13 Coffee Drinks and Cookies We Save for the First Properly Cold Night

The first properly cold night is when I stop pretending an iced coffee will do and start looking for something warm to hold with both hands. That’s also when a plate of homemade cookies suddenly sounds like a perfectly reasonable dinner companion.

I like having a few coffee drinks and cookie recipes ready for evenings when the windows are closed, the kitchen feels cozy, and nobody is in a hurry to go anywhere. No elaborate dessert spread is needed, just a good cup of coffee and something sweet to break into while it’s still warm.

These 13 coffee drinks and cookies are what I’d save for that first chilly night when staying in becomes the best plan.

Tiramisu Cookies

The first cold night is when I want dessert and coffee in the same bite, and these cookies do both. They carry the coffee and cocoa flavors of tiramisu in a soft cookie you can hold in one hand. Pair them with a small cup of Colombian Cafe Tinto and let the coffee do double duty.
Get the Recipe: Tiramisu Cookies

S’mores Latte

You don’t need a campfire to get s’mores flavor on a cold night. This latte brings chocolate, marshmallow, and graham cracker into one warm mug of coffee and milk. Add a Dark Dream cookie on the side, and it’s a full chocolate night.
Get the Recipe: S’mores Latte

Colombian Cafe Tinto

Tinto always takes me right back to a foggy mountain in Colombia. It’s just strong Colombian coffee simmered in a pot with panela, an unrefined cane sugar that makes it smooth and a little sweet. One small, hot cup is all it takes to warm your hands on a cold evening.
Get the Recipe: Colombian Cafe Tinto

Pumpkin Cookies with Cream Cheese Frosting

For years, I bought a big tub of pumpkin cookies at the store every fall without thinking twice. These are soft and cakey, spiced with cinnamon, nutmeg, and ginger, and finished with tangy cream cheese frosting. Bake a batch early in the season, then pull a few out with coffee on the first cold night.
Get the Recipe: Pumpkin Cookies with Cream Cheese Frosting

Crumbl Copycat Dark Dream Cookies

Some nights only a deep chocolate cookie will do. This copycat of the Crumbl favorite is a thick, double chocolate cookie with a soft center and plenty of chocolate chips. Pair it with hot coffee or a glass of milk on a cold day.
Get the Recipe: Crumbl Copycat Dark Dream Cookies

Chai Spiced Latte with Dried Rose Petals

A pinch of dried rose petals makes an everyday chai feel a little special. Steep black tea and warm chai spices with the petals, then top with steamed milk. A Chocolate Linzer cookie makes a pretty partner for this cozy mug.
Get the Recipe: Chai Spiced Latte with Dried Rose Petals

Chocolate Linzer Cookies

Linzer cookies always look like they came from a bakery window. Two chocolate cookies sandwich a sweet filling, with a little window cut in the top so you can peek through. Set a plate out with dark coffee when the first frost shows up.
Get the Recipe: Chocolate Linzer Cookies

Gluten Free Almond Flour Chocolate Chip Cookie

Almond flour makes these chocolate chip cookies soft, tender, and gluten-free. Fresh from the oven, they’re perfect with a hot mug of coffee on a chilly night.
Get the Recipe: Gluten Free Almond Flour Chocolate Chip Cookie

Slow Cooker Pumpkin Spice Latte

Let the slow cooker handle the coffee when everyone’s home on a cold night. Coffee, milk, pumpkin, and warm spices simmer together low and slow, so you can ladle a fresh mug whenever you want.
Get the Recipe: Slow Cooker Pumpkin Spice Latte

Autumn Spice Latte

Coffee shop lattes are easy to copy at home once you have a few warm spices on hand. This one mixes cozy fall spices into espresso and steamed milk for a mug that smells like baking day.
Get the Recipe: Autumn Spice Latte

Christmas Date Cookies

Dates bring their own sweetness to these cookies, so they taste rich without much fuss. Soft and chewy, they’re a natural match for the warm spices in a Dirty Chai Tea Latte when the nights turn cold.
Get the Recipe: Christmas Date Cookies

Easy Chewy Chocolate Crinkle Cookie

Chocolate crinkle cookies crack open in the oven, and that’s the fun part to watch. The dark, fudgy dough gets rolled in powdered sugar, so every cookie bakes up with a snowy, cracked top. Dunk one in an Autumn Spice Latte on the first cold night.
Get the Recipe: Easy Chewy Chocolate Crinkle Cookie

Dirty Chai Tea Latte

When you can’t decide between coffee and tea, a dirty chai lets you have both. Spiced chai gets a shot of espresso and a pour of frothed milk, so it’s creamy, warm, and a little spicy. It’s a cozy mug for a night when the wind is howling outside.
Get the Recipe: Dirty Chai Tea Latte

What’s your first cold-night pairing: a creamy cup of coffee with a chocolate cookie, or something a little spiced and buttery?