Winter travel destinations are a little bit different. You have to factor in cold weather of course, and from there decide on what exactly you’re looking for. Are you seeking a refuge from the cold season, or a place to spend time outside? Or are you looking for a charming winter town where you can simply embrace the season? Your answers to these questions will point toward wildly different destinations. But to provide a little something for everyone, we've put together a range of different kinds of places in the list below:
1) Chester, Vermont
If you’ve ever driven through Vermont, in winter or otherwise, you may have noticed it’s full of charming little towns. Mountainous surroundings, quaint main streets, diners and cafés, and ski shops are the norm. Chester is just such a town, and while it can be cold and snowy during the winter, its charms will only intensify as a result. Additionally, the town is located not far from Killington and very close to the Okemo ski resort, which is one of the most popular ski areas in New England. There’s something to be said for Chester and the surrounding area for skiers who want good slopes and conditions during the winter but aren’t looking to travel to the Rocky Mountains and their expensive, over-the-top resorts. This is more of a laid back, outdoors-y area that happens to have good skiing.
2) Scottsdale, Arizona
If you want to escape the cold but you don’t want to go full-on tropical, Arizona can be a good place to look. The area isn’t quite as toasty as you might expect given its reputation for sun and deserts, but much of the state still avoids the worst of winter. Scottsdale is also a nice, simple city with a charming Old Town and some modern attractions, but also a perfect place for those who want to do some hiking or perhaps nearby camping. In short, from nearby trails, to a wildlife conservation center, to gardens and campgrounds, there’s a lot of outdoor activity you can enjoy even during the colder months.
3) Boulder, Colorado
Boulder is one of the prettiest cities in the United States, and a nice little winter wonderland once the weather cools off. The city is known for its comforts - breweries, warm pubs, excellent restaurants, etc. - but there are also trails into the hills around the city that are accessible even during the winter if you want a more rugged stay. Boulder is also a nice base for a few other activities around Colorado. It’s not very far to Denver, where you can get more of a city experience and maybe even see some winter sports. The NBA’s Nuggets have a famously fun home atmosphere, and the Denver Broncos are just a few years removed from a Super Bowl appearance, and still a fun franchise. You can also find skiing experiences from Boulder, with Breckenridge and the Arapahoe Basin being the closest options.
4) Saint Augustine Beach, Florida
If you just want to go somewhere legitimately warm and spend some time outside - laying on the beach or just sitting outside your accommodations enjoying the weather - Saint Augustine Beach is a great option. This is an area I’m pointing to because despite being on Florida’s Atlantic Coast and in line with other more famous attractions, it’s not known for attracting quite as much of a crowd as, say, the Palm Beach or Tampa areas. And you’re still close to other places if you’d like to take a day trip for a bit more activity. Most notably, Orlando and its incredible array of things to do is just a short drive away, meaning you can easily make this vacation a combination of relaxation and activity.
5) Jackson, Wyoming
If you want to fully embrace the winter season and see one of the most beautiful parts of the country, Jackson, Wyoming is the place to go. Somehow, more than other winter destinations and ski areas, Jackson seems to maintain a laid-back country atmosphere despite being a wealthy area and a tourist draw. That makes it a treat just to relax there even if you don’t venture out to the nearby ski slopes.