A Travel Price Comparison for United States of America Winston-Salem vs. Aspen for Food, Nightlife, Couples, and Families

Should you visit Winston-Salem or Aspen?

Which is cheaper to visit? Which is more expensive for vacation?

Should I visit Winston-Salem or Aspen? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Winston-Salem

Winston-Salem is a friendly, under-rated, and welcoming city. Other popular activities here include shopping, museums, and nightlife. See Winston-Salem travel costs.

Aspen

Aspen is a quaint, vibrant, and artsy ski town. This is a great small town that is just waiting to be explored. With stunning beauty, Aspen attracts visitors from all around. As this is a very quaint destination, you'll find it has a special atmosphere. Other popular activities here include live music, food, and hiking. See Aspen travel costs.

Winston-Salem and Aspen: Pros and Cons

Pros
  • Popular museums and historical sights
  • Active nightlife
  • Scenic old town
  • Family-friendly
  • Good for students
Things to Consider
  • Less popular for food
  • Less popular with couples
  • Less walkable
Pros
  • Popular for skiing
  • Popular for food and cuisine
  • Active nightlife
  • Good music scene
  • Nice resorts
  • Good for hiking
  • Popular at Christmas
  • Known for Christmas markets
  • Known for its beauty
  • Family-friendly
  • Good for couples and romance
  • Very walkable
  • Small town charm
  • Impressive beauty


Is there more to do in Winston-Salem or Aspen?

Travelers will usually find more to do in Aspen. Although Winston-Salem and Aspen are popular destinations, Aspen has more sights and attractions for tourists. Aspen is very popular for its skiing, food, nightlife, music, resorts, hiking, shopping, christmas markets, small town charm, impressive beauty, and quaint atmosphere, while Winston-Salem attracts visitors for its museums and attractions and historical sights. Aspen is more touristy than Winston-Salem and is known for its world-class skiing, many food, film, and music festivals, and its stunning mountain hikes. It is also well known for The Maroon Bells. Winston-Salem is famous for it's southern character and quaint college campuses.

How is Winston-Salem different from Aspen?

Which is Better for a Holiday?

Let's take a look at the differences and similarities between Aspen and Winston-Salem. Then, you can decide for yourself which place is better for your next trip.

Is Winston-Salem or Aspen Better for Skiing?

Winston-Salem
Aspen

Aspen is renowned for snow skiing. However, Winston-Salem is not a skiing destination.

If you're an avid snow skiier, Aspen should be on your list. Near the town, there are 4 separate ski resorts. In town you'll find Aspen Mountain, which is known for it's black-diamond runs. Aspen Highlands, a couple miles away, has a mix of slopes and is less crowded. Buttermilk attracts many freestyle skiers and Aspen Snowmass is considered one of the best family-friendly ski areas.

Winston-Salem is not a skiing destination.


Are the Museums and Historical Sights Better in Winston-Salem or Aspen?

Winston-Salem
Aspen

Winston-Salem is a city with good options for its museums and landmarks. However, Aspen does not have museums and landmarks.

If you're looking for an educational opportunity, there are a decent number of museums and historical sights around Winston-Salem. Old Salem has a nice concentration of museums and gardens. Outside of the old town you'll find several art museums like the Museum of Early Southern Decorative Arts and the Reynolda House Museum of American Art.

Aspen does not have museums and landmarks.

Is the Food Better in Winston-Salem or Aspen? Which Destination has the Best Restaurants?

Winston-Salem
Aspen

Aspen is renowned for its local cuisine and restaurants. Also, Winston-Salem is not as famous, but is still a good city to visit for its restaurants.

For foodies, Aspen is an obvious choice, as it is one of the food capitals of the world. The town hosts many food festivals and there is a growing selection of diverse restaurants. In town you'll find cafes and restaurants that cater to both the local crowd and the travelers who flock to the area during peak seasons.

