Outdoor Date Ideas: Holiday Season Edition

fall and winter dates
After enduring the ruthless summer, fall offers a welcome solace and brings with it a whole array of outdoor activities that aren’t available any other time of the year. Unlike weekends in less eventful months, November and December do not involve Saturday afternoons looking at your partner and asking, “What do you want to do?”

The only challenge you might have is choosing one activity. That’s why I’ve created this handy guide to holiday season outdoor date ideas.

Fall and Winter Outdoor Date Ideas

Pumpkin Patch

The pumpkin patch is the prototypical November outdoor activity. A few advantages make it a particularly nice option in certain situations. For example, if you don’t have all day, many pumpkin patches are in suburbs that closely surround cities, if not directly in the city themselves. So take a break from your Breaking Bad marathon to get out of the house and get some fresh air.

Who it’s best for:

The pumpkin patch is a perfect activity for children, so why not take a trip the next time you’re babysitting your girlfriend’s nephew? You and your partner can take a crisp fall stroll while the kids burn a little energy. This family-friendly environment might also be a good place to go with your boyfriend or girlfriend’s family after dinner.


While you might have to wait for the necessary weather conditions, sledding is a traditional date idea and has been around so long for a reason: it’s a great activity to keep things interesting while also getting a little bit of exercise in this otherwise lethargic season.

Who it’s best for:

Sledding is a good activity for a couple in any stage of a relationship, but is particularly fun for a new couple that’s been together for a few months. There’s a fun, no-pressure environment, but it sometimes requires teamwork, so it’s a good way to get to know someone better.

Football Game

Football games are one of America’s favorite holiday date ideas. Personally, I’m happy anywhere you’re allowed to eat and drink all afternoon while watching a bunch of guys run around in tights.

A football game is a good time to get a group of friend together as well or go on a double date. But here’s a pro tip: if you’re going on a date to a football game, clear your calendar for the day because these things take awhile.

Who it’s best for:

Football games are one of those date ideas that are great no matter what stage of the relationship you’re in. If you just started dating, it’s an exciting opportunity to cuddle up, but also not be too serious and have a little fun. If you’re in a long term relationship, it’s a nice way to spend several hours together doing something that you likely don’t do every weekend.

Football is also a perfect idea for a first date (maybe with dinner or hot chocolate afterwards). You have something to watch in the event that you guys don’t particularly hit it off or want to stare into one another’s eyes for hours. And if you do hit it off and want to have some conversation, it’s still acceptable to do that during a football game, whereas the same can’t be said for a movie or even a concert.

So stop reading this right now and buy some tickets online for a game near you!


Ah, ice-skating. Is there a more stereotypical and timeless date idea than this during the holiday season? A blushing couple in love, holding hands and gliding across the ice, spinning around in circles in the middle of the rink and helping each other up when one of them falls? I think not.

Who it’s best for:

Ice-skating is a good environment in which to have conversation without too much pressure, plus it’s always a somewhat different activity as few people go ice-skating on a regular basis.

So why not? YOLO. Get out there and have a little fun!

Outlet Mall Shopping

Love man and woman embracing outdoors winter snowfall
Hear me out on this one. While it’s true that shopping is not generally considered an activity for couples, shopping practically becomes a sport during the Christmas season. Whether you enjoy shopping or not, it’s nearly impossible to avoid hitting the outlet malls, even for those who are determined to finally reach their goal of doing all the Christmas shopping on Amazon this year.

Who it’s best for:

Outlet mall shopping is not an activity to be taken on by the couple who is casually dating. This is the case for at least two reasons:

1. Christmas shopping brings up a lot of emotions. It requires that you assess your relationships with family, friends, and SOs to determine what level of gift to get them (or whether to get them one at all). If that isn’t a recipe for stirring up repressed emotions and causing fights between couples in public places, I don’t know what is.

2. I mean, have you ever BEEN shopping on Black Friday? You risk your life going in there. At the very least the two of you are going to need a strategy for getting past the crazies and getting to that plasma screen TV.

To be sure, this high-pressure date idea is not for the faint of heart. Only go outlet mall shopping if you guys are pretty much in it for the long haul.

Fall Festival

Whatever outdoor festival is in your area, it’s bound to be interesting, and there’s a good chance it’s a festival that you haven’t been to before. If you live in a large city, there are probably several outdoor festivals in your area to choose from. Maybe this week there is a fall beer festival, while in a few weeks, there’s a hayride festival in a neighboring suburb.

If you don’t have the time to do them all, pick one that seems interesting or that you haven’t been to yet, then grab your partner to come along for the ride!

 Who it’s best for:

Fall festivals are a wonderful time for first dates or new couples who have been together for just a few weeks to a couple of months. All the stimulation offers countless conversation starters. Plus, it’s a great way to learn more about a person whom you don’t know very well.

Which Fall Outdoor Date is Right for You?

If after reading the above guide, you still aren’t sure how to spend next Saturday afternoon with your love, I’ve put together this little quiz to help you figure out which activity is right for you.

1. When you’re on a date with a new guy, which kind of arrangement makes you most comfortable?

a. I want to do as little physical activity as possible to reduce my changes of tripping on something.

b. I prefer to be active because it takes the attention away from any potential lackluster conversation.

c. I’m most comfortable after a cocktail or two to ease the awkwardness of those early dates.

2. Which reality TV show can you see you and your SO doing?

a. The Amazing Race

b. Survivor

c. House Hunters

3. What’s your favorite holiday rom com?

a. Love Actually

b. White Christmas

c. Ew, Rom Coms? Puke.


  1. a=2, b=1, c=3;
  2. a=2, b=3, c=1;
  3. a=2, b=1, c=3.

Now, add your points together. If you got:

3-5 points:

You’re a Classic Christmas!

You like to get moving on your dates and keep things traditional. You might best enjoy spending an afternoon or evening going ice-skating and hitting Starbucks afterwards. Otherwise, take a trip to the pumpkin patch and bring your pet if you have one to make it extra fun!

6-7 points:

You’re a Festive Dater!

You like to keep things interesting but prefer not to get too wild. Try taking the challenge of going to every holiday festival in your area over the next couple of months. Bring some friends or family with you too! You might also enjoy trekking up a big hill and spending an afternoon sledding with your love.

8-9 points:

You’re on Santa’s ‘Naughty’ List!

You definitely need to steer clear of the Pumpkin Patch unless you and your boy toy want to take shots of spiced rum first. An ideal date for you would be going to the football game where you can scream your ass off.

Or, try going outlet mall shopping, which is a great place for you to take out your aggression on pushy holiday shoppers and create an awesome game plan for you and your date to execute (probably flawlessly).

If you have the time, try each of these activities and see which ones suit you and your partner best. This holiday season, limit the number of holiday blockbusters you see at the movie theater, and instead get outside. Whether you’re into sporty dates or prefer to stick with the classics, this is a magical season. Get out there and enjoy it!

Leave a Reply

Your email address will not be published. Required fields are marked *


written and researched by

You might also like…


Our trusted partners