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

Should you visit Woodstock or Kailua-Kona?

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

Should I visit Woodstock or Kailua-Kona? 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 Kailua-Kona?

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.

Kailua-Kona

Kailua-Kona, often simply called Kona, is a vibrant seaside town located on the west coast of Hawaii’s Big Island. Known for its sunny weather, beautiful beaches, and laid-back atmosphere, Kona offers travelers an appealing mix of natural beauty and Hawaiian culture. The town is famous for its historic waterfront, local coffee farms, and as the gateway to many of the island’s unique adventures. Despite its popularity, Kailua-Kona remains more relaxed and less crowded than some of Hawaii’s other tourist hubs. Beach lovers, water sports enthusiasts, history buffs, and foodies will all find plenty to enjoy here. With a mix of affordable accommodations, local eateries, and free or inexpensive attractions, it’s a great destination for budget travelers. The nearby volcanic landscapes, snorkeling spots, and lively marketplaces make it an excellent base for exploring the west side of the Big Island.

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

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

Which is Bigger, Woodstock or Kailua-Kona?

Kailua-Kona has a larger population, and is about 5 times larger than the population of Woodstock. When comparing the sizes of Woodstock and Kailua-Kona, 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 Kailua-Kona?

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 Woodstock or Kailua-Kona in the Summer?

Both Kailua-Kona and Woodstock are popular destinations to visit in the summer with plenty of activities.

Woodstock is around the same temperature as Kailua-Kona in the summer. The daily temperature in Woodstock averages around 74°F (24°C) in July, and Kailua-Kona fluctuates around 78°F (25°C).

The sun comes out a lot this time of the year in Woodstock. Woodstock usually receives more sunshine than Kailua-Kona during summer. Woodstock gets 293 hours of sunny skies, while Kailua-Kona receives 169 hours of full sun in the summer.

In July, Woodstock usually receives more rain than Kailua-Kona. Woodstock gets 3.4 inches (87 mm) of rain, while Kailua-Kona receives 2.3 inches (58 mm) of rain each month for the summer.

Should I visit Woodstock or Kailua-Kona in the Autumn?

Both Kailua-Kona and Woodstock during the autumn are popular places to visit.

In the autumn, Woodstock is much colder than Kailua-Kona. Typically, the autumn temperatures in Woodstock in October average around 53°F (12°C), and Kailua-Kona averages at about 78°F (26°C).

In the autumn, Woodstock often gets more sunshine than Kailua-Kona. Woodstock gets 197 hours of sunny skies this time of year, while Kailua-Kona receives 138 hours of full sun.

Woodstock usually gets more rain in October than Kailua-Kona. Woodstock gets 3 inches (77 mm) of rain, while Kailua-Kona receives 1.6 inches (41 mm) of rain this time of the year.

Should I visit Woodstock or Kailua-Kona in the Winter?

The winter attracts plenty of travelers to both Woodstock and Kailua-Kona.

Woodstock can be very cold during winter. In January, Woodstock is generally much colder than Kailua-Kona. Daily temperatures in Woodstock average around 25°F (-4°C), and Kailua-Kona fluctuates around 74°F (23°C).

Woodstock usually receives around the same amount of sunshine as Kailua-Kona during winter. Woodstock gets 167 hours of sunny skies, while Kailua-Kona receives 158 hours of full sun in the winter.

Kailua-Kona receives a lot of rain in the winter. In January, Woodstock usually receives less rain than Kailua-Kona. Woodstock gets 3.3 inches (83 mm) of rain, while Kailua-Kona receives 3.9 inches (100 mm) of rain each month for the winter.

Should I visit Woodstock or Kailua-Kona in the Spring?

The spring brings many poeple to Woodstock as well as Kailua-Kona.

Woodstock is much colder than Kailua-Kona in the spring. The daily temperature in Woodstock averages around 49°F (10°C) in April, and Kailua-Kona fluctuates around 74°F (24°C).

People are often attracted to the plentiful sunshine in Woodstock this time of the year. In the spring, Woodstock often gets more sunshine than Kailua-Kona. Woodstock gets 227 hours of sunny skies this time of year, while Kailua-Kona receives 134 hours of full sun.

Woodstock usually gets more rain in April than Kailua-Kona. Woodstock gets 3.7 inches (95 mm) of rain, while Kailua-Kona receives 3 inches (76 mm) of rain this time of the year.

Typical Weather for Kailua-Kona and Woodstock