There are plenty of up and coming restaurants around Winston-Salem. North Carolina barbecue is popular around town. The city is also the birthplace of Krispy Kreme donuts and during the holiday season you should sample the local Moravian Cookies.

Is Winston-Salem or Aspen Better for Nightlife?

Winston-Salem
Aspen

Aspen is notable for its evening party scene. Also, Winston-Salem is not as famous, but is still a good city to visit for nightlife.

Aspen has plenty to do after the sun goes down. The people in Aspen know how to have a good time. The nightlife scene includes craft beer, live music, and dancing. There's a local vibe, particularly during the off-season times when the tourist crowds are less.

With a handful of venues, visitors can find a fairly lively vibe in Winston-Salem. Local breweries are popping up around town. You'll also find active nightlife venues near the colleges and universities.


Is Winston-Salem or Aspen Better for Music?

Winston-Salem
Aspen

Aspen is notable for its music scene. However, Winston-Salem is not a live music destination.

If you love music, you'll find something to enjoy in Aspen. Popular music venues in town include Silver City Mountain Saloon and Belly Up Aspen.

Winston-Salem is not a live music destination.

Is Winston-Salem or Aspen Better for Resorts?

Winston-Salem
Aspen

Aspen is notable for its resorts. However, Winston-Salem is not a resort destination.

Aspen is known as a popular and fun resort destination. Popular resorts in the area include The Little Nell, Hotel Jerome, and St. Regis Aspen.

Winston-Salem is not a resort destination.

Is Winston-Salem or Aspen Better for its Old Town?

Winston-Salem
Aspen

Winston-Salem is a city with good options for its historic old town charm. However, Aspen does not have a historic old town.

Winston-Salem offers a nice historic old town area. Nearby Old Salem is filled with historic museums, gardens, and restaurants. A ticket is required for most of the venues, but the atmosphere and architecture are charming.

Aspen does not have a historic old town.


Is Winston-Salem or Aspen Better for Hiking?

Winston-Salem
Aspen

Aspen is notable for the nearby hiking options. However, Winston-Salem is not a hiking destination.

Aspen is a popular spot for hiking. During the summer and fall seasons, hiking is a great way to explore Aspen's nearby beauty. Popular trails include the Ute Trail, the Lost Man Trail, and the famous Maroon Bells Scenic Trail.

Winston-Salem is not a hiking destination.

Is the Shopping Better in Winston-Salem or Aspen?

Winston-Salem
Aspen

Aspen is notable for its shopping areas. Also, Winston-Salem is not as famous, but is still a good city to visit for shopping.

Browsing through shops is a popular activity in Aspen. There are many great local shops and art galleries where you can pick interesting items or fine art.

Plenty of visitors enjoy shopping while in Winston-Salem. You'll find a mix of larger shopping malls, retail outlets, and shopping centers around town.

Is Winston-Salem or Aspen More Beautiful?

Winston-Salem
Aspen

Aspen is notable for its scenery and beauty. However, Winston-Salem is not a destination known for its beauty.

With stunning beauty, Aspen attracts visitors from all around. Surrounded by the mountains and set amongst a beautiful natural setting, this town will take your breath away.

Winston-Salem is not a destination known for its beauty.


Is Winston-Salem or Aspen Better for Families?

Winston-Salem
Aspen

Kids will enjoy a visit to either Winston-Salem or Aspen.

Winston-Salem is a family-friendly place to visit. There are interactive museums like the Kaleideum science museums. There are also outdoor parks and playgrounds, kid-friendly restaurants, and a children's theater.

Aspen is a family-friendly city. Families that enjoy skiing together, hiking, rock climbing, and having adventures will enjoy a visit to this town. Aspen Mountain is not a great option for beginning skiers, but further away, Aspen Snowmass offers good beginner slopes.

Is Winston-Salem or Aspen Better for Couples?

Winston-Salem
Aspen

Aspen is notable for couples. However, Winston-Salem is a mediocre city for romance.

