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101 Winter Date Ideas

I love going on dates – who doesn’t? I especially love going on dates during the Christmas season. Christmas time is, in my books, one of the best times of the year. Not just because of the presents and having access to all the chocolate you could imagine, but also because it is the most gorgeous time of the year! Shops are decorated in red and green, the ground is covered in fresh snow, and trees are decked out in white.

Falling in the peak of the winter season, with gleaming lights on houses and trees reflecting off of the picturesque snow, Christmas is a beautiful, happy, and celebratory time of year. It is so powerful, even Ebeneezer Scrooge could not resist its lure. I just love this time.

Even when the Christmas season is over, and the New Year celebrations have passed – winter can still be an enjoyable time of year. There are so many things to do, sights to see, and activities to take part in before the snow melts. If you are looking to try a new date idea, look no further! I have collected 101 winter and holiday-themed dates for two.

christmas date
Trans-Siberian Orchestra in 2015 

Christmas Date Ideas

  1. See a local Christmas musical or play (I highly recommend Trans-Siberian Orchestra: The Lost Christmas Eve)
  2. Visit your local Christmas market
  3. Hot chocolate + movies night (Don’t forget the whipped topping!)
  4. Go to a religious service
  5. Take a sleigh-ride if you have them in your town
  6. If not, drive around with your windows down (I’m joking!)
  7. Go thrift shopping for the ugliest holiday sweater
  8. And then go out for dinner wearing those sweaters
  9. Drive around town looking at neighbourhood Christmas lights
  10. Create your wish list together (And then go shopping together to find a DIY version of something on the list)
  11. Make a homemade Christmas gift together
  12. Check out a Christmas ballet
  13. Blast Christmas music and decorate the house
  14. Grab a glass of eggnog and discuss what traditions you want to start with your own little family
  15. Get your picture taken with Santa
  16. Take a holiday cooking class together
  17. Bring Christmas cookies to a nursing home (probably double check with the home first)
  18. Go carolling at the nursing home
  19. Play Christmas music and have a dance party just the two of you
  20. Attend a tree lighting
  21. Pick out your own Christmas tree
  22. Head to the store to find one personal ornament you can add to your tree this year
  23. Decorate the tree together
  24. See your local Christmas parade
  25. Attend the local high school’s Christmas concert
  26. Bake your own gingerbread house
  27. Decorate a gingerbread house (like mine and Tim’s first date!)
  28. Eat a gingerbread house!
  29. Make Christmas cookies
  30. Arrange a Christmas cookie exchange
  31. Wrap presents together (appreciate the small moments)
  32. Create your own Christmas song
  33. Put up Christmas lights together (sync your lights to the Harry Potter soundtrack)
  34. Invite your family over for a house lighting
  35. Play Christmas-olopy (can be found here)
  36. Make a homemade Christmas ornament
  37. Write a letter to Santa (connect with your inner child!)
winter date

Winter Date Ideas

  1. Ice Skating (like, on the Rideau CanalSkateway for example!)
  2. Volunteer with your local non-profits
  3. Cutout snowflakes together and decorate the house with them
  4. OR, go donate the decorations to a shelter, nursing home, or a school
  5. Offer to help put said decorations up
  6. Have a snowball fight
  7. Make a snowman
  8. OR, make snow angels
  9. Definitely make an igloo with recycling containers
  10. Go tobogganing
  11. Go window shopping
  12. Take wintery photos together
  13. Go to a Bed and Breakfast
  14. Even better, rent a cabin for a weekend
  15. Cuddle in front of your fireplace
  16. OR,in front of the fireplace channel
  17. Visit your family
  18. Escape the holiday madness and go to the museum
  19. Try going to the art gallery
  20. OR, the science centre
  21. OR, the aquarium
  22. Workout together
  23. Play a board game or five
  24. Share favourite holiday memories
  25. Become a hot chocolate critique and go to different coffee shops to rate their hot chocolate
  26. OR, a holiday cookie critique
  27. OR, a candy cane latte critique
  28. Make breakfast for dinner
  29. Have a fondue date at home
  30. Host a potluck
  31. Go on a Groupon date
  32. Go for a dip ina local hot spring (or hot tub)
  33. OR, have a warm bath together
goal date

The above picture is what I drew for Tim before we were engaged (using
the Paint program) to describe my goals for our life together. 

End-Of-Year Date Ideas

  1. Write a newsletter together
  2. Create your pages in the family yearbook (is my family the only one who does this?)
  3. Make resolutions for the next year
  4. Create plans for the resolution
  5. Go radio silent – disconnect from all social media, TV, etc. fora night
  6. Make a fort!
  7. Reminisce over the last year together
  8. Do a wine tasting
  9. Go cosmic bowling
  10. With champagne!
  11. Take a mini-road trip together
  12. Watch fireworks
  13. Master the perfect cocktail at home
  14. Plan a vacation you plan on taking in the New Year
  15. Go to the bookstore and find a book you want to read together in the New Year
  16. Have an indoor picnic
  17. Play tourist at a local attraction
  18. Have a Super Smash Bros night
  19. Clean out your closets together
  20. Get rid of the junk in your house (declutter for the New Year)
  21. Spend an entire day in bed together
  22. Figure out your New Year’s Eve plans
  23. Watch the ball drop and kiss at midnight!
  24. Celebrate all of the countdowns around the world
  25. And kiss after each one!
  26. Transform your home into a vacation
  27. Have an at-home spa day
  28. Dress up and head to your nearest fine dining restaurant
  29. OR, stay casual and have a dollar menu date
  30. Go out dancing together
  31. Have your own wine tasting at home



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