Halloween is more than candy and costumes; it’s a season for stories, history, and experiences that send a chill down your spine. This October, Independent Collection Hotels & Resorts is embracing the season with ghost tours, haunted sites, and themed events that make every stay memorable. From historic streets to coastal legends, here’s where to find your next hauntingly good adventure.

Walk Through the Shadows of America’s Oldest Streets

Few cities capture the Halloween spirit like Boston, where narrow streets and centuries-old cemeteries set a naturally eerie scene. The Whitney Hotel adds its own layer of festivity with the Little Monstah Mash, a daytime celebration on October 26 complete with themed bites, drinks, and family-friendly activities. Later in the week, the Howl-o-ween event brings pups and their owners together with seasonal cocktails and light fare.

Step outside the hotel and Boston’s history comes alive in ghostly ways. On the Ghosts & Gravestones Tour, you’ll climb aboard a trolley and wander through King’s Chapel Burying Ground and the Boston Common while hearing stories of restless spirits. From the echoes of the American Revolution to chilling tales along the waterfront, Boston blends history and hauntings at every corner, and staying at The Whitney puts you right in the heart of it all.

Explore Prisons, Asylums, and Stories That Won’t Stay Silent

Philadelphia’s storied past sets the stage for a Halloween full of chills. At the center of it all is Eastern State Penitentiary, where the crumbling Gothic towers host nighttime tours that explore the prison’s notorious history. Just outside the city, Pennhurst Asylum takes the fright up a notch with elaborate haunted attractions staged within the old psychiatric hospital, blending theatrical scares with authentic history.

The Rittenhouse makes an calming home base between these spine-tingling outings. Guests can retreat from the city’s darker corners into refined comfort, enjoying seasonal cocktails or an indulgent dinner before venturing back out to explore haunted cemeteries, shadowed alleyways, and guided ghost walks. In Philadelphia, the balance of luxury and legend is part of the experience, and The Rittenhouse offers both.

Discover Spooky Cemeteries and the City’s Ghostly Corners

Maryland brims with haunted history, and nowhere is it felt more strongly than in Frederick. Visitation Hotel, set within a former Catholic girls’ school, leans into its storied past with Wye Oak Tavern’s Killer Cocktails and the Spirits of Frederick Package, which includes tickets to the city’s famed ghost tour. By night, guests can wander the hotel’s own historic cemetery, an evocative space that deepens the sense of time and memory surrounding the property.

In Annapolis, the waterfront comes alive after dark with ghost tours and haunted pub crawls that reveal tales of colonial spirits and seafaring legends. Annapolis Waterfront Hotel positions guests right by the harbor, where cobblestone streets and flickering lanterns set the tone for a night of storytelling and spectral encounters. Whether in Frederick or Annapolis, Maryland offers a haunting mix of history and hospitality.

Haunted Rooftops, Tarot Readings, and Halloween Revelry

The nation’s capital carries its own share of eerie lore. Capitol Hill Hotel invites guests to step into that atmosphere with its Capitol Haunts Package, pairing stylish accommodations with a guided ghost tour through the city’s most storied neighborhoods. Families can also enjoy the Little Spooks Parade, a cheerful community event filled with costumes and treats.

Nearby, Hotel Madera in Dupont Circle keeps the spirit alive with a full slate of programming, from the Ghostly Getaway Package (including tickets to a local ghost tour) to Halloween brunches, themed cocktails, and even pumpkin lettering classes. Meanwhile, The Morrow Hotel turns the season into an immersive experience with rooftop tarot readings, a murder mystery dinner, and lobby trick-or-treat stations. Together, these hotels create a dynamic way to enjoy both the history and revelry of Halloween in D.C.

From Masquerades to Coastal Legends, the Season Comes Alive

In Key West, every street corner tells a ghost story. Guests at Parrot Key Hotel & Villas can join the island’s Ghosts & Gravestones Tour or seek out local legends like Robert the Doll at Fort East Martello Museum. With four sparkling pools and villa-style accommodations, the resort blends the island’s sunny charm with just enough seasonal spook.

Up the coast, Cadillac Hotel & Beach Club in Miami Beach serves imaginative Halloween cocktails — think shimmering Negronis and smoky bourbon creations — while the city itself offers haunted landmarks from the Biltmore Hotel to the Deering Estate. In Delray Beach, The Ray Hotel hosts its annual Halloween Masquerade Party, complete with a DJ, themed drinks, and lively energy that turns the season into a full-on celebration.

Where Foggy Shores Meet Killer Cocktails

The California coast may be better known for its beauty than its hauntings, but Monterey has its share of ghost stories. Guests at The Sanctuary Beach Resort can sip seasonal cocktails at Salt Wood Kitchen & Oysterette before venturing into town for ghost walks that explore historic adobes and tales of restless spirits from the region’s past. With its windswept beaches and dramatic coastline, the setting itself feels otherworldly, the perfect backdrop for a Halloween escape.

Día de los Muertos, Desert Legends, and Haunted Historic Sites

In El Paso, Halloween blends seamlessly into Día de los Muertos. At The Plaza Hotel Pioneer Park, Ámbar Restaurante marks the season with a decorated altar, festive cocktails, and a mariachi performance on November 2. From October 24 to November 9, the hotel’s public spaces become a canvas of color and remembrance, connecting guests to the region’s cultural traditions.

For those who prefer their thrills darker, Concordia Cemetery, resting place of over 60,000 souls, is said to be haunted by the “Lady in White.” Guests can also join a ghost tour that visits the De Soto Hotel, Plaza Theater, and other sites rumored to harbor restless spirits, offering a mix of chilling stories and local legend. 

From Boston’s cobblestones to El Paso’s desert cemeteries, Independent Collection Hotels & Resorts offer more than a place to stay; they’re your entry point into the legends and local traditions that make Halloween unforgettable. This October, every destination pairs rich history with seasonal events, so your escape is as spirited as it is memorable.