Best Spooky Halloween Trips

The frights and delights of All Hallow’s Eve come alive in these five cities

Some people love autumn for the brisk weather, cozy clothing, and the quaint villages where fall foliage is in dramatic display.

Then there are spooky autumn people. The paranormal investigators. The graveyard tourists. The people who can’t wait to get scared by something going bump in the night.

We think touring a spooky town is the perfect excuse for a fall getaway. We recommend these five destinations — charming on their own, but with an extra layer of haunted fun after dark.

Global Air Charters will make your travel to these locations anything but frightening. Our comfortable Gulfstream airframes will help you arrive refreshed and ready to brave a haunted trek through a corn maze. Contact our flight coordinators to book your charter today.

Salem, MA

Perhaps no town in the country is more linked with Halloween than Salem, Massachusetts. The city leans into its bewitched history with one of the longest Halloween festivals in the nation. Haunted Happenings runs throughout October, with ghost tours, haunted houses, and costume parties galore.

You’ll find several spooky events in Salem leading up to Halloween. The Salem Witch Museum has extended hours through October. The House of the Seven Gables hosts nightly performances from literature’s creepiest tales.

Arrival: Boston Logan International Airport (KBOS), about 30 minutes from Salem.

Savannah, GA

Savannah often battles with New Orleans for the title of most haunted city in the U.S. Here you’ll find plenty of ghost tours and cemetery walks. Stops include paranormal hotspots in the town’s most historic districts, like The Marshall House and 432 Abercorn Street.

For more spooky fun, you can creep through the crypts at Bonaventure Cemetery. Or, simply watch the full moon filter through the Spanish moss in one of Savannah’s historic squares. Don’t leave town without eating at The Grey, chef Mashama Bailey’s soulful homage to Port City Southern food.

Arrival: Savannah/Hilton Head International Airport (KSAV)

Anoka, MN

Though lesser-known than the other cities on our list, Anoka celebrates the season like no town in the Midwest. In fact, they’ve christened themselves The Halloween Capital of the World.

A few miles upstream from Minneapolis on the Mississippi River, Anoka goes all out and hosts citywide Halloween events all October long. There are plenty of family-friendly events here, including costume contests, family art days, medallion hunts, and parades.

While you’re in the Twin Cities, get a reservation at Vinai or Oro By Nixta. These two eateries on the same corner of Northeast Minneapolis both made the New York Times’ 50 Best Restaurants of 2024 list.

Arrival: Minneapolis-St. Paul International Airport (KMSP), about 30 minutes from Anoka.

Sleepy Hollow, NY

Made famous by the author Washington Irving, Sleepy Hollow is a quiet village 30 miles north of Manhattan. Since “The Legend of Sleepy Hollow,” the town has embraced its place in spooky American lore and now hosts a month-long Halloween festival.

The Great Jack O’Lantern Blaze features over 7,000 hand-carved pumpkins afire with synchronized lighting and an original soundtrack. There are also haunted hayrides, tours of Sleepy Hollow Cemetery, performances and more.

Arrival: Westchester County Airport (KHPN), about 25 minutes from Sleepy Hollow.

St. Augustine, FL

As the oldest city in the country, St. Augustine is guaranteed to have ghost stories in its legend. Ghost hunters flock to the St. Augustine Lighthouse where paranormal forces are routinely reported. The infamous Castillo de San Marcos has several reported ghosts, from a headless Native chief to a pair of lovers murdered for their affair.

St. Augustine is also home to the Ripley’s Believe It or Not! Museum, which hosts ghost tours and spook museum tours throughout the season.

Arrival: Northeast Florida Regional Airport (KSGJ), just a 10-minute drive to downtown St. Augustine.