Romantic Couple Getaway Near Chicago: A Real Holiday-Movie Escape

By Angie & Jeff

December 14, 2025

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For full-disclosure to our readers, we want you to know that we were invited and hosted by Naturally McHenry County. The opinions in this post are completely our own and we were not paid to post this article.

A Holiday-Movie Escape Just Outside Chicago

You know you’ve wanted that feeling of being the star in your own cozy, romantic holiday movie before. McHenry County, Illinois just barely over 50 miles northwest of Chicago and bordering Wisconsin, is your answer!

We recently spent several days in McHenry County for our own romantic couple getaway and found a real holiday-movie escape that we’re certain you’ll enjoy too! We’re excited to share this enchanting itinerary for your visit to McHenry County to unlock your festive spirit.

Arrive in Woodstock – A Town Straight Out of a Holiday Movie, (Literally) – Day 1

Our home base for our time in McHenry County was the Cherry Tree Inn Bed and Breakfast (read our full review coming soon) which is stunning inside and out and is one of the movie sets for the beloved classic movie, Groundhog Day, and has recently had two new holiday movies filmed there, Reporting on Christmas and Exes of Christmas Past.

The Cherry Tree Inn Bed and Breakfast is the perfect place for a romantic holiday stay with lovely and plentiful holiday decorations (our room even had its own dedicated Christmas tree!), private bathrooms, and a breakfast spread that beats many restaurant offerings.

If the Cherry Tree Inn is already booked up and not available during your visit, there are several hotel options to consider, as well.

Explore Woodstock Square’s Picture-Perfect Charm

Woodstock, Illinois, where the Cherry Tree Inn is located, is the perfect first stop on the evening you arrive. The town square is quaint and charming in a way that transports you to the past. The townspeople take holiday decorating of the square seriously, too.

We had a great time stopping in the shops along the square, especially the impressive candy store, Rocketfizz. They stock candy from your childhood and candy from all around the world. We stocked up on some Canadian favorites, a familiar German brand, Kinder, a candy bar recommended by the store associate, Lion bar from England, and a new to us candy from Japan. It was a fun way to travel around the world right in the Midwest!

The historic Woodstock Opera House is stunning from the outside and hosts a parade of Christmas trees inside. Additionally, the Old Courthouse Center, just steps from the Woodstock Opera House, is a beautiful building inside and out. We visited Naturally McHenry County Visitor Center inside and perused the gingerbread display throughout the lobby.

We picked up a brochure at Naturally McHenry County Visitor Center outlining all of the Groundhog Day sites around town, and given our love of murals, we were immediately off to find the famous mural dedicated to the filming location. Next, we went to the location where the bar scene in Groundhog Day was shot which took us back to the lower level of the Old Courthouse Center to the restaurant, Squire on the Square for a wonderful dinner filled with ambiance.

Dinner at Squire on the Square

Squire on the Square is more than a restaurant during the holidays. It’s a destination. Upon walking into the place you’ll immediately start to notice that they have decorated pretty much every square inch and item in this place. They even have tiny little Santa hats on all the booze bottles! We were very impressed with the decorations and very pleased to tell you that the food here is great too.

If you get a chance to try the Avgolemono soup, we highly recommend you try it. It’s like a hidden secret that we would not have known about if our hosts had not told us about it due to the soup’s, unfamiliar to us, name. Avgolemono is a lemon chicken soup with so much flavor Jeff could not stop eating it until there was none left.

We also tried the pretzel appetizer which is about as big as your head and certainly enough to share. The pretzel dough is baked to perfection, crisp on the outside and warm and chewy on the inside.

Also, we highly recommend getting the flaming cheese which is on the menu as Saganaki. Not just delicious, it also provides a pre-dinner show as your server will light it up creating a small fireball tableside for your viewing pleasure.

Both of these appetizers went very nicely with our cocktails. We tried the two different martinis: the Sugar Cookie and the Mistletoe, which had vodka and cranberry juice. Both were delicious as well as very festive to look at. There are several different cocktails to try here as well as many over-the-top holiday shakes which you can order regular or boozy.

For entrees, we tried the Parmesan Crusted Cod with Grilled Vegetables and a Lemon White Sauce and the Crispy Chicken Wrap with Fries. The cod is one of the more expensive items on the menu, but worth the extra cost in our opinion.

Cozy Shopping and Scenic Strolls in McHenry – Day 2

After starting our morning with a filling and delicious breakfast at Cherry Tree Inn, we headed to McHenry to start the day at the McHenry Riverwalk Shoppes. The shops give business owners a chance to test their business concept in an adorable cottage style store along the McHenry Riverwalk for the better part of a year before expanding beyond the incubator program when the little cottages are all filled with new businesses once again.

We enjoyed Italian Christmas cookies from Oh My Ganache Bakery and found a few items from our Christmas shopping list at Marvin’s Toy Store. We also enjoyed a walk along the river to enjoy some of the outdoor scenery and nature-inspired globe sculptures.

Wandering Hand-in-Hand Through Downtown McHenry

After visiting the McHenry Riverwalk Shoppes we suggest you wander a few blocks away to downtown McHenry filled with additional charming shops and you can play the ‘find the fox’ scavenger hunt that we enjoyed. The Fox River runs through McHenry and local businesses have placed cement fox sculptures outside as an ode to the animal the river is named for. During our visit, we found several and enjoyed their adorable holiday decor added for the season.

You may also enjoy a stroll through the peaceful Fort McHenry Park admiring the beautifully decorated Christmas tree and the views from the gazebo in the center. There was a nice playground available as well.

