Fun & Beautiful Winter Destinations

Although many associate the winter season with endless snow shoveling and frigid temperatures, this is also a great time of the year to participate in fun sports and enjoy seasonal festivities. Instead of thinking of snow as a burden, I recommend enjoying it. Personally, I love snowshoeing, cross country skiing, and ice skating. I can’t wait to get out there after a big storm and enjoy it all.

In this guide, I will cover a few of my favorite winter getaways. After living in or near of each of these regions, I can say that the cold weather season is never boring if you are prepared and have events to get excited about. I have highlighted urban areas which offer bustling ice rinks and holiday events, and also cozy, hidden gems, far away from any civilization. One thing’s for sure – each area offers its’ own unique attractions, activities, and above all, a beautiful, festive setting to enjoy this beautiful time of year.

Update: Since writing this post a long time ago, I would add Flagstaff (a dream winter destination in Northern Arizona), Philadelphia (so many great holiday festivities), and even Pittsburgh (home to so many wonderful ice rinks & museums) to the lineup. Also, note that I have updated some pics and content to reflect more recent visits.

1. The White Mountains of New Hampshire

The White Mountains, part of the northern range of the Appalachians, is the perfect getaway for city dwellers who are craving some much needed peace and quiet. The region is a popular year-round vacation destination due to its’ close proximity to cities like Boston and New York. I took several vacations here while living in the Providence, RI metro and really enjoy the winter season amenities and scenery.

There are so many quaint towns and villages which offer an idyllic setting for winter and holiday vacations. Most towns in the mountains get plenty of snow, opening the door for endless seasonal fun. I really love the quaint nature of Jackson. It’s such a charming small town and one of my favorite attractions is located here.

Jackson

Jackson is a tiny town (population just over 800) in the White Mountains region. It is a very popular vacation destination due its’ proximity to ski resorts, and secluded location. The beautiful covered bridge as you enter the town is a wonderful photo opportunity. These beautiful reminders of the past are vanishing each year, so definitely check them out whenever you get the opportunity. Who knows how much longer until they are all gone?

Top activities in Jackson

Visiting Nestlenook Farms is like taking a walk through a holiday snowglobe. At this snowy 65 acre resort, you will have the opportunity to take a horse drawn carriage ride around the beautiful property, which is surrounded by incredible views of the White Mountains. Wrap yourself in a blanket, grab a hot cocoa, and enjoy the snowy mountain views. This is one of my most memorable holiday experiences to date.

After your sleigh ride, grab your skates and head over to the 3 acre Victorian Ice Rink for a wonderful afternoon of skating alongside snow capped mountains. Old fashioned chime music and views of the Austrian sleigh passing over the bridge create an incomparable setting. After your session, take a break with a warm cup of cocoa by the fireplace in the warming hut. I really loved the isolated nature of this rink, plus the incredible mountain scenery. It was a bit scary skating with nothing to hold on to, but I didn’t fall!

With beautiful mountain views, charming architecture, and the sights and sounds of nature all around you, this small mountain town is the ideal place to embark upon a skiing adventure. Jackson Ski Touring Foundation offers rentals and lessons for beginners. I skied at gorgeous Bretton Woods which offers a variety of train for all levels. The snowy pine backdrop is too amazing to put into words.

Bretton Woods is the largest ski area in New Hampshire, with 62 trails and 3 terrain parks. They also offer night skiing, so you can continue on as long as you like. You can read more about my experience skiing here for more details.

2. Chicago, Illinois

Although Chicago is a popular tourist destination during the summer months due to the beautiful lakefront path, wonderful museums,  and wonderful architecture, there is no shortage of winter fun in store. I think Chicago is easily the best urban city to spend the holidays in and I am not just saying that as a native. If you can brave the chilly temps, you will have the opportunity to enjoy the many wonderful seasonal events and activities in and around the city.

