Halloween on Pittsburgh’s North Side

With Summer officially closed in Western Pennsylvania and autumn ushering in more regimented schedules, this year Halloween offers a family-friendly Friday night opportunity to let loose a little. But be ready for anything! In late October, Pittsburghers know to prepare for a range of trick-or-treating temperatures. They keep long johns on hand for an underlayer, an umbrella at the ready, and either cozy boots for warmth or strappy sandals to beat the heat.

A Look at the Pittsburgh’s North Side Halloween Celebrations

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Regardless of weather, Halloween unfolds on the North Side of Pittsburgh in a most celebratory way. Here, it has become a nod to neighbors and individuality. It’s an invitation to create and be creative, an excuse to break bread as backyard grilling gives way to comfort foods, and even an opportunity to appreciate the enduring architecture in the old homes unique to many of Pittsburgh’s neighborhoods.

Haunted mansion vibes abound on the North Side, making it a perfect Halloween backdrop. Neighbors look forward to the yearly tradition of walking the streets in Observatory Hill and Perry Hilltop. Sidewalks throng with adults with warm drink in hand. Plus all ages of children walk with ever expanding bags of treats slung over their shoulders.

How to Start Halloween in the City

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Most years, prior to go-time, locals will haul pots of chili, chicken tortilla, and black bean soups, as well as a batch of homemade breads to Halloween homebase – aka, the residence of photographer Katie Long. A variety of mulled wines and spiked ciders will warm in crockpots as a little something to nip the chill for chaperones as the sun dips below the skyline.

Between 5:30 and 7:30PM, a golden hour casts gentle autumn shadows. Vibrant costume fabrics play well against the hyper color of maples and ginkgoes and age-old oaks. Stiff cardboard DIY ensembles that speak to hours of assembly envelope wee trick-or-treaters. Delight is in the air. Halloween here is a family affair, with room for all personalities.

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A few folks man the front door and distribute goodies while watching the festive scene evolve. Others join the door-to-door adventurers – some with calculated routes for visiting favorite neighborhood homes known as the biggest candy bar givers and scariest house drapers. Children and adults alike enthusiastically join the impromptu parade, often collaborating with team concept costumes – Harry Potter’s posse, a band of Barbies, the quartet of seekers from The Wizard of Oz, or a coven of traditional All Hallow’s Eve ghouls.

Don’t Stop the Party After Trick-or-Treating

When the trick-or-treating window set by the city has passed, friends refuel with easy-to-heat one pot stews. The kids indulge in the age-old tradition of trading candy. Two by two and five by five, they congregate on the porch, laughing well past bedtimes. Conversation runs the gamut from costume successes and malfunctions to hot glue gun injuries. Tips are traded for making next year’s carboard suits of armor and optimizing future candy collecting.

It is no surprise that like Observatory Hill, North Side neighborhoods throughout – Brighton Heights, the Mexican War Streets, Manchester, and Spring Garden – have fostered growing collective traditions on Halloween night. These cityscapes don their own disguises, easily transforming into the perfect moody backdrop. Their walkability, fitting urban architecture, and communal spirit have grown these highly anticipated traditions for celebrating more than meets the eye.

Story by Leah Hohman Esser
Photography by Katie Long

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