If cocktails and popsicles had a very Midwestern baby, these would be it. Easy Frozen Old Fashioned Treats taste like your favorite happy-hour sip fell into a snowbank and decided to stay. We’re talking orange, cherry, a whisper of bitters, and a very polite amount of bourbon—all frozen into slushy cups or pops that make summer feel smug. They’re make-ahead, scandalously simple, and the freezer does all the hard work while you act like you meant to be this organized. Yes, I’m calling them “Easy Frozen Old Fashioned Treats” because that’s exactly what they are, and also because I will not be taking notes from anyone who suggests I “just use fewer dishes.”

Last weekend I thought I’d be festive and make a batch “for later.” My husband heard “taste test” and went full lab coat, which is a bold look for someone who once burned water. Every 20 minutes he opened the freezer to “check the crystallization,” which I’m pretty sure is code for “I wanted another sample.” Meanwhile, the kids spotted the popsicle sticks and I had to label every cup in all-caps ADULTS ONLY like a very fun librarian. Yes, this pan is too small. No, I won’t wash fewer dishes. Grandma stopped by, took one bite, and said, “Needs more bitters.” Then she took another and said, “Perfect.” Iconic behavior.

Quick Recipe (so you can actually make the thing):
– In a pitcher, whisk 1 1/2 cups orange juice, 1/2 cup water, 1/3 cup simple syrup (more or less to taste), 1/2 cup bourbon (up to 2/3 cup for slushier), 2–4 dashes Angostura bitters, 2 tablespoons cherry juice (from the jar), a pinch of salt, and a little orange zest.
– Pour into 3-oz paper cups or popsicle molds. Add sticks after 45 minutes when semi-firm, then freeze 6–8 hours.
– For slush: pour into a metal loaf pan, freeze, and rake with a fork every hour until snow-cone vibes appear. Scoop into glasses and pretend you’re fancy.

Why You’ll Love This Easy Frozen Old Fashioned Treats

– It’s a cocktail you can eat with a stick. Chew responsibly.
– No shaker, no muddler, no “bartender elbow.” The freezer does the reps.
– Make-ahead magic: stash a tray and look brilliant when guests “just pop by” (help).
– Scales for a crowd or your Thursday. I don’t judge; I portion.
– Sweet, citrusy, a little bitter—like me when someone puts the bourbon back empty.
– Zero ice dilution. Your drink won’t turn into sad orange water.

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Time-Saving Hacks

– Use store-bought OJ and the cherry juice from the maraschino jar. Is it legit? No. Is it delicious? Absolutely.
– Microwave simple syrup: equal parts sugar and water, 45–60 seconds, stir, done. Bar snobs can look away.
– Ice cube trays work in a pinch—pop, dump in a glass, splash of club soda, pretend it’s “granita.”
– Metal pan = faster freeze. Glass = patience you don’t have.
– Forget measuring spoons. The cap of the bourbon bottle is a totally real unit of measurement in this house.

Serving Ideas

– Slide a pop into a rocks glass with a splash of club soda. Congratulations, you invented “lazy spritz.”
– Sprinkle with crushed pretzels or flaky salt for that classy bar-snack energy.
– Serve with wine if the kids drove you nuts. I don’t make the rules; I merely thrive within them.
– Keep it simple: pass the cups on the porch and let the drips water the herb garden. Nature’s garnish.

What to Serve It With

– Salty snacks (kettle chips, roasted nuts, pretzels) so the bourbon has friends.
– Backyard basics: brats, burgers, grilled corn slathered in butter your cardiologist can’t see.
– Charcuterie if you need it to look like a “spread,” not a coping mechanism.
– Bubbles: club soda with lime or a cheap Prosecco splash if you’re feeling plucky.

✔Tips & Mistakes

– Don’t over-booze it. Keep it around 1/2 cup bourbon per batch or it won’t freeze—just sadly slush forever.
– Too sweet? Add a squeeze of lemon or an extra dash of bitters. Too bitter? More simple syrup. Balance like a tightrope walker with snacks.
– Label the cups. If your kids can read, add a skull doodle. If they can’t, add extra skulls.
– To unmold pops, run warm water over the mold for 10–15 seconds. Don’t yank like a lawnmower.
– A tiny pinch of salt makes the flavors pop. Science, but make it tasty.

✔Storage Tips

Store it in the fridge… if there’s any left. Cold midnight leftovers? Sometimes better than fresh.
Keep covered in the freezer for up to 2 months. Let sit at room temp 3–5 minutes before serving so they’re not brick-like. If it goes slushy, call it granita and act smug.

✔Variations and Substitutions

– Wisconsin-style: swap bourbon for brandy, add a teeny splash of lemon-lime soda to the mix for sweeter vibes.
– Smoky campfire: add 1/2 teaspoon maple syrup and a drop of liquid smoke. Tiny drop, not a bonfire.
– Citrus boost: zest the orange straight into the pitcher for extra perfume.
– No alcohol: use black tea or strong orange-spice tea instead of bourbon, a little extra bitters-like flavor with orange extract. Still fun, fewer questionable texts.
– Sweeteners: sugar ↔ honey ↔ maple. If it dissolves, it qualifies.
– Bitters bar: Angostura is classic, orange bitters are bright, chocolate bitters are “I have a personality” in a bottle.

Frequently Asked Questions

I can’t have gluten… will this still work?

Yep. Use tamari or coconut aminos. You’ll survive and still brag about it online.

Do I have to peel the pineapple first?

Unless you enjoy chewing bark… yes, peel it. Your teeth will thank you.

Can I use canned pineapple instead of fresh?

Sure. Just drain it well or enjoy syrup soup. Still tasty, though.

How sweet is this? Can I tone it down?

Absolutely. Cut the sugar—or don’t, and embrace the sugar rush.

What if I skip the sesame oil?

Then you’ll miss the nutty vibe, but relax—it’s still food. You’ll live.

Remember it later

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