Top activities in Chicago

Every winter, Millennium Park is transformed into a winter wonderland with the annual opening of the McCormick Tribune Ice rink in front of the famous Cloud Gate Sculpture (aka the bean to locals). As you test out your skating skills, you will be treated to views of some of the finest architecture in city. It’s my favorite rink anywhere – you can’t beat the beautiful cityscape views. Plus, you can easily walk to the Christmas tree and other holiday attractions from here.

A holiday season in The Windy City would not be complete without walking along the Magnificent Mile. On this famous street, you can shop and dine a wide range of luxury and mid end shops. There are too many great restaurants to list, but if you like pizza, definitely try the deep dish at Gino’s East. I also love the lasagna at Lou Malnati’s. The season kicks off early in November with the annual Magnificent Mile Light Festival, featuring a parade, live performances, and a special fireworks show.

Brookfield Zoo, located in the Chicago suburbs, offers one of the best holiday extravaganzas in the area. Along with taking in the sights of over 1 million LED lights, you will also be able to watch live ice carving demonstrations, listen to carolers, enjoy hot treats, take a special holiday tram ride, and visit indoor exhibits.

Lincoln Park Zoo is another great zoo, this one is located not too far from downtown. It is much smaller than Brookfield, but offers a fantastic holiday light display (better than Brookfield, in my opinion). The annual Zoo Lights festival is truly one of a kind. Grab a spiced wine or hot cocoa and enjoy strolling around while taking in the colorful display. I love the setup here – not a single tree is left undecorated. You will also find an amazing synchronized light show, ice carvings, and ice skating on the lineup. Best of all, admission will only set you back 5 bucks!

Christkindlmarket is one of the city’s most popular annual events, with guests coming from around the world. Here you will find many vendors, including several offering the most beautiful German ornaments, along with a selection of German food and drinks. I love the Käthe-Wohlfahrt collection. Also, try the potato pancakes and pierogies!

One of my favorite holiday activities is seeing the iconic State Street windows. Be sure to make reservations (a waiting list opens in late Sept) for lunch at The Walnut Room, located on the 7th floor of Macy’s, for a holiday lunch next to the grand 45 foot tall tree (it’s so gorgeous!). Try the Franco Mint cheesecake for a real treat!

3. Lake Tahoe

Lake Tahoe is a year-round recreational playground. Fom cruises and spectacular hikes (I love Emerald Bay State Park) in the summer months, to world class skiing and festive ice skating in the winter months, there is never a dull moment. Skiing draws in most tourists, but as a non skier I have found plenty to do.

I’ve visited both summer and winter multiple times and actually prefer the wintertime. With seasonal sleigh rides, ice skating, snowshoeing, and seasonal shows at the Stateline casinos, you won’t miss skiing one bit.

Top activities in Lake Tahoe

Squaw Valley, home to the 1960 Winter Olympics, is the area’s top ski resorts. This North Lake Tahoe resort is home to 42 lifts, 270 trails, and a very long ski season due to the abundance of yearly snow (450 inches on average!). There is a really cool museum at the top where you can browse some cool memorabilia.

After your day on the slopes, check out The Shops at Squaw Valley, a scenic mountain side shopping, dining & entertainment village. Cozy up at the outdoor firepits with a warm drink as you take in the beautiful holiday decor of this quaint shopping destination.

Non skiers can enjoy a scenic aerial tram ride up 2000 feet to base camp, where you can enjoy a host of activities including skating on a gorgeous mountainside ice rink. I really loved the views on the gondola as well as exploring the Olympic memorial. Other options for winter fun include: tubing, snowshoeing and cross country skiing on the resort’s trails, and taking a guided dog sled tour. Update: Squaw Valley is now Palisades. For a full activity guide check out the resort’s website.

Heavenly Mountain Resort, conveniently located within walking distance from the casino resorts, is another great skiing and entertainment destination. Skiers will enjoy the variety of terrain, while non-skiers can enjoy the abundance of other winter activities (ice skating, tubing, and sleigh rides). I really loved this charming ice rink. Afterwards, we enjoyed walking around the shops which including a lot of mountain good stores and novelty shops. We also enjoyed a rare treat at Coldstone. More info and a shopping directory on the Heavenly website.