Aspen is a very popular place to visit for couples. Aspen is both a popular ski destination as well as an established town. There are many great restaurants and activities that couples can enjoy and the setting is cute and very scenic, making it a beautiful and romantic destination.

Winston-Salem is not the best destination for a couple to visit. There are restaurants and movie theaters that make for a nice date night. There are also parks and walks that will get you outdoors.

Is Winston-Salem or Aspen Better for Students?

Winston-Salem
Aspen

Winston-Salem is a city with good options for students. However, Aspen is not popular with students.

Winston-Salem is popular with students. Wake Forest University as well as colleges such as Salem College give parts of the city a collegiate vibe.

Aspen is not popular with students.


Is Winston-Salem or Aspen Better for Public Transit? Which Is Easier to Get Around Without a Car?

Winston-Salem
Aspen

Aspen is a popular place for its public transit. However, Winston-Salem is a mediocre city for times when you don't have a car.

Aspen has a few public transit options. There are several shuttle buses around the town.

Public transit is mostly limited in Winston-Salem. There are bus routes, but they are limited in their frequency and convenience, making a car essential for most visitors.

Is Winston-Salem or Aspen a more walkable city?

Winston-Salem
Aspen

Aspen is notable for its ease of walking around. However, Winston-Salem is a mediocre city for its walkability.

Aspen is a very walkable destination. The town is compact enough that it can be explored on foot. If you're planning to head into the mountains to hike, you'll likely need a car.

Winston-Salem is generally not a very walkable city. The downtown area is the most pedestrian-friendly part of town, but most of the city requires a car.

For even more information, also check out Is Winston-Salem Worth Visiting? and Is Aspen Worth Visiting?.

Should I spend more time in Aspen or Winston-Salem?

How long in Winston-Salem or Aspen?

In either Winston-Salem or Aspen, you'll find plenty of activities to fill your time. Most visitors tend to spend more time in Aspen than Winston-Salem because of the overall number of sights and activities. Usually, 1-2 days is a good amount of time for Winston-Salem, and 3-5 days is enough time in Aspen.

Families should spend more time in Aspen than Winston-Salem. Because of the many family-friendly attractions and fun things to do for kids in Aspen, it's a great place to visit with the whole family.

Couples should spend more time in Aspen than Winston-Salem. You'll find plenty of romantic sights and fun activities in Aspen that are perfect for a weekend getaway or a longer couple's trip.

Backpackers and budget travelers should spend more time in Aspen than Winston-Salem if your budget allows for it. With a larger number of budget-friendly sights, good nightlife, and active things to do, anyone traveling on a budget would have a good time in Aspen.


  • How many days in Winston-Salem or Aspen? Ideal Length of Stay
    Winston-Salem 1-2 
    Aspen 3-5

One day in Winston-Salem or Aspen?

In Winston-Salem, many people enjoy the shopping and museums that this friendly destination offers. This city offers a variety of activities to choose from. Because of this, one day is usually enough time for a trip here.

Even though Aspen is a small town, it has plenty of activities to choose from. It's also a relaxing resort destination. Your budget might influence how long you stay. Since there is so much to do in the area, one day is probably not enough for all of it.


A weekend in Winston-Salem or Aspen?

It's hard to know how much time to spend in Winston-Salem. For many, it makes a great getaway for a weekend. This would be the perfect place to spend a weekend, as it has just the right amount of activities. The length of your ideal trip is an individual decision.

It's hard to know how much time to spend in Aspen. Make sure you spend some time hiking while you're in the area. It has many unique tourist attractions and fascinating things to do. A weekend is usually not enough time for a trip here as there is plenty to do.

Five days in Winston-Salem or Aspen?

Winston-Salem is a fun place to experience. Travelers enjoy the nightlife and food when visiting the destination of Winston-Salem. Most people find that five days is more than enough time to see everything.

