These 3 Destinations Go All Out for Halloween

Hudson Valley, New York: Literary Legends and Thousands of Glowing Pumpkins

Few destinations embrace Halloween quite like Sleepy Hollow, the Hudson Valley village immortalized by Washington Irving’s “The Legend of Sleepy Hollow.” Visitors can trace Ichabod Crane’s fateful ride through landmarks tied to the tale, including the Old Dutch Church, the churchyard where his flight from the Headless Horseman ends. Of course, no visit is complete without stopping for photos at the Headless Horseman Bridge and the Headless Horseman Statue.

The 175-year-old Sleepy Hollow Cemetery is another essential stop. Irving is buried here, along with prominent figures such as Andrew Carnegie and William Rockefeller. Evening lantern tours add an eerie twist, illuminating tombstones and elaborate mausoleums by kerosene lanterns.

Nearby, Washington Irving’s Sunnyside offers a glimpse into the author’s life beyond his famous tale. Costumed guides lead visitors through his meticulously restored home, sharing stories about Irving’s career, family, and inspirations.

The region’s most spectacular seasonal attraction is the Great Jack O’Lantern Blaze, which transforms Van Cortlandt Manor into a glowing landscape filled with more than 7,000 hand-carved pumpkins. Visitors can wander through elaborate illuminated displays before stopping at the Headless Horseman’s Hideaway for spooky sips and a possible encounter with the Horseman himself.

Where to Stay

Set against a 62-acre woodland backdrop, Windrose on Hudson makes a peaceful home base, pairing easy access to the region’s Halloween attractions with a quiet riverside setting where travelers can recharge between autumn adventures.

The resort is about 20 minutes from Sleepy Hollow and just a couple of miles from Van Cortlandt Manor, with seasonal packages that bundle Blaze tickets with overnight stays.

New Orleans, Louisiana: Spirited Celebrations in America’s Most Haunted City

Often described as the city’s biggest celebration second only to Mardi Gras, Halloween brings elaborate costumes, spirited parties and plenty of supernatural intrigue to New Orleans. The festivities culminate with Krewe of Boo! (Oct. 24, 2026), a Halloween parade featuring impressive floats and costumed performers winding through the French Quarter while tossing toys, candy, beads and more Halloween-themed throws to the crowd.

Considered by many as America's “most haunted city,” New Orleans also has enough ghost stories to fill an entire trip. Guided walking tours lead visitors through the French Quarter after dark, stopping at historic buildings connected to tales of hauntings and the paranormal. Travelers who would rather explore at their own pace can follow a self-guided tour of haunted landmarks in the Big Easy, ranging from storied bars and bookstores to historic homes.

Several spooky shows and books have also drawn inspiration from NOLA. Fans of “American Horror Story: Coven” will recognize several locations around the city. The Buckner Mansion, for instance, served as the exterior of Miss Robichaux’s Academy, while the infamous LaLaurie Mansion also figured prominently in the series.

Families can trade ghost stories for trick-or-treating and seasonal entertainment during Boo at the Zoo at Audubon Zoo (Oct. 16-18, 2026). Costume hunting can become part of the itinerary, too, with plenty of vintage stores, thrift shops and costume boutiques throughout the city.

Where to Stay

Just three blocks from the French Quarter, The Old No. 77 Hotel & Chandlery provides an appropriately historic home base.

The art-filled hotel occupies an 1854 warehouse that once stored coffee before becoming a chandlery (a nautical shop) selling canvas, rope, tobacco, paper and other supplies for sailing voyages. Guests can also borrow complimentary bikes to explore the city on two wheels.

Santa Cruz and San Jose, California: Mansion Mysteries and Seaside Halloween Fun

California may be known for its sunshine, but it can show off a darker side, too, during spooky season, with Halloween-themed adventures in San Jose and Santa Cruz.

The marquee stop is the Winchester Mystery House, the famously puzzling 160-room mansion built over the course of nearly four decades by Sarah Winchester, widow of firearms heir William Wirt Winchester. Its labyrinth of twisting hallways, staircases that lead to ceilings and doors that open onto walls—or thin air—has inspired generations of ghost stories. According to one legend, Winchester continuously expanded the mansion to confuse the spirits she believed were haunting her. The house has also inspired books and films, including the supernatural thriller “Winchester,” starring Helen Mirren as Sarah Winchester.

Visitors can explore the sprawling estate through guided tours, with add-on experiences that venture into areas such as the attic and basement. During spooky season, the mansion also leans into its eerie reputation with Festival Fright Nights on select evenings. The event fills the estate with haunted attractions inside the historic mansion, live entertainment, photo opportunities, seasonal food and drinks, and a spooky speakeasy.

About 35 miles away, Santa Cruz offers a lighter take on Halloween. On Oct. 31, Halloween at the Boardwalk will pair trick-or-treating and costume contests with the amusement park’s classic rides. On Wednesdays throughout October, Boardwalk Fright Flicks will screen scary movies inside the Boardwalk’s historic Cocoanut Grove ballroom for guests 21 and older.

Where to Stay

Set on 300 wooded acres in the Santa Cruz Mountains, Chaminade Resort & Spa provides a peaceful counterpoint to the weekend’s haunted happenings. The mountaintop resort overlooks Monterey Bay and features three miles of hiking trails winding through redwood and eucalyptus trees, along with heated pools, a spa and scenic outdoor dining. It is within easy reach of the Boardwalk and about 30 miles from the Winchester Mystery House.

Travelers visiting over Halloween can also attend Chaminade’s 21-and-older Vampire Ball, a ticketed event on Oct. 31, featuring a heavy-bites buffet, cash bar, DJ, fortune tellers, fire dancing, costume contests and photo opportunities.

Explore more destinations across the Benchmark Resorts & Hotels portfolio, a collection of distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.