Lunch at Buddyz Pizzeria

By now, you may be ready for a lunch break. Buddyz Pizzeria is a great place to enjoy delicious deep-dish Chicago style pizza that is way better than those chain Chicago places you’ve heard of. Keep in mind that Chicago deep dish pizza does take a bit longer to cook than a thin crust pizza so plan for about 30 to 40 minutes of wait time in the restaurant before eating or call ahead of time to get your order started before you arrive.

Don’t miss the viewing of the open storage for the museum which is on the basement level. We haven’t seen anything like it at any art museum we have visited in the past. There is an enormous glass enclosed room in the storage that is temperature and humidity controlled and hundreds of the paintings are mounted on slide out walls that can be pulled out for viewing or rotated into the galleries upstairs. It’s a wonderful way to be able to see the art that is currently archived.

Winter Fun at Richardson Adventure Farm & Tree Farm

After lunch, head over to Richardson’s Christmas Tree Farm (also known as Richardson Adventure Farm) and have a free wagon ride to enjoy their fields of Christmas trees available to cut yourself.

After the wagon ride, head inside for a free cup of hot chocolate and then get yourself some of the fresh made donuts here. The donuts are “oh my goodness” good and your tastebuds will be singing praises of joy! Ours sure did.

After trying Richardson’s delicious donuts, we got to visit the wreath making barn where workers are turning fresh evergreen boughs into works of art.

If you don’t get the chance to see the wreaths actually being made, you can still visit the wreath cold storage room near the donuts cafe where hundreds of fresh wreaths are available for sale. The fresh smell of pine in this room is amazing!

Richardson’s also has lots of unique handmade items for sale and can be a great place to do some holiday shopping.

Crystal Lake’s Luminary Glow and a Farm-to-Table Dinner

As evening approaches, head over to Crystal Lake’s Luminary Glow. Downtown Crystal Lake has some fun stores. We enjoyed walking through Lulu’s Wiggin Out, a funky gift shop which also specializes in wigs for all sorts of hairstyles. Marvin’s Toy Store is another fun stop where you’ll find toys that are built to last for generations.

The Cheshire Cakes bakery is a great place to stop in and indulge in a beautifully decorated treat and grab some hot chocolate to warm you up while you stroll festive downtown Crystal Lake.

We were lucky enough to hear sounds of singing during our visit and followed the sounds of these wonderful voices to find a group of carolers singing outside of Santa’s Workshop where you can go inside and have a photo and chat with Santa about your Christmas wishes. Just beyond Santa’s Workshop you’ll also find a large Christmas tree lit with hundreds of white lights which provides a great backdrop for a photo.

For dinner, head to Duke’s Ale House & Kitchen where they are making food from sustainable ingredients from local farmers and producers. For appetizers we got to try the Smoked White Bean Hummus (Angie normally doesn’t like hummus and she really liked this one.), Togarashi Fries (think Teriyaki flavor), and Garlic Parmesan Fries. All of them were fantastic.

For the mains, we had the Pan Roasted Salmon served with fried Brussel sprouts which were fresh and in season, and the housemade veggie burger. We really enjoyed our meals here.

There are several craft cocktails as well as loads of tap and bottled beers to try here listed on an extensive beer menu. And if the Rose All the Way Cocktail is on the menu when you arrive, go ahead and get it because it’s one of the most enjoyable drinks we’ve ever had.

Ending Your Getaway on a Sweet Note at Casting Whimsy Tea – Day 3

On your final morning we suggest visiting Casting Whimsy in Woodstock for a fine tea experience complete with the 3-tier trays of delish goodies prepared by co-owner Randy Aitken who we can say has some seriously good skills as a baker and chef.

Co-owner Paula Aitken is also blending all of the simply perfect loose leaf teas available for sale here and the teas are available in very cute metal tins which are great for gifts.

The peppermint scones Randy is making are far, far better than anything you’re going to find at any of those chain places. We also had macarons (as good as what we have enjoyed in France), several kinds of mini quiches, and several different mini tarts including Winter Berry and Lemon. And Randy even prepared delectable mini Beef Wellingtons for us.

All of this deliciousness is enjoyed in their absolutely adorable shop with so many hidden (and not so hidden) nods to Alice in Wonderland. The decor alone makes it worth a visit.

Casting Whimsy also offers a lunch menu, if you want a full meal. Either way, it’s a must stop.

Your Own Holiday-Movie Moment Awaits in McHenry County

From twinkling town squares and cozy dinners to fresh donuts, steaming cups of hot chocolate, and mornings that begin in a real movie-set bed and breakfast, McHenry County truly delivers that magical, slow-down-and-savor-it feeling so many of us crave during the holidays. It’s the kind of place where holding hands feels natural, conversations linger a little longer, and everyday worries fade into the background.

If you’ve been dreaming of a romantic couple getaway near Chicago that feels festive without being overwhelming—and charming without being overdone—this is it. McHenry County offers the perfect blend of nostalgia, small-town warmth, and unforgettable seasonal moments that make you feel like the stars of your own holiday movie.

Whether you’re planning a quick winter escape, celebrating something special, or simply looking for a reason to reconnect, we can’t recommend this itinerary enough. And if you want to stay somewhere that’s just as magical as the destination itself, be sure to read our full review of the Cherry Tree Inn Bed and Breakfast (coming soon) to see why it made our getaway even more memorable.

So grab your coziest scarf, cue the holiday music, and start planning your own festive escape—McHenry County, Illinois is ready to roll the cameras.

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