Adam’s and my first year wedding anniversary was at the end of September and we wanted to make sure it was a memorable celebration for us. We thought about doing a staycation in the city, but then decided it’d be a bit more fun to explore a new area that wasn’t too far away from Chicago. We debated Galena in Illinois and areas in Wisconsin, but ultimately landed on heading to western Michigan. It’s a short two to three hour drive from the city and is a perfect area to visit during all four seasons, but especially in the fall. We researched a bunch of different cities along the Lake Michigan coastline, but decided on the gem that is Saugatuck, Michigan.

I had been to Saugatuck twice before in the summertime for bachelorette parties and was pleasantly surprised by the little town. I hadn’t gotten a chance to really explore the art, the shops or the restaurants as much as I would have liked during those times, so I figured our anniversary was the perfect opportunity for Adam and I to do so! We had great fall-like weather the weekend we were there with a crispness to the air and plentiful sunshine. We were both so at ease and relaxed the whole time and I left Saugatuck knowing I would 100% be back again.

If you’re looking for a quick weekend getaway in the Midwest, you’ve landed at the right place. Take a read below to find out the best places to stay, where to eat, and what things you can do while on your trip!

Where to Stay

What I love most about Saugatuck is that when we started looking for accommodation, I noticed most of what we came across were inns and bed and breakfasts. Adam and I had never done an official bed and breakfast, so we decided this was the perfect opportunity. We wanted to stay in town so we could easily walk everywhere and not have to worry about driving as much and finding parking. Lucky for us, there were plenty of options in the heart of town.

We came across the Judson Heath Colonial Inn, which was just a few blocks away from all the shops and restaurants. It was a family home built in 1837 that was recently renovated in 2017 by the sweetest couple, Jen and Steve. Just from the reviews and pictures alone, we knew we had to stay there.

Upon arrival, I was smitten with the home. The old charm was still alive and well in every corner of the house from the original door knobs (we got an actual vintage key to lock and unlock our door!) to the beautiful carved fireplace. It did have some modern touches though, like a rain shower in the bathroom and a Roku TV in the bedroom. We felt so at home as soon as the inn owner, Jen, greeted us and let us inside.

For being an inn, I felt our bedroom was rather spacious and plenty of room for the two of us. They had bottled water on a small table in the room and robes in the armoire available, which I appreciated. The bed was unbelievably comfortable and I got some dreamy sleeps in during our stay. The only negative I would say about the bedroom is that the walls were a bit on the thinner side (it’s an old house, so I get it!) and we were woken up one of the nights by some boisterous guests.

Other than that, our stay was absolute perfection. Jen and Steve have done such an amazing job on not only restoring the home, but also providing some of the best quality service I’ve encountered. I couldn’t recommend Judson Heath Colonial Inn more. They only have eight rooms, so I recommend booking pretty far in advance to nab one of them! Each has their own price as each room is a bit different in terms of size and style. They seemed to all be in the $200-300 range while we were there in late September. I’d assume pricing is a bit more during the summer months.

If Judson Heath doesn’t fit your needs or there are no longer vacant rooms, there are definitely other inns and bed and breakfasts nearby downtown like the Hidden Garden Cottages & Suites and the Wickwood Inn that seem to have stellar reviews as well. These options are a bit on the pricier side too, so if you’re looking to spend less, I’d advise staying on the outskirts of town and staying at hotel like the Best Western.

Where to Eat

Lucky for us, we had a three course breakfast included with our stay at Judson Heath. It seems like most of the inns in town include breakfast with the price of a room, which softens the cost. Because I had never stayed at a bed and breakfast, I was surprised to see that all the inn guests ate at one table. Maybe that’s commonplace, but I had no idea! I was a little nervous to eat with strangers, but it ended up being so fun to chat with them. Many were like us, from Illinois.