4. Southern Idaho

Wintertime in Southern Idaho is the perfect opportunity to take a step back and enjoy the beautiful parks in a quieter setting. Although the ski resorts are nowhere near as spectacular as those found in more popular nearby destinations like Jackson Hole, rates are cheaper and crowds are pretty much non existent. Skiing, snowboarding, snowshoeing, tubing, and ice fishing are a few of the most popular pastimes amongst locals and visitors. 

Top activities in Southern Idaho

Harriman State Park is a great choice for anyone seeking an affordable way to enjoy the outdoors. Trails vary from beginner to advanced and rates are affordable to enjoy the groomed trails. This was my first experience cross country skiing and I really enjoyed it even though some of the hills were tough to climb up and scary to go down.

Craters of the Moon National Monument transforms into a playground as soon as the snow begins to fall. The park maintains a 1.5 mile snowshoeing trail and several miles of cross country skiing trails during the season. During January and February, the preserve hosts free weekend guided snowshoe journeys which is a great program for beginners. During the winter season, entrance to this magnificent historical sight is free, so be sure to take advantage.

Kelly Canyon ski resort, located 30 miles north of Idaho Falls, offers beginner through advanced trails. It’s very popular with locals due to the convenient access and attractive night skiing option (most ski runs are open until 9:30pm).

Soon after moving here, locals were telling us about this awesome hot springs. What better way to warm up on a cold night than a visit to a relaxing hot springs? These natural mineral enriched springs (temps range from 102-112), contain beneficial minerals like potassium, calcium, and magnesium. No chemicals are used, so there is no worry about absorbing unwanted elements.

5. Providence, Rhode Island

Providence, the capital of Rhode Island and one of America’s oldest cities, has much to offer during the winter season. Although the area is lacking in ski resorts, you will find an assortment of great cultural events and activities to partake in all season long. Here’s a brief overview of some of my recommended attractions.

Top activities in Providence

Each season a rink double the size of Rockefeller opens in the heart of downtown. This amazing rink is beautifully decorated, always playing festive music, and surrounded by gorgeous views of the city skyline. Special live performances throughout the season add to the excitement. I highly recommend choosing this rink over Boston as the setting is much nicer and it’s easier to find affordable parking.

At the end of November each year, the fantastic Roger Williams Park Zoo holds an annual holiday celebration, complete with a festive parade and visits from Santa.

Many area parks & trails such as the Blackstone Blvd. Walking Path (Providence) and Lincoln Woods offer flat trails and roads for cross country skiing and snowshoeing. If you are willing to drive a bit, I recommend Myles Standish, my favorite recreational area in the state.

And of course, you can’t visit the historic Federal Hill neighborhood without enjoying some authentic Italian cuisine. I recommend Andino’s for their awesome shrimp scampi.

 6. Bozeman, Montana

Bozeman, most well-known for being home to Montana State University, is a small, friendly Western town to consider for a laid-back winter vacation. If winter sports are your thing, then you are in luck as Bozeman gets a lot of snow each season due to its’ high altitude.

Various snowshoe and cross country ski trails will keep you busy during your trip. If you prefer downhill skiing, you have plenty of options both in and around the city. Bridger Bowl offers 75 trails ranging from beginner to advanced.

A day trip to Yellowstone is another great option as the wonderful national park lies a mere 2 hours away from the entrance. Guided snowmobile and snow coach tours are a few of your options for seeing the park during the snowy, closed to public vehicles winter season.

7. The Smoky Mountains

With so many wonderful year-round activities, beautiful cabin rentals, and convenient access from many major metro areas, I am not surprised that this is one of the most visited national parks. From summertime hikes to skiing at Ober Gatlinburg, the Smokies area is an ideal place to plan a getaway, no matter the season. Here’s a look at some of the fun events and activities I recommend incorporating into your plans.

Top activities in the Smokies

Timber Tops offers hundreds of luxury cabin rentals within the Smoky Mountain National Forest. Each is loaded with fantastic amenities, such as: outdoor hot tubs, fireplaces, indoor pools, and game rooms. Many offer a secluded setting and panoramic views of the mountains and/or city of Gatlinburg. A rustic cabin in the woods is the way to go in my opinion. We enjoyed our rental with Life’s a Bear, a cozy 1 bedroom featuring amazing views, a game room, an a deckside hot tub overlooking the mountains.

