The Best Places to Propose in Southern Wisconsin

The proposal is one of the most important steps in a relationship. Whether you want it to be a big event, or something small and intimate, it’s one of the first steps you take towards becoming a married couple, and that’s a huge deal ! Knowing this, I thought it would be helpful to talk about some of my favorite places that couples choose to propose here in Southern Wisconsin as well as some tips to planning the proposal itself. Let’s not waste any time and get right into it, starting with the incredible Lake Geneva !

My Favorite Locations for a Proposal in Southern Wisconsin

The Marina of Lake Geneva

The city of Lake Geneva is one of the most beautiful in all of Southern Wisconsin, making it an easy choice when looking for places to propose in the area. Lake Geneva is a wonderful, historic lakefront town with a TON of charm and character. There are so many great spaces to choose from for a proposal here, check out my engagement photo guide to see some of them, but if I had to pick just one it would be the Marina ! Breathtaking views of the lake, a scenic dock to walk along, and the beach and historic downtown just steps away, what more could you want? Sunsets here are ESPECIALLY gorgeous, making for an incredibly romantic setting for your proposal !

At the Wind Point Lighthouse

About 30 minutes north of Kenosha, in the city of Racine, sits the Wind Point Lighthouse, the next location on my list. There are many old and historic lighthouses that still rest on the shores of Lake Michigan (shocker right?), but there’s something special about Wind Point. It’s slightly removed from downtown Racine, giving you a bit of privacy when you pop the question to the love of your life. It also has that classic late 1800’s aesthetic to it that is just SO charming. Combine that with the beautiful park that sits near the lighthouse, and the wonderful views of Lake Michigan and the Wisconsin shoreline, and you have one of the best places to propose in all of southern Wisconsin !

In Petrifying Springs Park

Any frequent readers of my blog will likely recognize the name Petrifying Springs Park, as this is one of my all time favorite locations in the Kenosha area for photos ! Whether it’s for engagement photos, wedding day portraits, or even proposals, there is just SO much beauty to enjoy throughout the park. The abundance of beautiful trails and scenery make practically every inch of this park great for a proposal, though I have a few personal favorite spots that I like to recommend to my couples !

At the Milwaukee Central Library

The next spot on my list is the historic Milwaukee Central Library.  This library was built in the late 1800’s, and features renaissance style architecture that makes it such a wonderful backdrop option for your proposal. It truly is a stunning location, and the best part is that being in Milwaukee gives you SO many additional opportunities for portrait photos after you pop the question. It’s typically much busier here than any other location on the list, but that can be a benefit as it will be much simpler for your photographer to blend in and be inconspicuous !

Literally SO Many Others

There are honestly too many great places to propose in southern Wisconsin to list (if I did we’d have a full 5 part series of novels!) Just know that no matter the style, vibe, and setting you’re after, you can find it here. Whether it’s something modern, historic, natural, urban, quaint, retro, or any other adjective you can think of. I personally don’t photograph too many proposals, but when I do I love working with my clients to help find THE perfect location that best fits the vision they have for the moment ! Speaking of which, let’s talk a little bit more about the planning that goes into a proposal.

Planning the Proposal

Deciding the Where and When

As you begin brainstorming for your proposal, you’ll first want to consider where and when it will take place. Even though we covered some of my favorite places to propose in southern Wisconsin already, there’s still a few more things I’d like to cover here. First is that if you have a location picked out already that is wonderful. Many couples like to include a location, or sometimes an activity, into the proposal that has special ties to them. I for one am ALL for this as it adds another layer of depth, emotion, and personality to your photos ! If that’s not what you’re after though that’s totally fine. Even if you don’t know the specific location that you want to propose at, consider the vibe you want so that when you book a photographer they can recommend some options that fit it.

As for the when, it’s important to consider both the time of day and the season itself. For the season I recommend choosing a time of year that you both enjoy and are comfortable in. If you can’t stand the cold Wisconsin winters maybe don’t have a winter proposal as an example !

For the time of day, the main things to consider are the lighting and how crowded the location will be. Outdoor spaces have much better lighting closer to sunrise and sunset, while midday is best for indoor locations for more natural lighting. As for popularity, places in high density areas like Milwaukee, or tourist destinations like Lake Geneva, are going to be considerably busier at sunset than they are at sunrise. This isn’t necessarily a deal breaker, but it is something to be aware of if you were wanting your proposal to be a private moment between the two of you !

Choosing Your Photographer

I’ve alluded to this a few times throughout the article, but booking the right photographer for your proposal can make a world of difference. You don’t just want someone who can provide fantastic photos of the moment (though that is crucial!), you also want someone who can help ensure that your plan is executed perfectly. The right photographer will be able to provide location suggestions, assist with the timeline of the moment, help you plan how to get your partner to the location, and more. 

Coming Up with the Proposal Plan

One of the most important parts of planning a surprise proposal is coming up with the plan of the moment. Getting your partner to a specific location, on a specific day, at a specific time can be a real logistical challenge, especially if they’re usually the ones that make the plans ! This is another area where planning the location of your proposal is incredibly important. You ideally want to get your partner there without any suspicion. 

Try to come up with a ruse that they’d believe, whether that’s meeting up with friends and they’re running late, or a date night out and you decide to take the scenic route. A great option I love to recommend is booking your photographer for a “couples session” so that they aren’t suspicious as to why someone is taking photos. Some locations are easier for photographers to hide at than others, but this is a surefire way to bring minimal suspicion to the event !

What Happens After

After you propose, and your partner excitedly says yes, it’s time to celebrate ! I strongly encourage you to plan something special for the night in addition to the proposal itself. It can be a dinner with friends and family, a romantic night for just the two of you, or something else entirely. The point is that this is an amazing moment for the two of you and your relationship, and you deserve to celebrate it together !

Those are tips on how to plan your proposal, as well as some of my favorite places to propose in Southern Wisconsin ! After you’re engaged be sure to check out some of my wedding planning tips over on the blog, and if you’d like me to be your photographer be sure to send me an inquiry through my contact page ASAP !