Boston & Salem, Massachusetts

History with a haunted edge

If Halloween had a capital, Salem would be in the running. October’s Haunted Happenings bring parades, psychic fairs, house tours and cemetery walks—and it’s effortless to pair Salem days with Boston nights. Commuter rail from Boston’s North Station reaches Salem in about 30 minutes, and the seasonal Salem Ferry can sail you there in under an hour, so guests can enjoy the spectacle without wrangling a rental car.

Where to stay: Boston Harbor Hotel

A Forbes Five-Star, AAA Five Diamond waterfront icon on Boston’s Rowes Wharf with harbor-view rooms framed by the property’s signature arch. Guests can linger over seafood at Rowes Wharf Sea Grille and stroll the Harborwalk before turning in. Its North End and North Station access keeps Salem day trips simple.

New Orleans, Louisiana

America’s spookiest city, period

New Orleans makes Halloween feel inevitable: gas-lamp alleys, above-ground cemeteries and a culture that throws world-class costume parties. Expect ghost and graveyard tours nightly and a full calendar of Quarter-wide festivities each October. Come for the pageantry, stay for the music and late-night people-watching.

Where to stay: The Old No. 77 Hotel & Chandlery

Exposed brick, local art and an easy stroll to the French Quarter deliver character with convenience at this hotel in the city’s Warehouse Arts District. The building’s merchant past shows up in curated details and rotating exhibits. You’re close enough to the action to walk, yet far enough to sleep.

Manchester, Vermont

Postcard foliage with family-friendly frights

Manchester is peak New England: fiery maples, village greens and small-town Halloween traditions. History runs deep here, with 18th- and 19th-century architecture in town and nearby Revolutionary War landmarks like the Bennington Battle Monument. Families can count on trunk-or-treats, parades and arts-center events each October, with the pop-up haunted houses also in the mix. While days skew cozy with cider mills and farm stops, nights can go delightfully spooky.

Where to stay: The Equinox Golf Resort & Spa

A 1769 grande dame in Manchester Village with classic clapboard charm and modern comforts. On-site adventures—from the Land Rover Experience to hiking in Equinox Preserve—add daytime thrills to balance the ghosts. Fireplaces, a full-service spa and mountain views handle the unwind.

Lake Arrowhead, California

Classic trick-or-treat by the lake

An easy mountain escape from Southern California, Lake Arrowhead is just 2 hours from L.A. and goes all-in on family Halloween fun. The Village hosts costumed kids, candy stations and live performances (including a Thriller dance show). Mornings are for misty shoreline walks and pine-scented trails. It’s wholesome, photogenic and low-stress.

Where to stay: Lake Arrowhead Resort and Spa

Lakeside rooms, a private beach and dock, and the Spa of the Pines dial up the cozy. Bin 189 covers hearth-side dinners and lazy brunches. Quiet nights, crisp air and a hot tub soak set you up for another pumpkin-packed day.

Jackson Hole, Wyoming

Small-town charm with cowboy comfort

In late October, Jackson dresses up its antler-arched Town Square for community parties and trick-or-treating—easy to pair with wildlife-spotting in Grand Teton by day. Expect golden aspens, cool temps and Western-rustic storefronts that lean into the season. It’s the sweet spot for travelers who want fall color with their Halloween.

Where to stay: Snow King Resort

Steps from Town Square, at the base of Snow King Mountain, with a heated outdoor pool and hot tub that shine on crisp nights. Grand View Spa handles post-hike recovery, while rooms and luxury condos make bringing the whole crew convenient. Views of the Tetons are the bonus.

Newport, Rhode Island

Gilded Age mansions after dark

Newport’s iconic “cottages” embrace spooky season with myriad activities, including a pumpkin patch at Trinity Church Newport (packed with more than 1,000 pick-your-own pumpkins, gourds, mums, and more) and a group paranormal investigation through the living quarters and dark corners throughout Historic Fort Adams. Add moonlit harbor strolls, cozy taverns and coastal drives to leaf-peep your way through the Cliff Walk. The vibe is more elegant-eerie than jump-scare.

Where to stay: Wayfinder Newport (North End)

A design-forward boutique stay with local art, welcoming common spaces and on-site food and drink. It’s a convenient launch pad for mansions, harbor, beaches and that golden-hour sail. Park once, then explore at an easy clip.

Explore the more than 50 distinct, independent properties that are part of the Benchmark Resorts & Hotels portfolio, a collection 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.