Anyways, let’s get to the food. Let me just tell you, I may have had some of the best breakfasts in my life at the Judson Heath Colonial Inn. I’m not even exaggerating. Jen’s and her mother’s cooking is out of the world good. Upon entering the dining area, there’s a coffee and tea station where you can make your own coffee and tea with all the fixings! I chuckled to myself when I saw Rumchata and Bailey’s – a bit aggressive at 9:30am for me, but I thought it was a nice touch for those that maybe need a little more of a boost in the morning 🙂 We then sat down and had some sort of pastry to dig into. I’m not a huge breakfast pastry kinda gal, but I indulged and was so glad I did. I may actually like scones now!

We were then served a fruit with a yogurt cream sauce each of the mornings. The first day we had a poached pear and the second day, a candied plum. I wish I could have had seconds of both.

The main course then came our way. The first day we had a salmon omelette with a topping of salsa, which would never, ever be something I’d order on my own at a restaurant, but was so pleasantly surprised by it. It also came with some delicious breakfast potatoes. The second day was my favorite though, where we were served corn cakes topped with scrambled eggs, chorizo, salsa, avocado and a bit of sour cream. Both were just phenomenal meals.

Adam and I honestly didn’t really need lunch because we were so stuffed for breakfast, so we only ate dinner in downtown Saugatuck. There’s plenty of little shops to pick up snacks or grab lunch though. I recommend just walking around and exploring!

I had done some research beforehand and looked at the best restaurants in Saugatuck for dinner. We decided against making a reservation because we weren’t sure what we’d be in the mood for the day of. We were planning to go to Bowdie’s Chophouse, but the wait was going to be a bit too long for us. There was also the option of Marro’s Italian Restaurant (we weren’t feeling Italian) or Phil’s Bar & Grille (I had been there before on a bachelorette party and thought the food was excellent but wanted to go somewhere different). We decided then on The Southerner, where we could feast on some good ol’ southern comfort food.

It was super cute, relaxed, and spacious inside with wooden tables and chairs. The restaurant sits on the harbor so you can get a nice view of the water and boats going by. We got pretty close to the window and were able to enjoy the sun beginning to set. The food was pretty good – we split fried chicken and mac and cheese, along with collard greens, baked beans, and biscuits. The main dishes and biscuits were delicious, but we were underwhelmed by the sides as they were a little on the colder side and seemed to lack a bit of flavor. It could be that we’ve just been spoiled by Chicago restaurants though too!

On our second night in town, we headed to Uncommon Grounds to grab a hot chocolate since it was a bit chilly. I had been there two times before when I went to Saugatuck for those bachelorette parties and fell in love with the hipster, eclectic vibe, as well as the coffee! Definitely make a stop in if you’re a coffee drinker – it’s super cute in there.

What I love most about Saugatuck is that while it’s so quaint, there are still so many restaurants and options to choose from. And bonus – they are all within walking distance! So, if you do end up staying downtown, there’s really no need to drive.

What to Do

Saugatuck has so many things to do in any season! In the summer, I recommend heading to the pristine Oval Beach which overlooks Lake Michigan. There is an entry fee to park (cash only), so keep that in mind! Oval Beach is a great way to spend a hot summer day. Even better? The sun sets over the lake, which makes for some pretty bomb sunsets. While we were on our anniversary trip, despite the cooler weather, Adam made our way to the beach to watch the sun go down. Because it was offseason and off-hours, there was no fee to get into the parking lot. We walked the beach and curled up on blankets to watch the sun set. It was so peaceful!

Just a bit north of Oval Beach is Saugatuck Dunes State Park. Adam and I didn’t go there, but we heard from some of the other Inn guests that they hiked it and really enjoyed it. There’s a bunch of trails, as well as another beach, which is more secluded. They also have dune buggy rides, which I think would be super fun!

What Adam and I did take part in was the winery situation! There’s a few wineries on the outskirts of Saugatuck in neighboring towns. We opted to go to Fenn Valley Vineyards, as it seemed like the biggest and because they had a band playing outside on the grounds that day! It seems Fenn Valley does that many Saturdays in the summer and early fall.

