Dells Trolley: Winery Tour

The Winery Trolley Tour is the Dells for adults. Instead of a waterpark queue, you ride a trolley to several wineries in the surrounding Sauk County countryside, taste what each makes and stop for lunch, while someone else handles the driving. According to the operator, the winery tours visit multiple locations and include lunch, and the same company also runs brewery, Bloody Mary brunch and other themed rides. It suits couples, friend groups, birthday and bachelorette parties and anyone who wants to see the Wisconsin wine country around the Baraboo Hills without coordinating a designated driver. The details of which wineries, how long and what is included are set by the operator, so confirm them when you book.

Wisconsin is not the first state people think of for wine, yet the country around Sauk County has a surprisingly long winemaking tradition. The Baraboo Hills and the Wisconsin River valley hold small wineries working with cold-hardy grapes and with fruit wines made from cherries, cranberries, apples and other local crops. A trolley tour is a low-effort way to sample that variety. The format also solves the practical problem of tasting rooms spread across country roads: nobody has to drive, nobody has to ration their sips, and the guide keeps the schedule moving.

A typical winery trolley day, as the operator describes it, runs to several stops with lunch included. Tasting formats vary by winery, so you may sample a flight of dry and sweet wines at one place and enjoy a cheese or charcuterie plate at another. Bring a little extra spending money for bottles you decide to take home, and ask whether the tour allows you to ship wine or buy by the case.

Be honest with yourself about your tolerance: sampling at three stops can add up, and the trolley ride home is a good moment for water and snacks.

Because this is an adults-focused activity, check age rules before you book and plan childcare if you are traveling with a family. Weather matters less than on a boat or a bluff, since tasting rooms are indoors, but road conditions in winter can affect schedules. The Dells is also well known for brewery and dive-bar tours on the same trolleys, so groups that like variety can mix a winery day with an evening ride.

For a different wine-country stop that you can combine with a self-drive day, Wollersheim Winery in Prairie du Sac is the best-known name in the area.

Before you book, ask about the practicalities: which wineries are on the route, how long you stay at each, what tasting fees are included and how lunch works for vegetarians or guests with allergies. Ask about pickup points, since the company runs shuttles and party transportation and may collect groups from resorts.

Plan to eat a decent breakfast, wear comfortable shoes for uneven winery grounds and bring a small cooler bag if you expect to buy bottles on a hot day. Tips for the guide are customary and appreciated, and a group booking often makes the day feel more like a party.