Romantic Mchenry County, Getaway in Illinois

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McHenry County, Illinois is only an hour northwest from Chicago (along the WI border) and there’s plenty to do for a day trip or even a long weekend Illinois getaway for couples and families. We’ve been there a few times in different seasons and now we have a fantastic round-up of some of our favorite places to visit!

Woodstock, IL

Have you seen the movie Groundhog Day? We stayed in the actual house where Phil kept waking up, day after day!! Most of the movie was filmed in this town!

Cherry Tree Inn (@cherrytreeinnbnb) is a beautiful and charming B&B located in the heart of Woodstock, Illinois. It’s exactly how you might imagine – warm, cozy, and nostalgic! We stayed in the Magnolia Room, which has the iconic movie view from the sitting area in the bay window. Every guest room has a copy of the Groundhog Day movie which is such a cute touch! I wouldn’t expect anything less of Lori, one of the owners, who was born to host. And she makes the kind of breakfast that the whole town talks about.

Cherry Tree Inn is available for events and you can even rent the whole house for a large group vacation. They also accept walk-ins on most days if you just want to peek your head in and take a look around!

A short walk from the B&B is the charming Victorian Woodstock Square Historic District  full of locally owned businesses to enjoy. We’ve been to the Woodstock Farmers Market (@woodstockfarmersmkt), recurring weekly on Saturdays until Oct. 29, 2022, and we loved that it was full of artisans and local entrepreneurs.

We highly recommend doing the self guided Groundhog Day Walking Tour. You get to see all of the memorable locations from the movie. Be sure to see the historic Woodstock Opera House! 

Another spot you HAVE to visit is Ethereal Confections (@EtherealConfections), a craft chocolate shop and cafe with a surprise! We had a swanky evening of live music at the “hidden” speakeasy, Emerson & Oliver. It has such an authentic vibe with dim lighting, traditional decor and classic cocktails. And yes, you need to find the secret password to get in! 10/10 recommend for a romantic date spot. It was a HUGE highlight for us!

If you’re heading to the area this fall, we recommend checking out Oktoberfest running September 16-17, 2022 at Kishwaukee Brewing Co. 

The annual Groundhog Days event runs Feb. 1-5, 2023 and offers official walking tours, movie screenings, trivia, pub crawls, and other themed activities.

Crystal Lake, IL

Crystal Lake is about 10 miles southeast of Woodstock and has SO much to do! Let’s start with the quaint downtown area with lots of cute local shops! One of our favorites was Out of the Box, a cute home decor and gift shop. The Downtown Crystal Lake Farmers Market occurs weekly on Saturdays until Sept 24, 2022. There’s also a Farmers Market at the historical Dole mansion that occurs weekly on Sundays until October 30, 2022.

If you’re a fan of craft beer, Crystal Lake Brewing should be on your list! They have award winning beer (it’s SO good!) and a massive tasting room. We got an up close look into their brewing process and learned how they achieve perfectly brewed beer that competes against top German breweries.

Crystal Lake Brewing

For sweet treats, head over to @julieannsfrozencustard for amazing frozen custard! They have several parking spots dedicated to their “Car Hop” orders. You just order online, text them your name & parking space and they bring it out to you!

Just a short drive from there is @QuarryCablePark where we enjoyed a drink, watched their cable wakeboarding on the lake, and just took in the scene. It’s such a cool spot. Definitely check it out! They also have sand volleyball and food! Their Oktoberfest will be held September 16-17, 2022!


The Richmond Brat Haus has the best brats! They have a ton of different toppings you can order, plus we hear the Colossal Bavarian pretzel is a must order. They were sold out when we went so we got the loaded cheese curds and they were delicious!

Spring Grove, IL – Richardson Adventure Farm

Richardson Adventure Farm Corn Maze 2022 (photo from their website)

If you’ve never been to Richardson Adventure Farm, you’re in for a real treat. It’s massive and it’s a ton of fun! In the fall, they are known for having the “world’s largest corn maze” and this year, it’s James Bond themed and amazing! The Sunflower fields will hopefully open September 10, 2022. During pumpkin season at Richardson Adventure Farm, you can also ride a carousel, go zip lining (among various other fun activities), and grab concessions like donuts, funnel cakes, hot chocolate, and spiced cider.

In the spring at Richardson Adventure Farm, you can check out their Tulip Festival with over a half million tulips! We watched the sun set over the fields at their private lakefront, while we admired the 30 different tulip varieties. You can also picnic in the area around Richardson Lake. Bring your scissors to pick tulips!

The festival is held on 15 acres with food trucks, wine, beer, free games to play, and live music on weekends! I can’t help but suggest it as a perfect outdoor adventure day date or family fun.

Harvard, IL

We had such a sweet apple picking date at Royal Oak Farm Orchard in Harvard, IL. Between their kids area (with train ride, petting zoo, and a carousel), 30 varieties of apples, pumpkin patch, country kitchen, and gift shop, you could make an entire day trip!

Royal Oak Farm Orchard

We highly recommend checking out McHenry County for a day or even a long weekend getaway! We can’t wait to visit again!

XO Jacquie & Ryan

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