Ober Gatlinburg is Tennessee’s only ski resort. 9 trails are available, including an option for beginners. Skiing not your style? Check out the massive year-round ice rink or the seasonal snow tubing hills. You will also find a tram ride which takes you over the mountains. Not the most scenic in my opinion, but a worthy add on activity especially if you purchase the package deal which includes ice skating.

There are endless trails available within the Great Smokies. Laurel Falls pictured here is a wonderful paved 1.5 mile trail to a 60 foot waterfall. It’s one of my most recommended easy waterfall hikes for first time visitors. If you are up for a brisk walk, it’s definitely a must-see. Fortunately, the path is paved so a great winter choice.

The Incredible Christmas Place is the largest Christmas store in the South, and one of the most beautiful I have ever set foot upon. Simply walking through the store is an experience in itself, with over 50 beautiful trees decorated for the holidays, Singing Santa performances, and gorgeous miniature holiday village displays.

A half marathon like no other, the Santa Hustle Half Marathon series is a must for any runner who also happens to love Christmas as much as running! This festive themed race travels through the town of Pigeon Forge and ends at the Wilderness at the Smokies Resort.

Cookie stations along the way, holiday decor, an adorable holiday themed race shirt, and catchy holiday tunes to motivate you along place this spirited race high above the rest! This is one of my favorite races I’ve ever participated in – I even PR’d in this one!

Gatlinburg, your best base for exploring the Smokies, offers no shortage of festive shows. The Smoky Mountain Opry offers a special annual Christmas at the Smoky Mountain Opry spectacular, a big budget production filled with the usual top notch singers and performers, along with the added bonus of all the wonders of the season.

Each year downtown Gatlinburg comes alive with over a million sparkling LED lights. We took a festive trolley ride and the guide was hilarious. Also, you can find a self guided tour map at the visitor center and check out the lights at your own leisure.

Each year Dollywood, a large Tennessee theme park owned by Dolly Parton, hosts a special Smoky Mountain Christmas event. This festive event, which has been the recipient of many awards, features millions of lights, special holiday performances, and a holiday parade.

8. West Dover, Vermont

West Dover, Vermont, a tiny town in Southern Vermont, is home to Mt. Snow Ski Resort. The town is most famous for being the hometown of 2 Gold medalists, Devin Logan (won a silver medal at the 2014 Olympic Games in Women’s Freestyle Skiing) and Kelly Clark (won the gold medal in Women’s Snowboarding at the 2002 Olympic Games).

A trip to West Dover is an ideal quick weekend ski option for those traveling from many large cities in New England. We enjoyed a quick weekend escape here from the Providence metro. It’s a great place to escape the city congestion for some fun in the snow.

Activities at Mt. Snow Ski resort include: skiing, snowshoeing, dog sled tours, sleigh rides, snowmobile tours, and cross country skiing. I recommend staying at a rustic little B & B called Kitzhof Inn. This property is attractively decorated with a nice common room with a cozy fireplace and bring your own beer/wine bar. You can take a free shuttle to the ski resort too which is nice.

9. Boston, Massachusetts

Although the thought of spending the holidays in a busy city may seem unattractive, Boston surprisingly offers a more laid-back setting than many other major metro areas this time of year. Most tourists tend to skip winter visits in favor of the warmer summer months and college students are on holiday break, leading to a much more peaceful downtown ambiance.

When I lived here, I actually prefer the peace and quiet of the winter season. I actually preferred exploring major sights like The Freedom Trail without the sun beating down on me and hoards of crowds all trying to take the same pictures.

There are a lot of fun winter activities to make your trip more exciting. If you tire of the cold, you can always take a break at one of the city’s highly regarded cultural attractions (New England Aquarium, Museum of Fine Arts). Below are a few activities and attractions I recommend adding to your bucket list.

