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Every Christmas season, I hear people asking where to go for that Hallmark holiday experience. You know. The town where all the cocoa is served in Christmas mugs with extra marshmallows, and romance is in the air.
The whole town looks like someone with too many extension cords had the time of their life, and Santa always makes an appearance. This year, I finally got to experience it myself with a visit to McHenry County for Christmas in Illinois during the most wonderful time of the year.
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If you are already planning ahead or still have time for a last-minute trip, put McHenry County on your list. It has all the small-town charm your holiday-loving heart could want and feels like one of the Midwest’s classic Christmas towns tucked into northern Illinois.
How do I know? Start with the Cherry Tree Inn. Add it to your bed-and-breakfast bucket list. This little charmer has history and the bragging rights of three movies filmed on-site. Two of them bring full Hallmark energy with romance, Christmas festivities, and that warm, familiar feeling that sneaks right under your winter coat.
There is nothing quite like watching a movie filmed in the exact spot where you are sitting cozy under a blanket. At Cherry Tree Inn, you get that experience times three. Check out Reporting for Christmas on Hulu and Exes of Christmas Past on Pluto TV. And if you’re into filming locations, read about another festive filming location here: A Christmas Story House.
Illinois has some of the best holiday events in the Midwest. Browse seasonal happenings across the state at Enjoy Illinois.
Christmas in Woodstock, Illinois
Begin your McHenry County holiday adventure in Woodstock, with downtown charm that feels straight out of your favorite Christmas movie. But before you get too far, grab your free printable travel journal to track all the details!
Explore Woodstock Square and Holiday Lights
Historic Woodstock Square is the perfect way to start your adventure. This downtown spot looks exactly like a holiday movie set. Independent shops surround a central square park, and the gazebo is the perfect place to sit with a cup of hot chocolate or snap a Christmas photo.
Once the sun sets, the twinkling lights spring to life on every tree around and in the park. Talk about magic. The whole place feels like someone whispered Hallmark three times. I set up my travel tripod for a few hands-free photos.
If you love beautiful holiday lights, you might also enjoy this list of the best Christmas lights in Michigan.
Lunch and Tea Time Treats in Woodstock
Before the lights come on, start with lunch. Keep it light at Expressly Leslie with a salad, a scoop of hummus, or a falafel sandwich before you head out shopping. If you want something more whimsical, stop at Casting Whimsy for afternoon tea.
The pastries are tiny works of art, and the tea list is longer than my holiday to-do list. I loved the Tea of the Month, Eskimo Kisses, with its perfect hint of mint. The husband-and-wife owners make a great team. She mixes the teas, and he names them. Pick up a few tea gifts and cross that hard-to-buy-for person off your holiday list.
Shopping, Santa Claus, and Holiday Cheer
Now that you are fueled up, wander the square for a little shopping. Treat yourself to something festive because if there is ever a season for self-love, this is it. You will find boutiques, a candy store, a bookstore, and plenty of pretty windows to peer into.
One of the side streets is home to the charming theatre featured in the movie Groundhog Day, a fun holiday tradition for many. A hands-free cross-body phone strap made shopping, sipping cocoa, and snapping selfies a breeze.
Opera House, Santa, and Afternoon Wandering
Between shops, stop into the Opera House to admire the Christmas trees decorated by local businesses. Each one is more creative than the next. You may walk out full of inspiration for your own holiday decor or, if you are in my stage of life where a Christmas tree at home feels like a big project with very little return, you can simply enjoy the view and let someone else do the heavy lifting. The whole scene feels like stepping into a winter wonderland.
As you wander, keep an eye out for Santa Claus. He appears around town in his pop-up Santa House and is always ready for photos, holiday music, and a little holiday spirit.
If you have time, pop into the McHenry County Visitor’s Center inside the historic Old Courthouse building for maps, event info, and tips from locals. Afterward, enjoy a stroll as the light displays begin to glow.
Dinner at Squire on the Square
When evening settles in, head downstairs to Squire on the Square for dinner. This stop on the Groundhog Day trail feels like Christmas held a decorating party and invited every ornament it owned.
The ceiling sparkles with twinkling bulbs, the lights shine from every corner, and the whole place buzzes with holiday cheer. The menu includes crowd pleasers and festive cocktail choices, including milkshakes with or without a little extra spirit. I was treated to a plate of flaming Greek cheese (Saganaki), a delightful surprise I would order again in a heartbeat.
IF YOU GO: WOODSTOCK
- Woodstock Square: 121 W Van Buren St, Woodstock, IL
- Expressly Leslie: 110 S Johnson St, Woodstock, IL
- Casting Whimsy Tea: 3028 English Prairie Rd, Spring Grove, IL
- Woodstock Opera House: 121 W Van Buren St, Woodstock, IL
- Squire on the Square: 110 N Benton St, Woodstock, IL
Christmas Shopping and Eats in McHenry, Illinois
McHenry keeps the Christmas in Illinois fun going with unique shops, tasty eats, and a storybook tree farm experience.
