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

Should you visit Portland, Maine or Woodstock?

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

Should I visit Portland, Maine or Woodstock? 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: Portland, Maine or Woodstock?

Portland, Maine

The largest city in the U.S. state of Maine, Portland has much to offer with its most visited areas being the historic Old Port and the Arts District. They are a mix of the old and new, with a historic feel of the waterfront port versus the contemporary culture of the local art scene. In addition to these popular locations, the Portland area is marked with historical landmarks and museums, places to shop, award-winning restaurants, and activities in areas just outside the city as well.

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.

For some great organized tour ideas, see The Best 10-Day Tours in United States of America, The Best One Week (7-Day) Tours in United States of America, The Best 2-Week Tours in United States of America, and The Best 3-Week Tours in United States of America.

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

Which is Bigger, Portland, Maine or Woodstock?

Portland, Maine has a larger population, and is about 30 times larger than the population of Woodstock. When comparing the sizes of Portland, Maine and Woodstock, 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 Portland, Maine or Woodstock?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Portland, Maine or Woodstock in the Summer?

The summer attracts plenty of travelers to both Portland, Maine and Woodstock. The summer months attract visitors to Portland, Maine because of the beaches, the hiking, and the family-friendly experiences.

In the summer, Portland, Maine is cooler than Woodstock. Typically, the summer temperatures in Portland, Maine in July average around 69°F (20°C), and Woodstock averages at about 74°F (24°C).

People are often attracted to the plentiful sunshine in Woodstock this time of the year. In Portland, Maine, it's very sunny this time of the year. Portland, Maine usually receives around the same amount of sunshine as Woodstock during summer. Portland, Maine gets 282 hours of sunny skies, while Woodstock receives 293 hours of full sun in the summer.

In July, Portland, Maine usually receives less rain than Woodstock. Portland, Maine gets 2.6 inches (66 mm) of rain, while Woodstock receives 3.4 inches (87 mm) of rain each month for the summer.

Should I visit Portland, Maine or Woodstock in the Autumn?

The autumn brings many poeple to Portland, Maine as well as Woodstock. The hiking trails, the shopping scene, and the natural beauty of the area are the main draw to Portland, Maine this time of year.

In October, Portland, Maine is generally cooler than Woodstock. Daily temperatures in Portland, Maine average around 49°F (9°C), and Woodstock fluctuates around 53°F (12°C).

In the autumn, Portland, Maine often gets around the same amount of sunshine as Woodstock. Portland, Maine gets 196 hours of sunny skies this time of year, while Woodstock receives 197 hours of full sun.

Portland, Maine usually gets more rain in October than Woodstock. Portland, Maine gets 3.3 inches (84 mm) of rain, while Woodstock receives 3 inches (77 mm) of rain this time of the year.

Should I visit Portland, Maine or Woodstock in the Winter?

Both Woodstock and Portland, Maine are popular destinations to visit in the winter with plenty of activities. Many travelers come to Portland, Maine for the Christmas ambience, the shopping scene, and the cuisine.

Woodstock can get quite cold in the winter. Be prepared for some very cold days in Portland, Maine. Portland, Maine is much colder than Woodstock in the winter. The daily temperature in Portland, Maine averages around 21°F (-6°C) in January, and Woodstock fluctuates around 25°F (-4°C).

Portland, Maine usually receives around the same amount of sunshine as Woodstock during winter. Portland, Maine gets 163 hours of sunny skies, while Woodstock receives 167 hours of full sun in the winter.

In January, Portland, Maine usually receives around the same amount of rain as Woodstock. Portland, Maine gets 3.4 inches (86 mm) of rain, while Woodstock receives 3.3 inches (83 mm) of rain each month for the winter.

Should I visit Portland, Maine or Woodstock in the Spring?

Both Woodstock and Portland, Maine during the spring are popular places to visit. Many visitors come to Portland, Maine in the spring for the beaches and the natural beauty.

In the spring, Portland, Maine is much colder than Woodstock. Typically, the spring temperatures in Portland, Maine in April average around 43°F (6°C), and Woodstock averages at about 49°F (10°C).

In Woodstock, it's very sunny this time of the year. It's quite sunny in Portland, Maine. In the spring, Portland, Maine often gets around the same amount of sunshine as Woodstock. Portland, Maine gets 212 hours of sunny skies this time of year, while Woodstock receives 227 hours of full sun.

Portland, Maine usually gets less rain in April than Woodstock. Portland, Maine gets 3.3 inches (85 mm) of rain, while Woodstock receives 3.7 inches (95 mm) of rain this time of the year.

Typical Weather for Woodstock and Portland, Maine