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Enjoy apple season: I've enjoyed a great number of fall and early winter months picking apples with friends or on a date, or attending an apple festival in a smaller community with many different varietals to choose from. Alternatively, you could go and pick apples, and then learn how to make a pie out of them, either by perusing some of our lovely Food guides suggestions, or by taking a class together.
Go ice skating: See if there's a rink that's only open during the colder winter months nearby, preferably with some roasted chestnuts available, or at the very least a thermos of hot chocolate to warm up with afterward.
Explore a new winter sport together: Have you ever gone bobsledding? Skeleton racing? Snowshoeing? Dog sledding? Think of the most intriguing winter sports you can think of, and commit to getting out at least once to try it out and see if you enjoy it. For less expensive options, put out an ad on Craigslist to see if you can get a group together to reduce the cost.
Hit the zoo: Ever walked through the zoo when there's snow on the ground, it's eerily quiet, and some of the animals you'd normally rarely spot, shine? It can be quite a magical experience if you time it right. Zoos are usually, although not always, cheaper to visit during the winter months, but do check before heading out.
Hit the parade circuit: Maybe you decide to join the parade and create your own fun, or perhaps you're more of the lawn-chair appreciator variety of celebrant. Regardless, take in a holiday parade or two, and make bets with each other to determine who pays for dinner. Maybe the person who knows the least amount of words to the carols sung, or the person who catches less candy, but whatever it is, make it fun and and a fair competition.
Warm and Cozy
Taste test your way through town: Decide on something seasonal that you both truly love - whether it's anything pumpkin-spiced, bourbon, or candy cane -themed. Then, see how many places nearby offer taste testings, tours and/or freebies to try out, and join each other for an excursion to crown the best of the area. Alternatively, you could make it a theme for each of your dates that you'll try one thing off of this seasonal taste list, and crown your favorite on New Years Day.
Volunteer together: One of my favorite memories as a child was helping my parents deliver care baskets to families in need during several different holiday seasons. As many faiths celebrate major events during the winter months, see if yours has some form of community engagement where you and your sweetie can help others on date night.
Stay home and snuggle: C'mon. You know you want to.
Create your own top 10 lists: As a teenager, I always loved watching the top 10, or top 100 countdowns of the best (or worst) songs, videos, books and entertainment of the year. Why not spend a night together compiling your own best-of or worst-of-the-year lists, and then enjoy them together? I've got some ideas started for you with my Romantic Holiday Movies list.