Credit: CP Illustration: Sam Schaffer

Every fall, like clockwork, Katie Heldstab and her wife, Christa Puskarich, the couple behind Leona’s Ice Cream, load up their truck and head north. They drive to a little town called North East — yeah, confusing, but it’s in the northwest corner of Pennsylvania. It’s the tail end of the harvest season, and winemakers are knee-deep in Concord grapes, hands stained purple, as they hustle to get the last of the crop. Heldstab and Puskarich are right there with them, filling their truck with hundreds of pounds of perfectly ripe grapes, all while keeping an eye on the clock for their mandatory Lake Erie coffee stop.

Heldstab calls ahead to Orton’s Fruit Market, timing their trip perfectly — usually late September through mid-October — to make sure the Concord grapes are ripe and ready.

Back in Pittsburgh at Leona’s, those grapes are turned into an ice cream that’s pure fall in a pint — deep, tangy, and bursting with flavor. But here’s where it gets even better: they sandwich that rich, purple goodness between crisp peanut butter cookies. The result? A fall-inspired PBJ ice cream sandwich that’s sweet, spiced, and cool — a perfect embodiment of what I like to call Ice Cream in a Jacket season around here.

“We love our summer crowd,” Heldstab says, “but there’s something extra special about the folks who stick with us through the slow season. That’s why we offer flavors you can only get in the fall and winter. It’s part seasonality, part reward for our loyal winter ice cream fans.”

When they’re not grabbing Concord grapes in North East, Pa., they’re hitting Triple B Farms for apples, strawberries, and raspberries or scooping up plums and pears from Pletcher’s Farm Market in Champion. Each haul fuels their seasonal ice cream magic.

The folks at Millie’s lean into that magic, too. As Brand Director Jessica Suskin puts it, “Making ice cream in the off-season is a ton of fun for us — fall, winter, and holiday flavors are an exciting challenge because we want the ice creams to feel familiar and relevant to the season without being predictable or stale. It’s a fun annual exercise.”

But at the end of the day, it’s tough for an ice cream shop when the weather turns cold.

“We’re lucky to have our bakery keeping things steady in the colder months,” says Elias Wilson, president at Glen’s Custard, “but I’d love to see more folks supporting their local shops during this time. A cold treat in winter has its own charm. Plus, it’s always fun to see how creative people get with flavors — everything from spiced pumpkin to peppermint swirl. It’s a different vibe, but just as delicious.”

So now that fall is here (and winter is knocking), if you think it’s time to put the ice cream away, you’re seriously missing out. Ice Cream in a Jacket season is when you can savor the cold stuff while wrapped up like a burrito. Forget tricks, let’s get straight to the local treats.

Treat U-Self ice cream from Millie’s Credit: Photo: Courtesy of Millie's

Millie’s Homemade
Multiple locations
Trick or treat? Why not both? Millie’s is whipping up Treat U-Self — Rice Krispies Treats® mixed with white chocolate and buttery goodness, all folded into spooky purple ube ice cream. And don’t miss their dairy-free Ghostly Grasshopper — mint gelato loaded with crushed Hydrox cookies, no real insects involved. Millie’s folds in new flavors every month, and while they’re holiday collection is under wraps, Suskin says they’re reupping their partnership with Eat’n Park “in a way that’s sure to please nostalgic yinzers everywhere.”

Bay Leaf Cheesecake ice cream from Jeni’s Credit: Photo: Courtesy of Jeni's

Jeni’s Splendid Ice Creams
173 Bakery Square Blvd, Bakery Square
If pumpkin spice gives you the heebie-jeebies, then Jeni’s fall collection is a safe space for you. Get ready for the Bay Leaf Cheesecake, a creamy, savory delight. Then there’s the Sweet Potato Marshmallow Praline; it’s like sweet potato casserole but in ice cream form. Seriously, you might be tempted to ditch the pie this year. (Just kidding. Don’t be that person.)

Brr-Kee’s Homemade Ice Cream
539 Allegheny Ave, Oakmont
Over at Brr-kee’s, the Cinnamon-Spiced Apple Sundae is basically fall in a bowl. Apples? Check. Cinnamon? Check. Whipped cream that’ll make you want to hibernate? Oh yes. It’s like someone distilled a crisp October day and slathered it over vanilla ice cream.

Rita’s Italian Ice
Multiple locations
At Rita’s, the Pumpkin Toffee Crunch Concrete mixes vanilla frozen custard, pumpkin crème, and toffee. Or go for Dracula’s Delight: a mix of vanilla and chocolate custard, gummy bears, and mini M&M’s for a spooky sweet treat.

Glen’s Frozen Custard
Multiple locations
If you’re all about that pumpkin life, Glens Custard is where it’s at. We’re talking Pumpkin Roll Sundaes and Pumpkin Custard Pies galore. And when the chill sets in, their hot chocolate float will warm your heart — or whatever’s left of it.

Mercurio’s
1335 Freeport Rd. # 2
Besides artisanal pizza, Mercurio’s is serving up plenty of fall-inspired gelato flavors. Try their Black Cherry Bordeaux, featuring cherry gelato and salted dark chocolate flakes. Don’t miss their S’mores flavor: graham gelato, mini marshmallows, and chocolate, all in one scoop. It’s giving campfire vibes in a cup.

A fall-inspired ice cream sandwich from Leona’s Credit: Photo: Courtesy of Leona's

Leona’s Ice Cream
774 Penn Ave.
In addition to seasonal scoops like maple nut and tangerine blackberry, Leona’s specializes in ice cream sandwiches. Fall flavors include plum on ginger molasses cookies and pear caramel on sugar cookies. Don’t miss the aforementioned PBJ ice cream sandwich made with Concord grape ice cream — your childhood classic reimagined as a frozen treat.