Top activities in and near Boston

Frog Pond in historic Boston Common is transformed into a beautiful ice rink each winter season. Skating while enjoying the stunning old architecture, all while taking in the holiday lights, is a truly memorable experience.

The Zoo’s annual festival of lights includes sparkling light displays, visits from Santa, and reindeer photo opportunities. Stoneham is located a mere 20 minutes from the city, enabling both locals and tourists to take part in the festivities.

Cross country skiing and snowshoeing are available on both the 9 miles of natural trails and the 1.5 miles of snowmaking trails. In addition, the trails are lit at night for those who can’t make it out there during the day. Skiing and snowshoeing lessons are available.

Blue Hills Ski Resort, located just 20 minutes from the city in charming Milton, Blue Hills offers 90% snowmaking on its trails (there are 12 total). Highlights at this local resort include night skiing and special promotions throughout the season. Blue Hills is a great alternative for those who can’t make it all the way up to the bigger resorts in Vermont every single weekend.

The Nutcracker, a timeless classic, returns every winter season to the Boston Opera House. Nothing starts the winter season quite like seeing a festive live production of The Nutcracker. After your show, there are plenty of fantastic restaurants to check out.

Boston’s Annual tree lighting ceremony kicks off the holiday season each year with a festive lineup, including: the lighting of the grand tree (an annual gift from Nova Scotia as a thanks for the emergency help provided in the Halifax explosion of 1917) and smaller trees around Boston Common, special celebrity live performances, and visits by Santa. I love that the tree is walkable from the ice rink so you can combine a few holiday activities together.

And, of course, this is the best time of the year to explore The Freedom Trail in peace.

10. Yellowstone National Park

The off season in Yellowstone offers visitors the opportunity to experience the park in a whole new setting. Although bears will be hibernating, you will have the chance to spot many diverse forms of wildlife including wolves and bison. Winter is one of the best times for wildlife sightings as the park is much quieter, and thus, animals are more likely to be out.

Only a handful of hotels operate during the winter season (Old Faithful Snow Lodge is one option), however, there are plenty of choices in the nearby towns of West Yellowstone, Rexburg, and Idaho Falls. Here’s a look at some of your best options for winter fun in Yellowstone. Note that vehicles are not permitted in the park at this time – only snowcoaches and snowmobiles.

Top activities in Yellowstone

The majority of the park’s roads close to vehicles during the winter season (typically beginning in November). Unplowed roads are open to cross country skiers and snowshoers. This is a great opportunity to explore the park in a pristine, snowy setting, and provides ample opportunities for wildlife sightings. Several area companies, including Yellowstone Expeditions, offer cross country and snowshoe tours.

Snowcoach Yellowstone offers Old Faithful and Grand Caynon of Yellowstone tours during the winter season. As you sit back and relax in a luxury snowcoach, a narrator will point out all the magnificent sights. Taking a snowcoach tour gives you the opportunity to see the park in a way that is normally closed to the public.

Several guided snowmobile tours are available from Old Faithful and the Grand Canyon of Yellowstone. Bison, elk, and wolves may be spotted along the way. Also, it is the most scenic time of the year with snowy mountains, frozen waterfalls, and beautiful canyons.

West Yellowstone is an adventure seekers paradise during the winter months. You will likely see more people out skiing and snowshoeing than driving cars. Rendezvous Ski Trails offers 21+ miles of groomed trails through pristine pine forests.

You can find more about winter activities in the park on the NPS website.

11. Newport, Rhode Island

With a beautiful coastline, gorgeous old architecture, and a charming downtown, Newport is easily one of Rhode Island’s finest cities. Most of the attractions found here can be enjoyed year round, although there is that extra something special in the air during the winter season. Check out a few of my recommend winter activities to incorporate into your plans.

Top activities in Newport

Jane Pickens, a beautiful historic theater in downtown Newport, screens a different holiday classic each year. The setting is classic and romantic. I loved seeing White Christmas, one of my all time favorites on the big screen the way it was meant to be seen.