McHenry Riverwalk Shoppes
If you are lucky enough to spend more than a day or two in McHenry County, add the McHenry Riverwalk Shoppes to your To Do List. These ten adorable storefronts along the Riverwalk on Boone Creek serve as small-business incubators.
Owners get about 9 months to test ideas and grow their customer base before moving into a larger space. Parking is close, so you can hop in and out of each shop with very little walking. Bring a lightweight foldable tote because it is surprisingly easy to collect little treasures from each stop.
The McHenry Area Chamber of Commerce manages the shoppes and supports owners with coaching in marketing, budgeting, and all the behind-the-scenes basics. The shops wrap up at the end of December to make room for the next season’s lineup.
Lunch and Local Shopping in McHenry
After the Riverwalk Shoppes, head to Buddy’s Pizzeria for lunch. Nearby, you will also find a clothing boutique, a cozy coffee shop, and my favorite little stop, the Artisan MarketPlace, packed with handmade goods like knitted scarves, leather patches, art displays, clothing, and even small furniture pieces.
A Festive Stop at Richardson Tree Farm
If you want a true slice of Christmas charm, make time for Richardson Tree Farm in Spring Grove. Cut your own tree, warm up with complimentary hot cocoa, snack on freshly-made donuts, and wander a barn packed with wreaths, garland, and handmade bows. Richardson is also famous for the world’s biggest corn maze every autumn, but Christmas is when it really shines.
Holiday Stops at a Glance: McHenry
- McHenry Riverwalk Shoppes: 1257 N Green St, McHenry, IL
- Buddy’s Pizzeria: 1138 N Green St, McHenry, IL
- Artisan MarketPlace: 3316 Pearl St, McHenry, IL
- Richardson Tree Farm: 9407 Richardson Rd, Spring Grove, IL
Find Holiday Magic in Crystal Lake, Illinois
Crystal Lake is your perfect finale, with downtown lights, sweet treats, and a cozy eco-friendly dinner spot.
Downtown Festivities and Holiday Cheer
After you have polished off your pizza, head to nearby Crystal Lake, where downtown comes alive for the season. Check the Crystal Lake website for dates and times. You may catch carolers from nearby Encore Music Academy, a luminary night, or Christmas trees decorated by local businesses.
The giant Christmas tree in the center of downtown glows bright enough to guide even the most caffeine-deprived shopper. It feels like the great tree at the heart of a classic Christmas wonderland. For another amazing Christmas town, read all about Northern Indiana’s Lighting Up Shipshewana: A Spectacular Holiday Experience.
Stop at Cheshire Bakery for hot cocoa and one of the best croissant cinnamon rolls I have ever had. Take a look!
Dinner at Duke’s Alehouse and Kitchen
When you are ready for dinner, take a short walk or drive to Duke’s Alehouse and Kitchen. This Certified Green Restaurant focuses on sustainability, partners with local producers, and serves gourmet burgers, artisan sandwiches, hearty salads, and eco-conscious comfort foods. Their bar includes 100+ brews, Belgian ales, mocktails, and select nights of live music.
Holiday Stops at a Glance: Crystal Lake
- Crystal Lake Downtown: N Williams St & Brink St area
- Cheshire Bakery: 10 N Williams St, Crystal Lake, IL
- Duke’s Alehouse & Kitchen: 110 N Main St, Crystal Lake, IL
Tips for Visiting McHenry County During the Holiday Season
A little prep goes a long way toward keeping your holiday trip fun, cozy, and low-stress.
Before you head out to explore, here are a few quick tips. For more winter travel ideas, check out my favorite Winter Weekend Getaways in Michigan, my home state.
- Dress for Midwest winter. Layers, warm socks, and a good hat make outdoor activities and exploring more comfortable. Rechargeable hand warmers are my secret weapon.
- Check event calendars. Carolers, luminaries, and Santa visits vary by day.
- Take warm-up breaks. A cup of cocoa or coffee gives you a chance to rest and support small businesses.
Where to Stay in McHenry County for a Holiday Getaway
You will want at least one night here so you can slow down and soak in all that holiday charm.
If you plan to spend the night, the Cherry Tree Inn is a wonderful pick, especially if you love a little movie magic. If they are booked, there are plenty of great hotels and inns nearby. Use the map below to find the perfect spot.
Wrapping it all up – Final Thoughts on Experiencing Christmas in McHenry County
Now that I have been to McHenry County in December, I am not sure Christmas will ever be the same. If you are craving that Hallmark holiday vibe, this whole area delivers, and it is only an hour away from Chicago.
I loved the twinkling lights and cozy shops, not to mention the friendly faces everywhere we went. Come for the carriage rides, the tree farm experience, or just a little holiday break to treat yourself. I cannot promise a holiday romance, but I can promise you will find plenty of magic here.
This visit deserves to be recorded, so grab my free printable travel journal to take notes!
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