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

Should you visit Winston-Salem or Portland?

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

Should I visit Winston-Salem or Portland? 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 under-rated, welcoming, and friendly city. Other reasons to visit include food, shopping, and museums.

Portland

Portland is a laid-back, progressive, and quirky city. It's a very nice small town not to be missed. It offers plenty of beauty for visitors. Other popular activities here include nightlife, live music, and hiking.

Winston-Salem and Portland: Pros and Cons

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

You'll generally find more things to do in Portland than Winston-Salem. Portland is bigger than Winston-Salem, and it also has more attractions and activities for travelers. Portland is better known for its music, hiking, small town charm, and impressive beauty, while Winston-Salem is more popular for its museums, food, and historical sights. Portland is more touristy than Winston-Salem and is popular for its independent and vintage shops, thriving art scene, lush parks and gardens, progressive and quirky personality, and easy access to amazing natural beauty. Also, Portland is famous for Washington Park. Winston-Salem is well known for it's southern character and quaint college campuses.

How is Winston-Salem different from Portland?

Which is Better for a Holiday?

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

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

Winston-Salem is a city with good options for its museums and history. However, Portland is lacking in good options for its museums and landmarks.

Winston-Salem is a good place to visit if you're interested in museums or other recognizable sights. 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.

Portland offers a handful of options for museums and historical sights. Visitors usually come for the city's outdoor recreation and eclectic personality more than the landmarks and museums. There are a few places to visit on a rainy day though including Pittock Mansion, the Portland Art Museum, and the Oregon Museum of Science and Industry.

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

Winston-Salem is a city with good options for its restaurants. However, Portland is lacking in good options for its restaurant scene.

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.

You'll find the standard options when it comes to food in Portland. The town is more famous for it's craft beer than it's food, but there are still a number of local restaurants that offer unique Oregon dishes. You'll find no shortage of vegetarian and vegan options on most menus. There is also a big farm-to-table scene with many farmers markets around town as well.

Is Winston-Salem or Portland Better for Nightlife?

Evening events are notable in both Winston-Salem and Portland.

There's a variety of activities in the evening in Winston-Salem. Local breweries are popping up around town. You'll also find active nightlife venues near the colleges and universities.

With a handful of venues, visitors can find a fairly lively vibe in Portland. Famously, this town's nightlife is all about the craft beer and local breweries. Make sure you check out Bailey's Taproom, The Big Legrowlski, and The Commons Brewery.

Is Winston-Salem or Portland Better for Music?

Portland is a popular place for its music scene. However, Winston-Salem is not a live music destination.

The music scene in Portland is active and vibrant. The town has a thriving live music and international folk dancing scene.

Winston-Salem is not a live music destination.

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

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

Winston-Salem is a good destination for visiting its old town. 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.

Portland does not have a historic old town.

Is Winston-Salem or Portland Better for Hiking?

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

Portland is a popular spot for hiking. Just outside of town you'll find amazing hikes and stunning natural beauty. In town there are many urban hikes through parks and gardens, but in just a short drive you also have access to Mount Hood and many of the region's most beautiful hikes around the Columbia River Gorge.

Winston-Salem is not a hiking destination.

Is the Shopping Better in Winston-Salem or Portland?

Both Winston-Salem and Portland are notable shopping destinations.

Many visitors go to Winston-Salem to go shopping. You'll find a mix of larger shopping malls, retail outlets, and shopping centers around town.

Plenty of visitors enjoy shopping while in Portland. To fully experience shopping in town, head to the local vendors and thrift shops. There are many vintage clothing shops, book stores, and independent sellers around town. The city is also full of farmers markets. For some of the most interesting shopping, check out the Pearl District, Pioneer Place, Union Way, and Downtown neighborhoods.

Is Winston-Salem or Portland Better for Families?

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

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.

Portland is a family-friendly city. This is an outdoor city by nature, so families will appreciate the many parks and outdoor recreational activities around town. It's easy to fill a couple of days exploring and having fun with the kids. Kid-friendly activities include the zoo, the aerial tram, and several great museums.