One of Newport’s beautiful historical mansions, Rosecliff, offers a special annual performance of The Nutcracker each year. This is a wonderful experience for anyone visiting the area during the holiday season.

If you like skating, there is an ice rink in the middle of downtown, within walking distance to great shops and restaurants. It’s larger than NYC’s Rockefeller Center ice rink and offers fantastic views of the city’s charming architecture. Also, this city is home to the best restaurants. If you love seafood, I recommend indulging in some fresh lobster at The Lobster Bar. If you love Italian, there is no better choice than Mamma Luisa’s.

12. Jackson Hole

Jackson Hole is an absolute dream during the winter season. I was fortunate enough to take many daytrips here while living in nearby Idaho Falls. You have beautiful snowy mountain ranges, plenty of winter recreation, gorgeous resorts and cabin rentals, and great seasonal attractions.

Even if you are not a skier, there are plenty of other wintry attractions to take advantage. I recommend taking a sleigh ride at the beautiful National Elk Refuge, home to the largest elk herd in the world.

Top activities in Jackson Hole

The National Elk Refuge provides a winter habitat for elk and other endangered species. Each winter season, thousands of elk migrate down for the food supply. The refuge offers sleigh rides (wagon rides in the absence of snow) to take visitors around the picturesque refuge.

I loved the gorgeous mountain scenery and opportunity to see these beautiful animals up close in their natural habitat. This is a great option for non skiers to enjoy the scenery during this festive and snowy time of the year.

Jackson Hole is a winter wonderland as the region sees hefty snow all season long. Skiing, snowboarding, snowshoeing, and scenic aerial tram rides are available at the highly regarded Jackson Hole Mountain resort.

2 great snow tubing parks provide the ideal alternative for non skier. Grand Targhee and Snow King Ski area provide hours of safe, wintry fun for families.

Teton Pines Cross Country skiing provides tours at the base of the Teton Mountain Range in Jackson Hole. Both group and private lessons can be arranged. The trails are ideal for beginners as there are no steep hills. Both beginners and advanced skiers will appreciate the majestic views along the way.

The city’s quaint downtown area is the perfect place to stroll around on a wintry day. It’s like taking a step back in time to the old west. You have local restaurants, shops, and a beautiful mountain backdrop. Pictured below is one of the elk antler arches. There are 4 of these which are comprised of the antlers shed (naturally) by the elk from the refuge. You will learn more about how and why elk shed their antlers if you take the sleigh ride at the refuge.

 13. Southcoast Massachusetts & Cape Cod

The South Coast of Massachusetts typically refers to the towns found in Plymouth and Bristol counties. This area includes the Fall River and Plymouth metro areas. Although the area is home to many dense urban areas, there are plenty of pockets of beautiful natural recreation.

Myles Standish is the biggest recreation acre in Southeast Massachusetts. It also happens to be one of the most beautiful and secluded parks in the area. Conveniently located just a short drive from Plymouth, this year-round wonder provides hours of entertainment for locals and tourists.

After a big snowstorm, I recommend heading over to the park’s trails for miles and miles of snowshoeing and/or cross country skiing. The setting is so quiet and wonderful. This was my favorite year-round nature oasis as a local for many years.

La Salette Shrine in Attleboro offers an amazing, free holiday light show, complete with almost a million lights and a must-see synchronized show. This event has been going strong for over 60 years! I was really impressed with this display, and more so the beautiful tranquil ambiance.

Christmas on the Cape is a monthly festival of everything Christmas (parades, light festivals, holiday promotions, and more) in various towns throughout Barnstable County. Each town on The Cape puts forth its’ own unique decorations and traditions, many of them capturing the magic of Christmas of the past.

As you stroll around the various old-fashioned downtowns, you can treat yourself to a holiday shopping experience at unique, local businesses as opposed to stuffy, overcrowded malls. Special events include: the Hyannis holiday stroll, Holiday on Cape Cod by the Cape Symphony, and the lighting of the Provincetown monument.

A special holiday themed ride on the Cape Cod Central Railroad in Hyannis includes a visit by Santa, cookies and hot chocolate, and Christmas carols.