If going on a busy weekend, I recommend purchasing your tasting fee ahead of time. This way, you get a set tasting time and get priority access to do your tasting! It wasn’t terribly crowded the day we went, but we were able to bypass a few other people and get our tasting first. The woman giving us the tasting was super attentive and fast – we probably finished our tasting in like 15 minutes! Believe it or not, Michigan wine is pretttttty tasty! There were some clear winners in our book and we ended up buying two bottles. After our tasting, we also purchased a meat and cheese board, as well as sparkling wine (in a can!) and took it outside to sit and enjoy the music playing. It was the perfect fall day.

If wine isn’t your thing, the area around Saugatuck also offers the Saugatuck Brewing Company and Virtue Cider, so you definitely have options! I also heard that the Crane Apple Orchard had a beer tasting. If you’re in Saugatuck in the late summer or early fall, definitely head to the apple orchard to get your apple fix. I wish we had had time to go, as we heard all the good things about it from the other Inn guests!

What Adam and I most enjoyed was just walking around downtown Saugatuck and checking out all the cute shops. We did this the Saturday morning we were in town and I just can’t even begin to explain how fun it was. I was definitely in a mood to S-H-O-P! I’ve listed some of my favorite stores on Butler Street below:

• Saugatuck Gallery – Adam and I have been on an art kick the last few months and knowing Saugatuck is an artsy town, we knew we had to stop in here. There were so many beautiful paintings and so many options to choose from. We browsed for awhile and came across a gorgeous oil painting that we knew would be perfect in our kitchen so we decided to buy it. The great thing about this place is they seem to always have paintings at least 50% off. And no, they’re not going out of business – that’s just how they operate! Our painting was originally $125 and we got it for $40! Highly recommend checking it out!
• For the Love of Shoes – I randomly decided to go in here and I’m so glad I did. It’s mainly known for being a shoe store, but they had some women’s clothing in the back where I found a cozy long sleeve shirt that I bought, as well as the comfiest, fluffiest slippers ever. Love! They also had a wide array of cute hats and scarves.
• Glik’s – I happily stumbled into this fashion boutique and was pleasantly surprised. It was a huge store and seemed to have something for everyone. One side of the store was dedicated to men, and the whole other side was dedicated to women but split into a more casual/classic clothing style section and then a bohemian clothing style section. I got the cutest black vest, corduroy skirt, and kimono (which I’ve been trying to find one I like forever!!). I can’t wait to go back to Saugatuck just to go back here.
• Kindel & Company Lifestyle Mercantile {Note: Not on Butler St.} – We decided to go into Kindel & Co and found they had quite a lot of male-focused items. Adam was pretty excited about the after-shave spray he got! Definitely bring your man in here so he can indulge!
• Saugatuck Spice Merchants – This shop was amazing! They had a large array of spices, coffees, and teas to choose from. They also had a bunch of cooking accessories. We purchased the ‘Tuscan’ spice and it has quickly become one of my favorite things ever. I’ve put it on pasta, on veggies, and mixed it with olive oil to dip bread in! Must go!
• Olive Mill – I love, love, loved this shop as well. They had jugs of different flavors of olive oil and balsamic vinegar that you could taste test. Lo and behold, they had a ‘Tuscan’ olive oil and balsamic vinegar. I loved the spice so much and the taste of the oil and vinegar that you bet I got a bottle of each. Can’t wait to go back and restock.

I cannot recommend Saugatuck enough for a quick weekend getaway. It’s a chance to unplug, take in the scenery and nature, indulge in shopping and yummy food and wine and relax. What could be better? I’m already planning when we can go back! 

Kelly Nash

Kelly Nash is a Chicago-based writer, career coach, speaker and founder of Lipstick & Ink®. She also works full-time in technology as a Role Strategy and Employee Engagement Manager at Salesforce and has over 12 years of digital marketing experience. Kelly has been featured in Thrive Global, Chicago Tribune, International Association of Women, General Assembly, Salesforce, and SheFactor. She’s fueled by black coffee, sunshine, a good ink pen, and a bold lip.