which is dedicated to these trials and tribulations.

Also, with its popularity, the coastal city embraces its past with an entire month of Haunted Happenings. A grand parade kicks off the celebrations in early October, which includes ghost tours, family film nights and a grand finale of fireworks on Halloween night.

Sleepy Hollow, New York

Philipsburg Manor in Sleepy Hollow, New York - destination for celebrating Halloween
Philipsburg Manor in Sleepy Hollow, New York

Like pumpkins? Jack O’ Lanterns? What about the Headless Horseman?

From late September through November, New York State’s historic Hudson Valley embraces one of its most famous haunted tales, and visitors can see the musical, The Legend of Sleepy Hollow, based on Washington Irving’s classic. Plus, you can spend time searching for his grave and more on the local cemetery tour, which is complete with lanterns for evening hours.

There is also Horseman’s Hollow (not for the faint of heart or young children) to frighten and seriously unsettle folks, too. All these towns in this valley keep festival lights for the entire month or longer.

New York City

The annual Village Halloween Parade in New York City best destination for celebrating Halloween
The annual Village Halloween Parade fills Sixth Ave with 60,000 marchers & 2,000,000 spectators celebrating revival.

New York City hosts multiple parades, but one can’t-miss affair is the Halloween Parade through streets of Greenwich Village.  With costumes to fright as well as entertain, the parade offers the opportunity for everyone to experience the uniqueness of New York’s famous village neighborhood. (Note: anyone with a costume can march in it!)

If a parade is not your cup of tea, how about the annual séance to bring back famous magician Harry Houdini. Years after his death on Halloween in 1926, a séance was conducted to set the stage for his greatest magic trick of all time—the return of Harry’s spirit. Today, the same magicians that lead the event also keep Houdini memorabilia on-site at a museum dedicated to Houdini in the Electric City, Scranton, PA.

Savannah, Georgia

Bonaventure Cemetery with hauntingly beautiful memorials in Savannah, Georgia destination for celebrating Halloween
Bonaventure Cemetery with hauntingly beautiful memorials in Savannah, Georgia hosts the city’s oldest cemetery and resting place to historic figures.

Savannah, an originally urban planned utopian colony, keeps its haunted vibe thanks to a walkable layout of squares with dripping Spanish moss, its antebellum architecture, and close proximity to Civil War battlegrounds and cemeteries.  Filled with ghost tales and ghost tours to keep the spirits alive, the city is a perfect setting for a Halloween adventure at any time, not just at midnight in the garden of good or evil.

Savannah offers both adult-themed and family-friendly events for celebrating Halloween that includes charity balls and galas to commemorate the occasion. There is definitely more to learn about Savannah, and with its sweet southern cuisine, it is the perfect place to satisfy one’s Halloween sweet tooth.

Key West, Florida

Fantasy Fest in Key West, Fl celebrating Halloween annually with a street fair and parade.
Annual Fantasy Fest in Key West, Fl features a two-day street fair and a parade to celebrate Halloween.

No need to wait until Halloween to dress up in Key West. The famous Fantasy Fest, celebrating 40 years of fantasy this year with the theme of “in tune, but off-key,” commences on Oct. 18. Originally created for a “dead” time in the tourism season, this late October festival took its roots in Halloween fantasy and has become a bucket list trip for many craving to travel to the island at the end of the road.

The ten-day event now encompasses more than sixty parties, constant costume-filled marches, street fairs, and glamorous balls, as well as the show-stopping Fantasy Fest parade. By the time Halloween arrives, many locals are once again searching for new costumes—well, that is if they even wore one at all at Fantasy Fest.

Oaxaca City, Oaxaca, Mexico

Oaxaca Mexico during Day of the Dead is a destination for celebration Halloween.
Catrina, a traditional Mexican woman sculpture, during Day of the Dead celebration in Mexico.

Halloween is just the beginning in Mexico, where the country celebrates Dia de los Muertos (Day of the Dead) from October 31 through November 2.  In Oaxaca City, families make ofrednas or altars to remember and receive the souls of the departed. Also, many participate in comparsas, the local traditional parades that can be compared to Mardi Gras. During this holiday, the cemetery is not a place to be spooked, but rather a festive place with people leaving offerings, candles, and flowers, and many are found even drinking and eating with the souls of the departed (who are believed to have returned home).

The Disney animated film “Coco” took its inspiration from Oaxaca to be its Santa Cecilia, the land of the living, and if you want to discover more, follow along my Instagram @StayAdventuorus to watch the celebrations unfold from Oaxaca this year.  I’ll be traveling with a small group from Authentic Mexico Travel to experience this holiday on October 28-November 3.

The notion of celebrating Halloween continues to grow and depending on where you are, the celebrations can be vastly different. These six places offer visitors the chance to appreciate the season at its best.

About the Author

Craig Zabransky is an ex-global management consultant for top-tier banks gone rogue. After a year-long travel sabbatical, he decided to leave Wall Street to pursue his passion for travel. With the belief travel is a gateway to positive life change he podcasts, writes, blogs, and photographs his adventures to inspire others to take and make adventure in their life. To date, he has traveled through more than 55 countries, 40 U.S. States, 5 continents, and is still traveling from his home in the Florida Keys. For more of his story visit his site
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