We suggest planning a cozy winter. There’s something about traveling during December that makes small, real-life Hallmark movie towns shine perfectly bright. Twinkling lights, cozy meals, historic inns, and moments that make you slow down and embrace a busy holiday season. 

From a storybook bed & breakfast to a luminary-lined downtown and afternoon tea, this itinerary is perfect for anyone craving a festive Midwest escape.

We experienced this hosted winter getaway firsthand, and all opinions are our own. Please read our full disclosure policy here. 

A Cozy Winter Getaway in McHenry County

Use this itinerary to plan your very own cozy winter getaway in McHenry County. It will for sure put you into the Christmas spirit. Take care of your shopping while enjoying local experiences, from great restaurants to activities. This cozy winter getaway through McHenry County, Illinois, blends all our favorites- local flavors and drinks, along with local experiences, with a festive charm that is just perfect for the Christmas season.

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Where to Stay: Cherry Tree Inn B & B (Woodstock, IL)

The first time we stayed here, we knew this historic Inn would be a dream at Christmas time. We weren’t wrong!

Our winter retreat began at Cherry Tree Inn B & B, a restored Victorian home. From the moment we arrived, the inn felt like Christmas morning- warm, welcoming, and filled with details everywhere you look.

Each room has its own personality, and mornings start with a homemade breakfast that feels indulgent. Ours was even customized to be vegan, and it was incredible. In winter, the inn becomes especially cozy, making it the ideal home base for exploring Woodstock and nearby towns in McHenry County.

Why it’s perfect in winter: fireplaces, historic charm, and the quintessential B&B coziness. We even had a tree in our bedroom! 

Strolling Woodstock Square; Hallmark Movie Energy

If Woodstock Square looks familiar, it’s because it often feels like a movie set- and in winter, that feeling is amplified. The historic courthouse anchors the square, surrounded by independent shops, cafes, and decked out in seasonal decor from Thanksgiving to the New Year.

Bundle up and wander! Pop into local boutiques, grab a warm drink, and take in the festive storefronts. Woodstock Square is the kind of place where time slows down, especially during the holidays. 

We recommend:  Read Between The Lynes Bookstore and Ethereal Confections.

Dinner in a Festive Setting: Squire on the Square

For dinner, we headed to Squire on the Square, where they go ALL OUT with Christmas decorations. The atmosphere is so cozy and festive. 

It’s the kind of place where you settle in, enjoy conversation, and savor a meal without rushing. Don’t forget a festive holiday-themed cocktail. 

Speaking of food, read our McHenry County Vegan Food Guide for more delicious meal ideas.

Shopping & Strolling: McHenry Riverwalk Shoppes

The next day brought us to McHenry Riverwalk Shoppes, an absolutely charming collection of locally owned shops set along the Fox River. Even in winter, the riverwalk is worth a stroll, offering peaceful views and a slower pace. 

Inside the shops, you’ll find everything from gifts to home decor- the perfect place to shop local for your Christmas gifts!

A Behind-the-Scenes Holiday Experience at Richardson Tree Farm

One of our favorite experiences of the trip was a tour of Richardson Tree Farm, a multi-generation family farm known for its Christmas trees and wreaths.

Seeing where the holiday tradition begins- rows of evergreens, behind-the-scenes stories, and learning what’s required to grow Christmas trees -adds a fun layer to the season. It’s festive and an actual Midwest experience. 

Luminaries, Lights & Local Shops: Downtown Crystal Lake

As evening approached, it was the perfect time to head to Downtown Crystal Lake for luminaries and local shopping- one of those experiences that feels magical, especially with a fresh layer of snow and decorated store fronts. 

Soft candlelights lined the streets, shops stayed open late, and the entire downtown felt warm and inviting.

This was the type of experience you think of during the holidays- LOCAL shops and lots of them. So fun to peruse and look around.

Plan to do some Crystal Lake Christmas shopping!

A fun surprise as we wrapped up our walk was a local group of carolers and a visit with Santa. So perfect and cozy.

Dinner Done Right: Duke’s Alehouse & Kitchen

Dinner in Crystal Lake brought us to Duke’s Alehouse & Kitchen, a spot known for its craft beer selection and elevated comfort food.

Casual yet polished, it’s a great option after a day of shopping and strolling. In winter, it’s especially satisfying- hearty, welcoming, and perfect for winding down the day.

We devoured the fried tofu and kim-chi sandwich, smoked white bean hummus (what was that sorcery??!!), and the veggie burger. We always appreciate a restaurant that actually makes a veggie burger. It was all so good.

You can’t go wrong with a meal from Duke’s!

A Whimsical Finish: Afternoon Tea at Casting Whimsy

No winter getaway is complete without something magical- and afternoon tea at Casting Whimsy delivered just that. We love a tea shop and have never had the opportunity to do an afternoon tea. It was lovely! 

With a beautifully curated tea service, cozy surroundings, and a touch of whimsy, it felt like stepping into a fairytale. Afternoon tea is a fantastic way to slow down, reflect, and savor the season.

Why McHenry County is Perfect for a Cozy Winter Getaway

This Christmas season getaway proves you don’t need a big city to feel the magic of the season. McHenry County, Illinois, offers:

• Walkable downtowns full of independent shops
• Festive dining at local restaurants
• Historic inns with character
• A real-life Hallmark town experience

We recommend a cozy Midwest winter escape- especially during the holidays- this corner of Illinois delivers in the most charming way!