Allie and Ethan tucked in close beneath the evergreen branches, with her black coat over a red dress. I love that little bit of red against the green. Their engagement photos have me thinking about a fall and winter date idea you could plan for your next free afternoon: a walk together, somewhere to sit, and a warm drink afterward.
Pick a place you both want to visit, put on your coats, and leave time to stop along the way. You can bring the cocoa from home or choose a coffee shop for the second half. Here’s how I’d put the afternoon together.
Start with a walk you both want to take
Choose somewhere with a route that suits both of you. A park, a few blocks downtown, or a familiar neighborhood could work. Think about where you’ll start, where you can sit, and how far you feel like walking that day.
For a date around Bolivar, Dunnegan Memorial Park’s city page lists a mile-long trail through the trees and benches where you can stop. Check current park information and conditions before heading over. You can choose a short part of the walk and turn back whenever you’re ready.
If you already walk the same route together, let one person choose a new turn. You might pass a shop window you want to look at or find a bench you usually walk past. Give yourselves room to stop when something catches your eye.
Wear the coat you’re excited to pull out again
Allie’s red dress and black coat are such a good combination. You could borrow that idea with a dress and tights, or wear a sweater with jeans and boots. A scarf you love can come along, too.
Start with the clothes you want to wear, then check that they work for the day. If you’re walking on grass or a trail, choose shoes for that ground. If your plan includes sitting outside, bring the layer you’ll want once you stop moving.
Before you leave, check the forecast. The National Weather Service’s cold-weather planning guide recommends checking conditions and dressing for the outdoors. For this date, I’d keep the warm stop nearby so you can head inside when you feel like it.
And yes, the gloves can go in the coat pockets now. Future you, holding a warm cup, will have enough to carry.
Leave room to sit together
The seated portraits in Allie and Ethan’s gallery are a lovely part of the inspiration here. Find a place where you can pause and talk for a while. A dry bench works, or you could bring folding chairs if the place allows them.
If you like the idea of a blanket, bring one you can use outdoors. Check the seat or ground before setting it down. You can also save the sitting part for a table inside the coffee shop.
This is where I’d leave the schedule open. You might talk about the movie you watched last night, point out a dog walking past, or decide what sounds good for dinner. Let the conversation go where it goes.
For a longer stop with food, our picnic afternoon at Dunnegan Park has a few things to think about bringing. A whole lunch is optional for this outing. Two drinks and a walk can fill the time you have.
Pick your warm drink before you leave
Choose whether you want to carry a drink or sit down for one afterward. If you’re bringing something from home, use a leakproof flask and pack the cups you need. Cocoa, coffee, tea, and warm cider are all options. Each person can bring what they like.
For a coffee-shop stop, check the current hours before you plan around it. Look at how long it takes to get there from your walk, too. You can order a drink each and choose something from the pastry case if you’re hungry.
I like the idea of each person picking one part of the date. One chooses the walk; the other chooses the drink stop. If you both have a place in mind, save the second one for another afternoon.
Make it a fall date or a winter date
In fall, you could take the longer route, stop to look at the leaves, and bring a snack to eat outside. Pick a time with enough daylight for the walk you want to take. Fall color changes from place to place, so enjoy what’s there when you go.
For winter, I’d plan the indoor stop first and build a short walk around it. A few blocks before coffee can be plenty. If the paths are icy or the weather turns, meet inside and keep the afternoon together on the calendar.
You can bring a small card game to play at home afterward, make cocoa in your own kitchen, or choose a film together. Ask which part sounds good to both of you before you pack a bag full of plans.
A fall and winter date idea you can put on the calendar
Here’s one way to plan it. Adjust the times to fit your day:
- Meet in the early afternoon with coats and walking shoes.
- Take a short walk, with time to look around or stop at a bench.
- Head to the warm place you chose for drinks and something to eat.
- Leave the rest of the afternoon open, or pick a movie for later.
For a date with very little to pack, I’d bring a phone, keys, gloves, and whatever you need for your drinks. Add a blanket only if you plan to use it. If you’re taking your own food, pack it for the time and place you’ll be eating.
A message like this gives the other person something to say yes to: “Want to go for a walk Saturday afternoon and get hot chocolate afterward? I’ll choose the walk if you choose the hot chocolate.”
If you’d like to plan portraits together on another day, our engagement photo ideas guide covers outfits, places, and things to try during a session.
For this afternoon, I’d start by finding that coat and sending the text.