Is Winston-Salem or Portland Better for Couples?

Portland is a popular place for couples. However, Winston-Salem is a mediocre city for romance.

Portland is a good city for couples to visit. The laid-back, alternative vibe is fun to explore as a couple. There are independent bookstores, nice parks, and plenty of outdoor activities to choose from. Couples who enjoy an eclectic city, breweries, and nature, will find a lot to do in town.

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 Portland Better for Backpackers and Budget Travelers?

Portland is notable for backpackers. However, Winston-Salem is a mediocre city for backpackers and budget travelers.

Portland is a very popular city for backpackers and budget travelers. The town has drawn young explorers for years, and backpackers who like to step away from the mainstream will feel right at home here.

Winston-Salem is not the best destination for backpackers and budget travelers due to its high prices. It's not on the itinerary for most backpackers.

Is Winston-Salem or Portland Better for Students?

Winston-Salem and Portland are both notable destinations for students and younger travelers.

Winston-Salem is a good city to visit for students. Wake Forest University as well as colleges such as Salem College give parts of the city a collegiate vibe.

Plenty of students visit Portland. It's a young and relaxed city that attracts independent thinkers. There are many bookstores and breweries around town. The cost of living can be a bit high though.

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

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

Portland has a few public transit options. The town has a bus and light rail system as well the Aerial tram.

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 Portland a more walkable city?

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

Portland is a very walkable destination. It is quite walkable, particularly in the tourist areas such as Downtown, Pearl, and Old Town Chinatown.

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 Portland Worth Visiting?.

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

How long in Winston-Salem or Portland?

Visitors can find plenty of fun things to do in both Winston-Salem and Portland. With generally more activities and things to do, visitors tend to spend more time in Portland than in Winston-Salem. Usually, 1-2 days is a good amount of time for Winston-Salem, and 2-3 days is enough time in Portland.

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

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

Backpackers and budget travelers should spend more time in Portland 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 Portland.

One day in Winston-Salem or Portland?

The city of Winston-Salem offers food and shopping. With all of its activities, you can easily fill one day here. It will give you the chance to have new experiences.

Many travelers enjoy the shopping and nightlife when visiting the eclectic destination of Portland. Many visitors also spend a good bit of time hiking. 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 Portland?

Winston-Salem is a popular place that is full of things to see and experience. If you have a weekend, this city makes for a great vacation. While some people choose to spend more or less time in Winston-Salem, a weekend is sufficent for most. Take your pick from the many activities offered here.

It's hard to know how much time to spend in Portland. Make sure you spend some time hiking while you're in the area. It has many unique tourist attractions and fascinating things to do. For many, it makes a great getaway for a weekend. A weekend is usually enough time to experience most activities.

Five days in Winston-Salem or Portland?

Winston-Salem is a popular choice for travelers. Five days is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips. The entire region has so many activities, and you'll want time to do everything.

Travelers enjoy the live music and shopping when visiting the laid-back destination of Portland. Many travelers plan to spend time hiking while in the area. This city offers a variety of activities to choose from. Five days is usually plenty of time to spend here with extra days to spare. With this much time, visitors often visit nearby destinations or take day trips.

A week in Winston-Salem or Portland?

Winston-Salem is a great place to explore. One week is more than enough time to enjoy everything. Take some day trips to nearby places to fill the extra days. This city offers something for everyone.

You'll find shopping and nightlife around the city of Portland. Hiking can easily take up a good amount of your time here, too. 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 2-Week Tours from New York City, The Best 2-Week Tours from Anchorage, The Best 2-Week Tours from San Francisco, and The Best 2-Week Tours from Los Angeles.

When we compare the travel costs of actual travelers between Winston-Salem and Portland, we can see that Portland 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 Portland would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Portland 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 Portland Expensive?.

Which is Bigger, Winston-Salem or Portland?

