Door County Trolley Tours


One of the many unique elements about Door County is all the locally owned and operated wineries. For a cold-weather climate, who knew that growing grapes to make wine would even be an option? While there are countless wineries for you to choose from, the Door County Trolley Tours provide you with the opportunity to visit and try some wine all within a few hours.

I have had the opportunity to partake in many Door County Trolley Tours over the years and needless to say, it’s a great way to see and experience what Door County has to offer. The Door County Trolley offers an array of tours including scenic (lighthouses, spring blossom), ghost, wine, spirits and brunch tours (just to name a few).

Things I love about the Door County Trolley Tours

The Trolley Drivers
Sitting on a trolley with a bunch of strangers for a few hours can seem overwhelming and boring sometimes, but the trolley drivers break the ice and make it fun! Not only do they play great tunes throughout the journey (shoutout to Alex for letting us control the jukebox once), but they also give insight and history to the area during the drive (with a little humor of course). They make the drive between stops engaging and fun, but most of all they keep everyone on track (and on time!) so that you get the most of out of your trolley experience.

Variety of wineries, pubs & brewhouses
I have partaken in a lot of tours during my Bachelorette party days, and I have never been to the same winery, pubs & brewhouse twice. There are so many different places to experience in Door County and I feel like the trolley really makes an effort to have you experience and see the best places in the county. You won’t find a bad stop in the whole agenda, I guarantee it.

Seasonal Tours
The Trolley Tours cover all of the seasonal events that make Door County so magical. In the fall, the ghost tours and scenic tours allow you to take in the breathtaking colors while getting mildly spooked! During the winter months, the sleigh/carriage ride tours allow you to see the beauty of winter in Door County while drinking great wine and enjoying the fresh winter air. In the spring, enjoy the cherry blossoms and check out a scenic tour of the lighthouses.

The Views of Door County
If there is one thing that sets Door County above the rest (in my opinion), it’s the landscape in which makes it uniquely memorable. The Trolleys take all of the back, winding roads so you can truly see the landscape that makes Door County special. Rolling hills, beautiful glens, breathtaking views of the lake; they make sure you see it all. If there is any trip where you should really put your phone away to truly take it all in, it’s this one.

Things to be aware when partaking in a Door County Trolley Tour

Book your tickets in advance and arrive early
These trolley tours book up really quick especially during the summer months. If you are not a planner, this is not what you will want to hear, but you need to book your tickets well in advance. There have been many times where we have been up there, looking for something to do… we look at a trolley tour one minute and then when we go to book an hour later, and the tour is sold out and seats are gone!

The trolley station has a ton of really good Door County knickknacks, apparel, etc. for trolley riders to buy. I highly recommend you arrive early to look through the shop, buy yourself a cocktail (bring your own insulated tumbler – you’ll thank me later) and mill around a bit before your trolley departs because it gets really busy and crowded inside very fast.

Beware, shopping is involved
If you are looking for a tour that is going to take you to five wineries, breweries or pubs with nothing in between then this tour isn’t for you. Majority of the tour stops go to wineries and/or places with shopping nearby. If you’re looking for short, quick stops where you can try all the wine, I would personally recommend you hire a friend to drive you around. These tours usually include 2-3 stops and include downtime to shop and enjoy. If leisurely tours are not your thing, then the trolleys are not for you.

Lunch is not included on every tour
If you love day drinking, but not on an empty stomach then you should see if your tour package includes lunch. You can get yourself into a whole heap of trouble if you don’t eat beforehand; therefore, I would recommend eating before you go. Some tours do offer lunch at the English Inn (salad, sandwich or pasta options available), but majority of the tours do not. Highly recommend planning ahead since the key to a great day of day drinking is a full stomach.

Revenge of the Bachelorette Parties
With Door County now becoming the Wisconsin destination for Bachelorette parties, just know there is a really high chance there will be one party if not more, on your trolley (especially if there is drinking involved). As someone who has been a member of these groups multiple times, they are usually always on their best behavior, but just note there always tends to be a lot of them and they can sometimes get loud & rowdy.

There are so many great activities to do and experience throughout Door County, and the Door County Trolley Tours is one way to experience some of the best the Cape Cod of the Midwest has to offer. If you’re planning your next trip to Door County and want to find a great place to stay so you can get the best experience possible without missing out on the comforts of home, come check out our property and book direct with us and save!

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