Halloween looks to be back in full swing this year, after 2020 and 2021 were severely toned down by COVID-19. Now that Portland’s long stretch of warm weather seems to be coming to an end, it’s finally time to get in those crunchy leaf vibes and indulge in some tricks and treats. Whether you’re an all-out costume partier or a “carve pumpkins at home” type, this list dives into the various ways Portlanders can celebrate Halloween with food and drink, from dessert specials to full-blown events.
The dessert shop from Holler Hospitality, the restaurant group behind Holler and Bullard, is offering three “scary delicious” ice cream pints for the season: Caramel Apple Sorbet, Halloween Candy, and Pumpkin Chip. The treats are available for takeout and in-house orders only.
Every year, the creative confectioners at Portland’s iconic ice creamery Salt & Straw come up with something to fit the spookiest holiday. This year, diners can find ice cream flavors like Don Bugito’s Creepy Crawly Critters, a matcha ice cream with toffee-brittle mealworms and chocolate crickets; Jack o’ Lantern Pumpkin Bread with whipped cream cheese frosting; and the candy-filled butterscotch ice cream the Great Candycopia. The specials will be available in scoop shops across town through the 31st.
This snack shop is a staple of East 28th’s Restaurant Row, and its monthly sundae specials have gained a cult following on social media. October’s offering is the Eye Scream Sundae: layers of vanilla soft serve, “purple witch goo” (a.k.a. ube pudding), chocolate cookie “dirt,” raspberry “blood,” and an eyeball gumball.
This pie shop, with locations in Kerns and Montavilla, is currently serving two treats for vampire lovers: Die Crust Cinnamon Rolls made with charcoal pie crust, cinnamon butter, and a blood-red cinnamon glaze, and the pitch-black Chocula S’Cream Pie.
For those looking for N/A beverages on the spooky side, the Clinton Street Coffeehouse has Halloween sprinkle-topped candy corn lattes, pumpkin cream cold brews, and golden maple tea lattes all month long. Grab one before a horror movie at the Clinton Street Theater.
Woodlawn Coffee and Pastry, Miss Zumstein Bakery & Coffee Shop, Saint Cupcake, and Helen Bernhard Bakery
The sweets at these Portland bakery standbys get a spooky makeover in the month of October, with sugar cookies shaped like pumpkins, cupcakes sprinkles with every possible shade of orange, black, and purple, and layer cakes decked out with spiderweb and ghost designs through the 31st.
Pop-ups and Parties
Jupiter Hotel’s cocktail bar Hey Love is host to the Portland location of this nationwide Halloween-themed bar pop up. Expect an immersive transformation of the space with skulls and coffins, plus themed food and cocktails like the “Hellraiser” (Hornitos, Chairman’s Spiced Rum, Cointreau, and spiced oat orgeat). It runs now through the 31st.
The urban winery Hip Chicks Do Wine has been running the same Halloween special for years, and it’s always a fun time — visitors can find a special flight of five wines, each paired with a Halloween candy. It also includes a taste of the winery’s Halloween Witches Brew Sangria. The pairing is available only on weekends: October 21st to the 23rd, and October 28th to the 30th. Reservations are required and can be made online.
This dive-bar-diner (one of Portland’s rare places to eat past midnight) has been doing a month-long series of cocktails themed to horror movies playing at the Clinton Street Theater across the street. Upcoming drinks include “The Beast” for the Mandy showing on October 22, “The Lady in the Radiator” for Eraserhead on October 27, and the “Silver Bullet and Fire” for The Howling on October 28.
The former food cart, which recently pivoted to catering and pop ups only, is bringing a Halloween-themed CBD-infused pop up to Mestizo on Sunday, October 23rd, with seatings at 5 p.m. and 7:30 p.m. The $60 gluten-free menu will include pumpkin spice chicken wings, a seasonal “Frankensalad,” and a cherry cobbler called “Mummy’s Sweet Revenge.”
The elegantly vintage cocktail lounge at the Woodlark Hotel will host a Halloween party on Saturday, October 29th with DJ Aquamarine and themed cocktails.
At 1 p.m. on Sunday, October 30th, this iconic dive bar will host a “pup strut” costume contest for dogs, benefitting Portland dog rescue Stumptown Strays. The bar will be pouring beer and slinging fried chicken and jojos, with an auction, raffle, and prizes for the coolest costumes.