Portland has a larger population, and is about 3 times larger than the population of Winston-Salem. When comparing the sizes of Winston-Salem and Portland, 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.

When is the best time to visit Winston-Salem or Portland?

Both places have a temperate climate with four distinct seasons. As both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Winston-Salem or Portland in the Summer?

Both Portland and Winston-Salem during the summer are popular places to visit. Many visitors come to Winston-Salem in the summer for the family-friendly experiences. Furthermore, most visitors come to Portland for the hiking, the small town charm, the music scene, and the family-friendly experiences during these months.

In the summer, Winston-Salem is a little warmer than Portland. Typically, the summer temperatures in Winston-Salem in July average around 81°F (27°C), and Portland averages at about 68°F (20°C).

In Portland, it's very sunny this time of the year. It's quite sunny in Winston-Salem. In the summer, Winston-Salem often gets less sunshine than Portland. Winston-Salem gets 273 hours of sunny skies this time of year, while Portland receives 338 hours of full sun.

It rains a lot this time of the year in Winston-Salem. Winston-Salem usually gets more rain in July than Portland. Winston-Salem gets 4.4 inches (112 mm) of rain, while Portland receives 0.7 inches (18 mm) of rain this time of the year.

Should I visit Winston-Salem or Portland in the Autumn?

The autumn attracts plenty of travelers to both Winston-Salem and Portland. Most visitors come to Winston-Salem for the shopping scene during these months. Furthermore, the autumn months attract visitors to Portland because of the hiking trails, the shopping scene, the music scene, the small town atmosphere, and the natural beauty of the area.

In October, Winston-Salem is generally a little warmer than Portland. Daily temperatures in Winston-Salem average around 62°F (17°C), and Portland fluctuates around 55°F (13°C).

In Winston-Salem, it's very sunny this time of the year. Winston-Salem usually receives more sunshine than Portland during autumn. Winston-Salem gets 212 hours of sunny skies, while Portland receives 155 hours of full sun in the autumn.

In October, Winston-Salem usually receives more rain than Portland. Winston-Salem gets 3 inches (75 mm) of rain, while Portland receives 2.6 inches (67 mm) of rain each month for the autumn.

Should I visit Winston-Salem or Portland in the Winter?

The winter brings many poeple to Winston-Salem as well as Portland. The winter months attract visitors to Winston-Salem because of the museums, the shopping scene, and the cuisine. Additionally, the museums, the shopping scene, and the cuisine are the main draw to Portland this time of year.

It's quite cold in Portland in the winter. The weather in Winston-Salem can be very cold. Winston-Salem is around the same temperature as Portland in the winter. The daily temperature in Winston-Salem averages around 40°F (4°C) in January, and Portland fluctuates around 40°F (4°C).

In the winter, Winston-Salem often gets more sunshine than Portland. Winston-Salem gets 169 hours of sunny skies this time of year, while Portland receives 86 hours of full sun.

It's quite rainy in Portland. Winston-Salem usually gets less rain in January than Portland. Winston-Salem gets 3.2 inches (82 mm) of rain, while Portland receives 5.2 inches (132 mm) of rain this time of the year.

Should I visit Winston-Salem or Portland in the Spring?

Both Portland and Winston-Salem are popular destinations to visit in the spring with plenty of activities. Also, many travelers come to Portland for the small town charm and the natural beauty.

In the spring, Winston-Salem is much warmer than Portland. Typically, the spring temperatures in Winston-Salem in April average around 61°F (16°C), and Portland averages at about 51°F (11°C).

It's quite sunny in Portland. The sun comes out a lot this time of the year in Winston-Salem. Winston-Salem usually receives around the same amount of sunshine as Portland during spring. Winston-Salem gets 248 hours of sunny skies, while Portland receives 231 hours of full sun in the spring.

In April, Winston-Salem usually receives more rain than Portland. Winston-Salem gets 3.1 inches (80 mm) of rain, while Portland receives 2.4 inches (61 mm) of rain each month for the spring.

Typical Weather for Portland and Winston-Salem