My Top Winter Travel Destinations

I see winter travel as a great way to break up the monotony of a slow, dark, and sometimes boring season. I hear many people complain about the lack of sunshine and shorter daylight hours. It helps to have a trip or 2 planed to keep that “summer excitement” feeling all year. Personally, I love this time of year as the vibe is more toned down and it is a fun time of the year to cozy up with cocoa and play board games, watch movie marathons, read, and lounge around the house without feeling guilty. It’s a great time to recover and repair after the hustle and bustle of the summer season. I do a lot of physical activity during the warm months, so I actually love this opportunity to relax a little bit more.

A few years ago I took up cross country skiing and I’ve been skating for a while now, so this helps me stay motivated. I also love staying in wooded resorts and cabins this time of the year. Plus, many cities shine their brightest this time of the year with holiday events and festivals to partake in. I like to mix in city getaways with rustic getaways as both can be equally enjoyable.

Take a look at some of my favorite cold weather getaways. For each destination, I have highlighted a mix of wintry sports and holiday attractions.

Chicago, IL

Chicago is my kind of city, especially during the festive season. No city really competes with Chicago during the Christmas season. I may be biased as a native, but I really love this city over the holidays. It’s no surprise that many Christmas films are set in the Windy City. Home Alone, Christmas with the Kranks, Christmas Vacation, and Fred Claus all use Chicago as a base. With several wonderful ice rinks, the best zoo lights in the country, iconic parades and festivals, and the best Christkindlmarkt, the holiday feeling is really all around in The Windy City.

*Ice Skating at Millennium Park – The McCormick Tribune Ice Rink is open from November to March. I love that I can skate for free (on weekdays with your own skates). Someday, I would love to take the free skating lessons which are offered on weekend mornings at 9am (skate rentals extra)! I love the city views and easy access to big city attractions like the famous Cloud Gate artwork (the reflective pic above). Note it can get really crowded on weekends.

*Museums – I love The Field Museum (awesome dinosaur and mummy exhibits) and The Shedd Aquarium (best aquarium in the country). Check the websites for special holiday events including the magnificent Christmas Around the World festival at The Museum of Science of Industry. You can learn more about the Museum Campus on the city’s official page.

*Lincoln Park Zoo Lights – This colorful lights display is a real bargain at just 7-10 bucks a person (and free every Monday!). See millions of lights in a colorful display, enjoy seasonal food and drink, and marvel at ice carving demonstrations. A fantastic event which runs from late Nov-early Jan.

*Winter Holiday Events – There are plenty of holiday events such as the downtown Tree Lighting at Millennium Park, Christkindlmarket (a German holiday market where you can buy handcrafted ornaments, specialty German food, and cocoa in souvenir mugs), The Magnificent Mile Lights Festival, and more!

As a lifelong resident, I have found ways to beat the winter blues. You can take a look at my full guide to winter fun in The Windy City for some ideas to add to your bucket list.

Flagstaff, AZ

Many tourists only visit the Phoenix region to soak in the winter warmth and sunshine. Just 2 hours north of the Sonoran desert lies one of the snowiest cities in the country. Yes, that’s right. Flagstaff, a high altitude mountain paradise sits at an elevation just above 7000 feet. The mountain oasis is home to the state’s tallest mountains, the San Francisco Peaks. I lived here for several years and enjoyed the winter season the most. I basically kept myself busy every weekend skiing, snowshoeing on the mountain trails, and enjoying cozy local cafes and restaurants.

*Buffalo Park – The 2 mile loop is perfect for cross country skiing and snowshoeing after a major storm. Bonus points for the gorgeous mountain setting. You can even catch a peak of the state’s highest mountain range (The Peaks) from this trail. I often came here after a big winter storm to snowshoe. It’s just the perfect winter wonderland setting with the grand mountains in the background.

*Snowbowl – Arizona’s premier ski resort is the place to ski, snowshoe, and enjoy the wintry atmosphere. With an average snowfall of over 260 inches, the conditions are always fantastic for skiing. Snowbowl trails (the Aspen Nature Loop and Kachina) offer the perfect alternative for non skiers to enjoy the wintry setting. Bring your snowshoes and enjoy an idyllic winter walk in a gorgeous pine forest setting. I almost felt like I was in Narnia at times with the tall pines and lack of any foot traffic.

