A Travel Price Comparison for United States of America Woodstock vs. Portland for Vacations, Tours, and Honeymoons

Should you visit Woodstock or Portland?

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

Should I visit Woodstock 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.

Where Should I go: Woodstock or Portland?

Woodstock

While this town does lend its name to the 1969 Woodstock Festival, the legendary event was actually held on a dairy farm almost 60 miles away in Bethel, NY. So if you are looking to see the field where it all happened and a museum dedicated to its history, you will need to take a day trip outside of town.

Woodstock, New York, however, does stay true to the spirit of the arts. Since 1903, the place lay home to Byrdcliffe Art Colony, the oldest of its kind in the nation, and even attracted artists of the Hudson River School during the late 1800s. Today, artists from all disciplines-visual, ceramic, music, fiction, nonfiction, screenwriting, playwriting, and poetry-take up residence at the colony and have works displayed in galleries open in the main part of town.

Tinker Street and Mill Hill Road are lined with a mix of restaurants and shops all teeming with the essence of hippie living, arts, and spirituality. From shops selling Woodstock paraphernalia, incense, and Himalayan products, to yoga studios, vegan restaurants, and local art galleries-the town of Woodstock is one dedicated to keeping the spirit of the Woodstock Festival and the arts alive.

Portland

Referred to as "The City of Roses", Portland is the largest city in Oregon. It sits on the banks of the Columbia River and offers breathtaking views of Mount Hood when the weather allows. Portland is famous for its alternative vibe, live music scene, and popular microbreweries. It's also a mecca for environmentally conscious urban planning. The downtown area is quite compact and walkable. While the city itself may be smaller than you expect, it is still the largest metropolitan area between San Francisco and Seattle.

For some great organized tour ideas, see The Best Luxury Tours to United States of America, The Best Tours for Seniors to United States of America, The Best Contiki Tours to United States of America, and The Best G Adventures Tours to United States of America.


Which place is cheaper, Portland or Woodstock?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Woodstock is $154, while the average daily cost in Portland is $180. 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 Woodstock and Portland in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Woodstock $81
    Portland $97
  • Accommodation Typical double-occupancy room
    Woodstock $162
    Portland $194
Compare Hotels in Woodstock and Portland

Looking for a hotel in Woodstock or Portland? 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 Woodstock


Hotels in Portland


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: Portland Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Woodstock $60
    Portland $28

Hired Cars and Shuttles in Portland

Also for Portland, here are a few examples of actual transportation services:

  • Waterfall Express -PDX: Waterfall Trolley Tickets + Transfer: $60
  • Portland downtown to Portland Airport (PDX) - Departure Private Transfer: $61
  • Lake Oswego to Portland Airport (PDX) - Departure Private Transfer: $71
  • Portland Airport (PDX) to Beaverton hotel or address - Arrival Private Transfer: $75
  • Tigard hotel or address to Portland Airport (PDX) - Departure Private Transfer: $75
  • Private Transfer from Portland Airport (PDX) to Astoria Port: $88
  • Portland International Airport - Private transfer from/to Oregon City: $127
  • Portland Airport (PDX) to Lake Oswego - Round-Trip Private Transfer: $142
  • Portland Airport (PDX) to Tigard hotel or address - Round-Trip Private Transfer: $151

Is it cheaper to fly into Woodstock or Portland?

Prices for flights to both Portland and Woodstock 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
    Woodstock $34
    Portland $43

Typical Food Prices in Portland

For Portland, here are some examples of average food and meal prices for travelers:


  • Afternoon Drinks (for 2)
    $9.50

Food Tours and Cooking Classes in Portland

For Portland, here are some samples of tours and activities related to meals and dining experiences:

  • Walking Pizza Tour: $75
  • Secret Food Tour with Local Guide: $94
  • Brunch on Mississippi Food Tour: $95
  • Downtown Portland Food Tour : $99
  • Downtown Food Tour: $102
  • Mississippi Avenue Walking Food Tour: $105
  • The Vibrant Kerns Hood Food Tour: $105
  • The Bustling Buckman Hood Food Tour: $105
  • Portland Walking Food Tour With Secret Food Tours: $109
  • Mississippi Avenue Walking Food Tour: $110
  • All-Inclusive Downtown Portland Food Tour: $119
  • All-Inclusive Walking Food Tour: $119

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Woodstock $35
    Portland $24

Tours and Activities in Portland

For Portland, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • Smartphone Old Port Portland, ME Audio Walking Tour APP/GPS: $6.75
  • Portland, Maine: Walking Tour Audio Guide: $8.49
  • Downtown Portland In-App Audio Tour (ENG): $9.00
  • Scavenger Hunt Adventure Smartphone Audio Guide: $10
  • Waterfront Scavenger Hunt Self-Guided Tour: $13
  • Downtown Scavenger Hunt & Self-Guided Walking Tour: $13
  • Portland (Along the Waterfront) Scavenger Hunt & Self-Guided Tour: $13
  • Portland Exploration: Self-Guided Driving & Walking Tour: $14
  • Self-Guided Sightseeing Driving Audio Tour: $15
  • Portland Scavenger Hunt Adventure: $21
  • Guided Walking Tour of Downtown Portland, Oregon: $23
  • Smartphone-Guided Walking Tour of Downtown Portland: $25

Alcohol
  • Alcohol Drinks for one day
    Woodstock $22
    Portland $17

Sample the Local Flavors in Portland

Some specific costs for nightlife related activities in Portland:

  • Haunted Underground Shanghai Tunnel Tour with Brewery Tastings: $40
  • Portland Ghosts Boos and Booze Haunted Pub Crawl: $40
  • Weird Bar Crawl with Fanatical Local: $59
  • Guided Bike Tour with Brewery Visits: $65
  • Portland, Maine: Old Port Brewery & Pub Walking Tour: $89
  • Portland, Maine: Local Brewery & Spirits Bus Tour: $99
  • Afternoon Tour in Columbia Gorge Waterfall with Free Wine Tasting: $111
  • Waterfalls, Mt Hood, and Wine Tour (Tasting Fees Included): $135
  • Silver Falls Hike and Wine Tour: $179
  • Willamette Valley Wine Tasting from Portland: $189
  • Bed and Breakfast Wine Tour - Small Group, Joinable/Sharable: $198
  • From Willamette Valley Full-Day Wine Tour: $210


When we compare the travel costs of actual travelers between Woodstock and Portland, we can see that Portland is more expensive. And not only is Woodstock much less expensive, but it is actually a significantly cheaper destination. So, traveling to Woodstock would let you spend less money overall. Or, you could decide to spend more money in Woodstock 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 Woodstock.

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


Which is Bigger, Woodstock or Portland?

Portland has a larger population, and is about 250 times larger than the population of Woodstock. When comparing the sizes of Woodstock 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 Woodstock 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 Woodstock or Portland in the Summer?

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

Woodstock is a little warmer than Portland in the summer. The daily temperature in Woodstock averages around 74°F (24°C) in July, and Portland fluctuates around 68°F (20°C).

In Portland, it's very sunny this time of the year. It's quite sunny in Woodstock. In the summer, Woodstock often gets less sunshine than Portland. Woodstock gets 293 hours of sunny skies this time of year, while Portland receives 338 hours of full sun.

Woodstock usually gets more rain in July than Portland. Woodstock gets 3.4 inches (87 mm) of rain, while Portland receives 0.7 inches (18 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Woodstock 74°F (24°C) 
    Portland 68°F (20°C)

Should I visit Woodstock or Portland in the Autumn?

The autumn attracts plenty of travelers to both Woodstock and Portland. Also, 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 the autumn, Woodstock is around the same temperature as Portland. Typically, the autumn temperatures in Woodstock in October average around 53°F (12°C), and Portland averages at about 55°F (13°C).

Woodstock usually receives more sunshine than Portland during autumn. Woodstock gets 197 hours of sunny skies, while Portland receives 155 hours of full sun in the autumn.

In October, Woodstock usually receives more rain than Portland. Woodstock gets 3 inches (77 mm) of rain, while Portland receives 2.6 inches (67 mm) of rain each month for the autumn.


  • Autumn Average Temperatures October
    Woodstock 53°F (12°C) 
    Portland 55°F (13°C)

Should I visit Woodstock or Portland in the Winter?

The winter brings many poeple to Woodstock as well as Portland. Also, 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 Woodstock can be very cold. In January, Woodstock is generally much colder than Portland. Daily temperatures in Woodstock average around 25°F (-4°C), and Portland fluctuates around 40°F (4°C).

In the winter, Woodstock often gets more sunshine than Portland. Woodstock gets 167 hours of sunny skies this time of year, while Portland receives 86 hours of full sun.

It's quite rainy in Portland. Woodstock usually gets less rain in January than Portland. Woodstock gets 3.3 inches (83 mm) of rain, while Portland receives 5.2 inches (132 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Woodstock 25°F (-4°C) 
    Portland 40°F (4°C)

Should I visit Woodstock or Portland in the Spring?

Both Portland and Woodstock 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.

Woodstock is around the same temperature as Portland in the spring. The daily temperature in Woodstock averages around 49°F (10°C) in April, and Portland fluctuates around 51°F (11°C).

It's quite sunny in Portland. The sun comes out a lot this time of the year in Woodstock. Woodstock usually receives around the same amount of sunshine as Portland during spring. Woodstock gets 227 hours of sunny skies, while Portland receives 231 hours of full sun in the spring.

In April, Woodstock usually receives more rain than Portland. Woodstock gets 3.7 inches (95 mm) of rain, while Portland receives 2.4 inches (61 mm) of rain each month for the spring.


  • Spring Average Temperatures April
    Woodstock 49°F (10°C) 
    Portland 51°F (11°C)

Typical Weather for Portland and Woodstock

Woodstock Portland
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 25°F (-4°C) 3.3 inches (83 mm) 40°F (4°C) 5.2 inches (132 mm)
Feb 28°F (-2°C) 3.2 inches (81 mm) 44°F (7°C) 3.9 inches (98 mm)
Mar 38°F (3°C) 3.8 inches (97 mm) 47°F (9°C) 3.6 inches (92 mm)
Apr 49°F (10°C) 3.7 inches (95 mm) 51°F (11°C) 2.4 inches (61 mm)
May 60°F (16°C) 3.5 inches (89 mm) 57°F (14°C) 2 inches (51 mm)
Jun 69°F (21°C) 3.5 inches (90 mm) 64°F (18°C) 1.5 inches (39 mm)
Jul 74°F (24°C) 3.4 inches (87 mm) 68°F (20°C) 0.7 inches (18 mm)
Aug 72°F (22°C) 3.9 inches (100 mm) 69°F (20°C) 1 inches (25 mm)
Sep 64°F (18°C) 3.5 inches (90 mm) 63°F (17°C) 1.7 inches (44 mm)
Oct 53°F (12°C) 3 inches (77 mm) 55°F (13°C) 2.6 inches (67 mm)
Nov 43°F (6°C) 4.3 inches (110 mm) 46°F (8°C) 5.4 inches (136 mm)
Dec 30°F (-1°C) 4.1 inches (103 mm) 40°F (5°C) 6.1 inches (156 mm)