Aspen is a small town with plenty to do. Travelers enjoy the resorts in the area as well. This ski town offers a variety of activities to choose from. If you have five days, this is a great place to go. Five days is usually enough time to experience most activities.

A week in Winston-Salem or Aspen?

You'll find food and shopping around the welcoming destination of Winston-Salem. Take your pick from the many activities offered here. One week is plenty of time to see everything, even with extra days to spare.

Aspen is a small town, so you can explore the area with less time. People often spend their time relaxing at one of the resorts. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. The length of your ideal trip is an individual decision.


For some great organized tour ideas, see The Best Train & Rail Tours in United States of America, The Best Sightseeing Tours in United States of America, The Best Cruise Tours and Packages in United States of America, and The Best Cultural Tours in United States of America.


Which place is cheaper, Aspen or Winston-Salem?

These are the overall average travel costs for the two destinations. These travel costs come from the actual spending of real travelers.

  • Winston-Salem Prices
    USA Prices
    Aspen Prices
    USA Prices
  • Average Daily Cost Per person, per day
    Winston-Salem $181
    Aspen $355

The average daily cost (per person) in Winston-Salem is $181, while the average daily cost in Aspen is $355. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Winston-Salem and Aspen in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Winston-Salem $91
    Aspen $170
  • Accommodation Typical double-occupancy room
    Winston-Salem $182
    Aspen $340
Compare Hotels in Winston-Salem and Aspen

Looking for a hotel in Winston-Salem or Aspen? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Winston-Salem


Hotels in Aspen


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Winston-Salem Hotel Prices and Aspen Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Winston-Salem $23
    Aspen $56

Hired Cars and Shuttles in Aspen

Some specific examples of transportation prices in Aspen:

  • Aspen hotel or address to Denver Airport (DEN) - Departure Private Transfer: $143

Is it cheaper to fly into Winston-Salem or Aspen?

Prices for flights to both Aspen and Winston-Salem change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Winston-Salem $73
    Aspen $146

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Winston-Salem $20
    Aspen $45

Tours and Activities in Winston-Salem

Some specific costs of activities, tours, and entrance tickets for Winston-Salem are as follows:

  • Old Salem's Ghost Self Guided Outside Walking Tour: $7.75
  • Winston-Salem Historic Guided Walking Tour: $19
  • Winston-Salem True Crime Tour: $19
  • Winston Salem African American History Tour: $19
  • Carolina History & Haunts Winston-Salem Historical Ghost Tour: $26

Tours and Activities in Aspen

Here are a few actual costs in Aspen for available activities, ticket prices, and tours:

  • Aspen Self-Guided Tour: Tales of Wealth, Wildness and Rebellion: $15
  • Aspen Puzzling Adventure: $35
  • Highlights of Aspen Tour: $45
  • Cemetery Tour: $45
  • Aspen's Off the Beaten Path Tour: $45
  • Aspen's Past to Present Historic Tour: $45
  • Aspen's DarkSide Ghost Tour: $45
  • Dark History Ghost-Themed Guided Walking Tour: $45
  • City Highlights Walking Tour: $45
  • Aspen's Off the Beaten Path Scenic Walking Tour: $45
  • From Past to Present History Walking Tour: $45

Alcohol
  • Alcohol Drinks for one day
    Winston-Salem $24
    Aspen $20


When we compare the travel costs of actual travelers between Winston-Salem and Aspen, we can see that Aspen is more expensive. And not only is Winston-Salem much less expensive, but it is actually a significantly cheaper destination. So, traveling to Winston-Salem would let you spend less money overall. Or, you could decide to spend more money in Winston-Salem and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Aspen would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Aspen than you might in Winston-Salem.

If you're trying to decide if either of these two destinations are within your price range, also see Is Winston-Salem Expensive? and Is Aspen Expensive?.


Which is Bigger, Winston-Salem or Aspen?

Winston-Salem has a larger population, and is about 30 times larger than the population of Aspen. When comparing the sizes of Winston-Salem and Aspen, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.