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The best time of year to visit Eureka Springs is probably during the spring. Though some people have different opinions, the spring offers the best weather, before it gets too hot and humid in the summer, and after the colder months have faded from the winter. Even though most events and activities are open all year round, it is nice to do them in pleasantly warm weather. You need to keep in mind, however, that with the warmer weather brings more and more visitors. It can be hard to get hotels and rental cars, so you should try to book your vacation in advance. Still, the city doesn't get that overcrowded and you'll still be able to have a good time. The restaurants will still have good service and you won't have to wait in ridiculously long lines. Also, when it gets a bit busier, the prices for tours tend to drop a bit because there are more people, so the companies can afford to charge a bit less. A lot of the activities in the Ozarks take place outdoors, and so you'll want good weather when you are doing them. There are also festivals and other outdoor activities in the town itself that occur all year long, so you don't have to worry about missing certain events.
Some people love Eureka Springs in the winter. Some of the largest, most beautiful snow fall can be seen in Eureka Springs. If you rent a cabin make sure it has a fireplace, this can make for some romantic evenings. There are not many tourist in Eureka Springs in the winter and it is a nice change of pace for this tourist town. With less traffic, riding a bike all around downtown is an option. Or just go during all the seasons - there's always something to see.