Larger cities, such as Milwaukee and Madison, have a growing population of dog-friendly establishments, many of which have a sunny patio to eat and drink on, and may also feature some dog-friendly food or drink options. Do some research and figure out what establishments nearby may provide a new place for you and your pooch to hang in public.
Milwaukee, Wisconsin is the unofficial frozen custard capital of the world and they have fro-yo and ice cream to boot - and other Wisconsin cities aren't far behind! Take your dog out for a taste of some of the best around. Just make sure they aren't lactose intolerant or eat too much, as the excess sugar still isn't great for their health (or yours), even if it makes one of the best summer treats ever. Dog friendly treats are a must, as additives like xylitol are highly toxic to dogs.
Wisconsin is home to a significant number of killer bike trails and chances are you probably aren't too far from one, even in some of the state's most remote areas. Look online for a bike map, find a route and hit the trails with your high-held tails!