Winter Family Getaway: Cozy Small-Town Charm in McHenry County
Winter doesn’t have to mean staying home. If your family is craving a cozy Midwest getaway that is easy, walkable, and full of charm, Woodstock, Illinois, is a wonderful winter destination, whether you visit in December, January, or February.
Located in McHenry County, Woodstock is best known as the filming location of the movie Groundhog Day, but what families quickly discover is that the town’s appeal goes far beyond one weekend in February. With a historic town square, family-friendly attractions, and a true small-town feel, Woodstock is the kind of place that feels magical all winter long.
Why Woodstock, Illinois, Is a Great Winter Town for Families
Some destinations are built for summer crowds. Woodstock shines in winter. The town is compact, welcoming, and easy to explore with kids. No packed itineraries required. It is a great choice for families looking for a relaxed weekend instead of a go-go-go vacation. Families love Woodstock in winter because:
- The historic square is walkable, even with younger kids
- Shops, cafés, and restaurants are close together (Make a stop at Read Between the Lynes for books, coffee, and ice cream!)
- Winter events, lights, and decorations add extra charm
- There is just enough to do without feeling overwhelmed
- Movie history adds a fun storytelling element for kids
A Town With Movie Magic (Kids Love the Stories!)
Woodstock’s connection to Groundhog Day is part of what makes the town so fun to explore, even outside of the official holiday. Families can walk around town and spot filming locations, including:
- Woodstock Square
- The Opera House
- Squire on the Square
- Cherry Tree Inn Bed & Breakfast
It’s easy to turn your visit into a scavenger hunt or storytelling adventure, especially for older kids and teens who enjoy learning “behind the scenes” fun facts.
Casting Whimsy: A Cozy Tea Experience Families Will Love
Located in Woodstock, Casting Whimsy is a whimsical stop that feels tailor-made for a winter family outing. This charming tea shop creates and sells its own loose-leaf tea blends, making it a fun place for parents and kids to discover new flavors together. One of the biggest highlights for families is their Afternoon Tea experience, where guests can sip tea while enjoying homemade sandwiches, quiches, desserts, and other sweet and savory treats. Each month features a new, creative theme, keeping the experience fresh and exciting. With games available to play at the tables, Casting Whimsy encourages families to slow down, connect, and enjoy quality time together. It is a wonderful way to cozy up indoors for lunch or tea while making memories during a winter visit to Woodstock.
Squire on the Square: A Piece of Movie History
Located right on Woodstock Square, Squire on the Square is a must-stop when visiting town. While many recognize it from the movie Groundhog Day, families will quickly discover it is much more than a bar. It is a full-service restaurant serving up great food, classic favorites, milkshakes, and more, making it an easy win with kids.
One of the coolest parts? The restaurant is located below the historic Woodstock courthouse, and you can actually walk through what used to be old jail cells. Learning about the building’s past and seeing the original spaces adds a fun, slightly spooky (but totally kid-friendly) layer to the experience. Kids will especially love imagining what life was like back then.
If you visit during the holiday season, the entire restaurant is decked out in festive décor, making it feel extra cozy and memorable for families.
Where to Stay with Kids: Cherry Tree Inn Bed & Breakfast
One of the best parts of visiting Woodstock in winter is staying somewhere that feels cozy, warm, and special, and Cherry Tree Inn Bed & Breakfast delivers on all of that.
This beautifully restored Victorian home is famous for its role in Groundhog Day, but families love it for much more than its movie connection. If you have ever wanted to live inside a Hallmark movie for a weekend, this is your chance. During winter, the inn feels especially magical with warm lighting, seasonal décor, and a welcoming atmosphere that instantly makes you feel at home. Some of our favorite reasons we love Cherry Tree Inn include:
- Spacious rooms that work well for parents and kids
- A comfortable, home-like environment (not overly formal)
- Homemade breakfasts that make mornings simple
- Cozy common spaces perfect for downtime
- Friendly hosts who love sharing the home’s history
Fun fact: Exes of Christmas Past and Reporting for Christmas were also filmed in this space!
Beyond Woodstock: Discover the Magic of McHenry County
While Woodstock often steals the spotlight, McHenry County as a whole is filled with small-town charm that makes it an ideal family getaway, especially during the winter months. Each community offers its own personality, local flavor, and welcoming feel.
One must-visit stop is McHenry Riverwalk Shoppes, a charming collection of locally owned boutiques tucked along the Fox River. It is the kind of place where families can stroll at an easy pace, pop into unique shops, grab a treat, and enjoy beautiful river views. Perfect for supporting local businesses while letting kids explore. They even have an ice skating ring!
Visiting during the holiday season? Richardson Tree Farm is an absolute must. Families can sip hot cocoa, pick out a Christmas tree or wreath, hop on a tractor ride, and soak in the festive atmosphere that feels straight out of a holiday movie.
No trip to McHenry County is complete without spending time in Downtown Crystal Lake, where you can shop, dine, and enjoy walkable streets full of character. Looking for a dinner spot the whole family will love? Duke’s Alehouse & Kitchen is a standout, offering incredible locally sourced food, creative craft drinks, and a warm, welcoming environment that makes it easy to enjoy a great meal together.
Add McHenry County to Your Winter Road Trip List
McHenry County is not just a Groundhog Day destination, it is a winter town families can enjoy any time. It offer movie history, cozy lodging, family-friendly attractions, and charming small-town feel. It is the perfect Midwest getaway when you want something easy, memorable, and a little magical.
If your family loves winter road trips and destinations that feel straight out of a Hallmark movie, McHenry County should be on your list.
