Fall in New England is the best, with crunchy leaves, perfect sweater weather, and one of our favorite holidays, Halloween. There's no better place to celebrate fall than Portland, with its quintessential New England seaside city vibe and lots of fun happenings during October (not to mention our cozy boutique hotel). We love these unique Halloween events in Portland—a great way to explore the spooky side of Portland while learning about the city's history. Check out these historic Halloween events in Portland on your next visit this fall.
This historic cemetery is hidden in plain sight on the eastern end of Congress Street. Open select hours for guided tours and exploring, Eastern Cemetery is the oldest historic landscape in the city dating back to 1668. You'll find the graves of ship captains that died in the War of 1812, family of Portland's famed poet Henry Wadsworth Longfellow, and even women with connections to the Salem Witch Trials. Come mid-October, the nonprofit Spirits Alive puts on Walk Among the Shadows, an after-dark tour that tells tales of the city's supernatural activities. The tours are guided through the cemetery where groups will encounter actors recounting stories of ghost ships, sea monsters, and strange sightings. The tour is not scary, but rather entertaining and educational. Tours are offered twice a night October 19-22 and 26-29 and tickets are $10 for adults.
The childhood home of one of the city's more famous residents offers Halloween events in Portland with a haunted house tour. Inspired by Longfellow's poem Haunted House with the line "All houses wherein men have lived and died are haunted houses," the hour-long tour tells the tales of residents that have died in the house...and who maybe still linger. Led by longtime docent and Longfellow impersonator James Horrigan, this tour is a great way to see the Longfellow House with some spooky tales. Tours are held daily October 25-30 (excluding Sunday) and tickets are $15.