It's October, and Halloween is on the horizon. Large spiders and cobwebs cover landscaping, skeletons are perched in shadowy windows, and jack-o'-lanterns sneer at passers-by from porches. Celebrate the spookiest day of the year by traveling to one of the country’s most haunted cities, where you can soak up eerie historical facts and rendezvous with apparitions. The stops in each city are rated on a scale of 1 to 5 howls, with 5 being the creepiest.

First up is haunted Portland.

Have Dinner with a Specter

Old Town Pizza
226 Northwest Davis Street

You might feel someone standing near you as you chow down at Old Town Pizza. The restaurant, built in 1974, sits in what used to be the lobby of the Merchant Hotel. The well-known haunted hotel opened in 1880, and a woman named Nina worked there as a prostitute. It’s said that she leaked info on local delinquents to the authorities, and the unhappy hoodlums pushed her down an elevator shaft. Today, customers report seeing a woman in a black dress passing by their tables.

Level of creepiness: 2 out of 5 howls

Hang Out with Two Spine-Chilling Moviegoers

Hollywood Theatre
4122 Northeast Sandy Boulevard

10- to 15-minute drive from Old Town Pizza
Time commitment: dependent on the movie

Head to the Prohibition-era Hollywood Theatre to catch a flick with two of its spooky customers. While you’re waiting for buttery popcorn, look for the male specter who hangs out in the lobby. Be sure to grab a seat early—the theater’s female apparition likes to sit in the back rows.

Level of creepiness: 3 out of 5 howls

Hunt for Ghosts

Portland Walking Tours’ Beyond Bizarre Ghost Tour
Meet at former Merchant Hotel building, 131 Northwest 2nd Avenue

10-minute drive from Hollywood Theatre
Time commitment: less than 2.5 hours (7 p.m. tours are family friendly; 10 p.m. tours are for adults only)

A ghost expert and a clairvoyant helped create this nighttime tour of Old Town Chinatown, where you’ll learn how to use ghost-hunting equipment. After visiting haunted historical sites, you’ll get another chance to meet Nina when you delve into the tunnels running below the old Merchant Hotel. Try not to be scared by your own shadow.

Level of creepiness: 4 out of 5 howls

Sleep at a Haunted Hotel

The Benson Hotel
309 Southwest Broadway 

5-minute drive from the Merchant Hotel building

The concierge may not admit to this, but The Benson Hotel, founded in 1913, has made folklore with its ghastly guests who just can’t quite leave. Request a room on the ninth floor and you might come face to face with a presence who has quite an Internet presence: a Yelp page dedicated to him. As you climb the lobby stairs, keep an eye out for a male specter. Spirits have also been seen at one of the hotel’s restaurants.

Level of creepiness: 5 out of 5 howls

Photos: Portland City Walk 2012 – 34 by Kabayanmark Images under CC BY-ND 2.0; Hollywood Theatre, Portland Ore – Edited by Colby Aley under CC BY-ND 2.0; Portland, OR by Herb Neufeld under CC BY 2.0; The Benson Hotel lobby by Samantha Marx under CC BY 2.0 

Check out more spooky reads:

Six Hotels We're Pretty Sure are Actually Haunted

The The Guide to Halloween