*Arizona Nordic Center – Wonderful cross country skiing destination nestled amongst the gorgeous ponderosa pine trees. Features 40 km of groomed trails with options for beginners and advanced skiers. I had a blast here, enjoying the quiet pine scenery while getting in an all over body workout.

*Ft. Tuthill – Gorgeous quiet park located in the country’s largest ponderosa pine forest. Enjoy miles of trail (along the FUTS) for cross country skiing and snowshoeing. I lived 5 min from this park and used it heavily year-round, and mostly in the winter for snowshoeing and sledding. It’s my top pick for sledding; there are lots of small hills and free parking.

*Oak Creek Canyon – Just south of Flagstaff begins the amazing Oak Creek Canyon drive, a 14 mile journey which begins near the ponderosa pines and ends near Sedona’s iconic red rock formations. This drive is super peaceful in the winter and if you are lucky, you may just catch a glimpse of the red rocks dusted with rare sow! One of my most memorable drives ever was seeing the red rocks dusted with snow; it melts fast, so you need to get out here quick.

I recommend taking a look at my guide to winter fun for some fun trails and activities to add to your bucket list.

Philadelphia

While most tourists plan a trip to Philly over the spring and summer season to explore the historic sights in Old City, “the birthplace of America,” the city really shines during the winter. In addition to touring Independence Hall and the Liberty Bell, you can add in a few festive holiday and winter activities to your itinerary. Winter is my favorite time in Philly. I lived here for a year and really enjoyed ice skating on the river, the magnificent holiday events, and the wonderful cozy local coffeehouses and restaurants.

*Winterfest – The beautiful Riverrink ice rink along the Delaware Riverfront allows you the opportunity to burn some calories in the most gorgeous setting. After your workout, you can sit by the firepit or bundle up on a rocking chair as you sip local coffee or cocoa. To date, the most beautiful rink I’ve come across.

*Macy’s show – The beautiful Macy’s in Center City (once the historic Wanamaker building) is home to the largest fully functional pipe organ. The shows are fantastic any time of the year, but even more mesmerizing during the Christmas season. Their Christmas shows are so cute and festive. Afterwards, enjoy a free walk around A Dicken’s Christmas, featuring animatronics.

*Shop Christmas Village – This German market offers all the usual gorgeous glass blown ornaments, festive food and drink, and is located in beautiful Love Park. Lots of great photo opps here including the iconic Love sign and great city views.

*Dilworth Park ice rink – Another great ice rink, this one is located in Center City nearby many great restaurants and shops. Also, there is a fun, free, and festive choreographed light show projected upon City Hall. After your skate session, you can warm up with a festive drink at Wintergarden.

I found plenty to do during the long winter season in Philly. Check out my winter guide to the best events, activities, and restaurants to enjoy this season.

Boston, MA

With a beautiful historic setting, wonderful restaurants, an ice rink located in America’s oldest public park, and many festive holiday productions, Boston is a great place to spend the holidays. With easy access to skiing, sledding, and snowshoeing right outside the city limits, it’s also a great base for winter trips. A trip to Boston allows you to enjoy the benefits of both city amenities and winter recreation.

I lived in the metro for 2 years and enjoy the variety of things to do throughout the 4 seasons. The main benefit of the winter season was the lack of tourist crowds (the downtown is so empty!), easy access to winter sports, and beautiful barren parks.

*Ice skating at Frog Pond – The Boston Common Frog Pond Rink is open Nov-March and hosts competitive figure skating events. There is a small admission free so bring your own skates (rentals are pricey). The setting is gorgeous in historic Boston Common, the country’s oldest park.

*Grab a hot drink and walk around Boston Common – There are so many local places to enjoy a hot cup of coffee or hot cocoa. One of my favorite coffeehouses near Boston Common is Thinking Cup. This was the first coffeeshop in Boston to serve the renowned NYC based Stumptown coffee.

*Make sure to be in town for the Annual Christmas tree lighting – This event is super festive with live music performances, hot drinks, and live entertainment! I have been to a lot of tree lightings, and this one is by far my favorite.

*Grab a bite to eat at Faneuil Hall Marketplace – Lots of great restaurants to take a break from your holiday shopping! Unfortunately, they closed the Cheers replica a few years ago. You can still enjoy Ned Devine’s Irish Pub, Wicked Lobsta, and more than 20 other local and chain restaurants.

*See a holiday productions – Every December, you can look forward to The Nutcracker, Holiday Pops, A Christmas Carol, and a host of festive shows.