Fall getaway in Lake Geneva- Day 1

Sunday 10/18/26

Good morning! Coming at you from my cozy inn in Williams Bay (just a few minutes from the resort town of Lake Geneva, WI), where I’m currently enjoying a cup of hot tea, an absolutely delicious banana nut muffin, a big fire in the fireplace, a fall You Tube channel with soft music and a little writing time. Basically a dream morning. 😍

Yesterday we hit the road by late morning and opted to take the “scenic route” (1 hr 18 min from home) versus the interstate route (1 hour flat).

Check in wasn’t until 3, so we had planned a fun fall afternoon first.

First stop was Apple Barn Orchard and Winery, about 20 minutes from Lake Geneva, in Elkhorn, WI. I’d never been here before but I wanted to stop at a place like this (Wisconsin has MANY this time of year), and it was en route and looked cute! Turns out they were having “Pumpkin Fest” with live music and other special events.

I feel like the pictures don’t really do it justice, but it felt like a scene out of a Hallmark movie, haha. You know how in those movies the small towns seem to have a LOT of “holiday festivals” where the big city girl and the small town guy meet….

We weren’t looking to head out to the apple orchard or pumpkin patch, but I mostly just wanted to browse in the fall country store and get a couple of fall treats. The store was super cute and festive!

After that we headed outside to buy a half dozen apple cider donuts, then waited in line at the coffee truck to buy a hot apple cider.

We were planning to get a late lunch in Lake Geneva, so we just shared a donut and cider as a little snack.

It was also a beautiful day!! Albeit rather windy, but in the low 60s with full sunshine and blue skies. It was the perfect little stop off, especially since our boys are pretty past the whole “pumpkin patch” thing now. It was fun and different to go to a fall farm with just Ivan!

We hit the road and drove another ~20 min to downtown Lake Geneva. We were hungry by now for actual lunch and went straight to Flat Iron Tap, a bar/grill that I had caught my eye when researching. It was just right for what I was envisioning! Super cute and cozy (and crowded- we ended up snagging the last 2 spots at the bar, which actually was great because we legitimately enjoy sitting at the bar rail).

I had an Oktoberfest, because, of course! Fit right into my fall weekend theme. 😉

We chatted and watched some of the Bears game (being very close to Illinois + Lake Geneva being home to a lot of Chicago money = there are a LOT of Bears fans here, sadly… 😆).

We then shared THE BEST EVER grilled chicken sandwich with fresh guac, habanero cheese, and fresh jalapenos. It was soooo good! And the seasoned fries were amazing. Trust me, I’ve been to many a bar/grill, and this food was incredible.

After lunch we wandered around Main St for a bit and went into a few shops.

In one gift shop these two signs made me laugh… I snapped a pic of the first one to send to my sister because I am sure she can relate. lol. (Shortly after I took a picture of it, I saw another mom chuckling to herself and taking a picture of it, too. 😅) The other one cracked me up; I sent it to Sarah because we both have strong family histories of dementia, and we always joke that we will end up in the loony bin together one day. 😆(NOT that dementia is actually funny… but you know what I mean! Gotta keep a light heart about things we can’t really control…).

I enjoyed browsing in a cute bookstore, with this little book nook outside with an arch made out of books!

We then made our way to the lakeshore path, which is probably Lake Geneva’s claim to fame. It’s actually a 26 mile long loop- which we did NOT complete, lol.

We just started walking and went about 20-25 minutes before turning around and heading back. It was perfectly lovely!!

Lake Geneva is lined with GORGEOUS homes (many I would definitely consider… estates?). The lakeshore path winds right behind them so it is fun to walk along and decide which one I might like in my future fantasy life where I’m a multimillionaire. 🤔

I didn’t get many pictures because I felt weird taking pictures of people’s homes, lol! (What if they were looking out their window and saw me?! 🫢) There was a real estate office in town though with some listings plastered in the window. Ivan pointed out one he liked that was listed at only 2.75 million… I then said, Ooh I like that top one! When we looked more closely, we saw the list price was $9.25 million. Ivan rolled his eyes and said, OF COURSE you’d pick the 9 million one…. 😅😅🤷‍♀️

The leaves are a bit hit or miss! I think our super hot fall messed up the leaf timing a bit. Usually peak leaves are around now, but I felt like there were still a LOT of green leaves, unfortunately. Oh well. There were still some colors.

This is a good example of how the trees are this year- some trees are already bare, some are still fully green, and some have beautiful color! Kinda weird!

After our very enjoyable walk, we poked around in a couple other shops in town. One of my favorites was this eclectic mercantile shop with decor and things from all around the world.

By this point it was already after 5, so we headed to our hotel (about 10 minutes from downtown).

It’s an adults-only inn which is perfectly charming!

The little porch outside our room.

Our room is so cute and cozy! Just exactly what I was hoping for. 🙂 Our own fireplace, a view out to woods behind, and just so comfy.

Outside patio:

We unpacked and then stretched out to just relax for a while! I half read/ half dozed/ half watched some football.

At a little after 7, we got up and changed into our Packers sweatshirts and took a dorky mirror selfie 😉 before heading to a nearby bar to watch the 7:20 Packers/ Cowboys game!

The place I found was just a ~3 minute drive away and was so perfect! Also super cozy and cute, dim light, etc.

We were not really hungry for a full dinner since we’d had a late lunch but started with a beer and then later ordered some Wisconsin cheese curds to share!! Mmmm they were delicious.

We stayed until the end of the 3rd quarter and then scooted back to the inn to watch the 4th quarter. I was getting sleepy sitting there and wanted to just watch the rest from my bed.

I feel like we fit a ton of fall fun in on this first day and am super happy with our choice to come here. I also am excited to have identified a great getaway place only an hour from home! I would TOTALLY come back to this inn.

Alright, more later!