9 Festive Winter Activities

Contrary to most, wintertime is one of my favorite times of the year. I love cold brisk temps, snow, hot cocoa, ice skating, cross country skiing, cozying up on the couch and watching holiday movies, and most of all, festive events. With the holidays just around the corner, now is the time to start making your plans for fun, festive events and activities in your area.

To help get you into the holiday spirit, I have compiled a list of a few wonderful winter and holiday happenings and activities around the country. I have personally attended all these events and can say that they are worth traveling for.

Update: I have visited some of these destination again recently. You will find some updated photos, info, and pricing info. Enjoy!

1. Strolling around Chicago’s Lincoln Park Zoo Lights

Chicago’s Lincoln Park Zoo offers an amazing holiday lights spectacular each year. I have been to several zoo light shows, although none have come close to the grandeur of this display. Featuring hand carved ice carving demos, over 2 million multi colored lights, synchronized music shows, & ongoing special events throughout the season, this event is a must-see by anyone who loves looking at beautiful Christmas lights.

Update: This event keeps getting bigger. As of 2025, there are now 3 million lights. It’s a small space, so this is a jam packed display of holiday cheer!

Enjoy walking around a winter wonderland while sipping spiced wine, enjoying a rich hot chocolate, or splurging on a new holiday treat. The display runs from late November to early January.

Best of all, admission is just 7-12 bucks (and free on Mondays!). This is way cheaper than the $20-30 most zoos charge, so take advantage during your holiday trip! Trust me – it’s great. I am a Chicago native and I try to return to this fabulous event anytime I travel back home!

Check the zoo website for details involving this year’s operating dates & special events.

Check out more of my favorite things to do in The Windy City over the freezing winter season. You would be surprised at just how much there is to do with all the wonderful museums and holiday attractions in and around the city.

2. Touring A Christmas Story House and Museum in Cleveland, Ohio

Did you know that the house from the classic holiday film, “A Christmas Story” is now used for public tours? I just found out myself on my first trip to Cleveland.  In the historic Tremont neighborhood, you will find Ralphie’s house from the movie (leg lamp in the window and all) open to the public year-round. I loved taking my pic next to the famous lamp, as well as Ralphie’s Red Ryder!

You will have the unique opportunity to freely roam through the house, which was restored to match the exact set up featured in the film. Our tour guide provided plenty of interesting tidbits regarding the actors and filming process. The gift shop contains a wonderful assortment of novelty gifts, which make shopping for fans an easy task. I also loved the collection of Christmas Vacation (one of my favorites for sure) and Elf souvenirs.

The museum is stocked with memorabilia from the movie (movie stills, scripts, actor’s clothing items, actual props, and more!). We attended the 30th anniversary celebration (wow, don’t you feel old now?!). Visit the house website for details regarding admission prices and hours. Also, you can rent out the actual house or the neighboring Bumpus house. How cool is that? It’s going to cost you, but may be worth depending on just how big of a fan you are of the film.

Update: In 2025, this film will be celebrating its’ 42nd anniversary. I feel even older now 🙁

3. Ice Skating at Chicago’s Millennium Park

What better way to warm up on those blustering cold Chicago days than skating to holiday music, surrounded by amazing architecture? I love this downtown, especially when all the holiday festivities are going on. There is no better big city to spend Christmas in. I grew up in the city and loved visiting downtown at least once during the holiday season to see the spectacular Macy’s Windows (then Marshall Fields) and the grand tree at Daley Plaza.

Being surrounded by skyscrapers in one of the country’s best downtown areas just adds to the excitement. This festive activity also doubles as an awesome workout (one that you will actually enjoy!).

Don’t forget to get your pic next to the famous Cloud Gate Sculpture (aka “the Bean” to us locals)

Each Friday during the month of December, you will have the opportunity to listen to carolers from various local choral groups. When you are done skating, you have your choice amongst dozens of restaurants and coffee shops to warm up.

The rink typically opens for the season mid-late November and stays open through March. Ice skating is free if you have your own skates on weekdays, however, skate rentals are $17-20 if you do not own a pair. Free skating lessons are offered Sat & Sun mornings at 9am (register online). I would love to take lessons some time as I am not very good. That being said, I do try to get out at least a few times each season. Visit the Millennium Park Website for details regarding this season’s operating dates and special events.

While you are in the vicinity, definitely check out Chistrindlmakret, one of the oldest and best European Christmas markets in the US. They serve cocoa in the cutest souvenir mugs and you can also feast on all sorts of German and Polish foods like potato pancakes and pierogies.

4. Shopping, Dining, Skiing, & Skating at Lake Tahoe’s Squaw Valley

Squaw Valley (update: now Palisades), home to the 1960 Winter Olympics, is one of the largest ski resorts in the US. The highlight here is a scenic tram ride, which takes you on a 2000 foot adventure high above the spectacular mountains of the Lake Tahoe region.

At an elevation of 8200 feet, you will be treated to really amazing views you won’t find anywhere else. You can take some nice photos up here. I think this area is one of the most gorgeous vacation destinations anywhere in the US. I was so lucky to live in Nevada for a while where I could hop quickly over for the weekend.

Winter activities include: ice skating, snow shoeing, cross country skiing, and dog sledding. It’s nice you don’t have to be a skier to enjoy the beautiful scenery surrounding Tahoe. I like hiking at Emerald State Park, but skating alongside the mountain scenery is really memorable too.

Also, there is a nice tribute to the Olympics for those interested in sports. I had fun taking my pics by the podium and rings.

At The Village, you will have your pick amongst an assortment of restaurants and shops. Outdoor fire pits, holiday decor, and snow capped mountains add to the festive setting. It’s a great time of the year to browse around and enjoy a special dinner. We stopped at a nice little wine bar called Reserve one time when someone gave us a free tasting (it was great!). Most of all, I really love just walking around taking in the scenery I can’t see at home. There is nothing like walking around a snowy mountain town to get into the holiday spirit.

You can check out my Tahoe vacation guide for more details on the best things to do.

5. Ice skating in Boston Common

The highlight of the winter season in Beantown is ice skating in beautiful Boston Common. I love this park during the summer months, but I also love ice skating. In the winter, Frog Pond is transformed into a festive ice rink, surrounded by beautiful lit up trees. The ambiance is so festive and they even put on free skating shows a few times per year.

After working up a sweat, I recommend a stroll around historic Boston Common, the country’s oldest public park. This is also where you will find the annual Christmas tree. Like Chicago, I prefer the city during the quiet, quaint winter months. The lack of tourist traffic, beautiful brisk temps, and high likelihood of snow transform the city into a festive wonderland this time of year.

I love skating at Frog Pond. I skated here at least a times each few winter season after relocating to the area. Yes, it is a hassle to get downtown and parking can be pricey, but it is worth it for the fantastic setting in beautiful Boston Common. The rink typically opens in late November and closes in March. Visit the Frog Pond website for information regarding operating hours and prices.

One of the things I love most about this city is that it’s so easy to find free things to do. I wrote a guide highlighting my favorite free city attractions (after living in the metro for several years) for anyone sticking to a budget.