Check the weather reports for the last few years. That will give you a heads-up on “safer” dates, though weather is notoriously unpredictable in Wisconsin.
Explore ordinances and other rules that apply to your site. Some towns, for example, have late-evening noise restrictions.
Work with a reputable lawn care company to spray for pesky bugs like mosquitoes, fleas and gnats and, if applicable, mow the grass several times before the event. Consider providing guests with individual bug spray bottles.
Pay attention to details—in most cases, every chair, table, flower, musical instrument, piece of flooring, fork, knife and spoon will have to be brought to your site.
Understand how much you can spend. Keep a “reserve” fund for the unexpected needs.
Find vendors, like caterers and bands, who are experienced and comfortable working outdoors. Make sure you know what kind of technical needs they have—a generator or two, for example.
Think about the event from a guest’s point of view. Walk the site and make sure you are considering how they will interact throughout the event.
Come prepared for weather-related situations. For instance, bring golf umbrellas for escorting guests between a tent and other areas in case of rain.
Plan for air conditioning or heating (and sometimes both) if your wedding is likely to include some extreme weather. Weddings in May, June, September and October are most likely to include the most varying weather temperatures and both heating and air conditioning may need to be reserved until the week ahead.
Think about lighting, both for safety and decor. Make sure your guests will have well-lit paths to take them to their cars and to the restrooms.
Consider the wind direction and whether side walls for your tent need to be up in some areas to protect table settings and guests. Most are relatively simple to take down an hour before the reception if they aren’t wanted.
Keep antibacterial wipes at the bar for any unexpected cleaning needs.
Reserve backup equipment (a tent for the ceremony or a tented “hallway” in case of rain, heaters or air conditioners, or the like) with a rental company that allows you to release the equipment 48 hours prior to the event without any charge. It allows you to be prepared without incurring unnecessary costs if they aren’t needed.