A WEEKEND GETAWAY IN WOODSTOCK IL

The perfect weekend getaway is when you arrive on Friday, and by Sunday are already planning your next visit! You are about to find out exactly why the picturesque town of Woodstock IL needs to be on to your list of weekend getaways! Once you arrive, you will find a charming downtown square, a craft beer trail, and plenty of outdoor soft adventures. Plus, you can stay at a famous bed and breakfast!

So, whether you’re seeking a leisurely weekend getaway or a nostalgic journey through history, Woodstock IL is for you! In this gem you’ll find all of the best soft adventures! You will see that one weekend just isn’t enough. Let’s start planning!

WHERE IS WOODSTOCK IL

Located in McHenry County, Illinois, Woodstock sits amidst the rolling hills and lush landscapes of the Midwest. Just over 50 miles northwest of Chicago, and only 20 minutes south of the Wisconsin border. With both O’Hare and Midway International airports around an hour’s drive, this charming town offers a tranquil escape while remaining conveniently accessible. Perfect for a weekend getaway!

Surrounded by picturesque farmland, woodlands, and pristine lakes, Woodstock boasts a scenic backdrop that beckons travelers to explore. Whether you’re seeking a peaceful retreat or an adventure in nature, Woodstock’s idyllic location provides the perfect setting for a memorable visit.

HISTORY OF WOODSTOCK IL

Groundhog Day Movie Memorabilia at Cherry Tree Inn

Woodstock Illinois was founded in 1844, originally being called ‘Centerville’. The name later changed to Woodstock after the town in Vermont, as that’s where many of the settlers were from. In the mid-1800’s, the Chicago & Northwestern railroad arrived, giving local farmers access to large Chicago markets. The early 1900’s brought both Emerson and Oliver Typewriter companies to town, and by 1922, nearly half the world’s typewriters were made in Woodstock. (Spot the typewriter in the photo above?)

While many of the early buildings were destroyed by fires, two Victorian architecture buildings remain in the Woodstock Square Historic District. The 1857 Old McHenry County Courthouse and the 1889 Woodstock Opera House. The Woodstock Opera House was originally built as the City Hall, Library, Auditorium, and Fire Department. The Woodstock Opera House continues to delight audiences with performances, ranging from live music to theatrical productions.

Orson Welles, actor, director and playwright, spent his youth in Woodstock, performing his first play on the Opera House stage. Woodstock was “home” to the world’s greatest crime fighter, Dick Tracy, as his creator Chester Gould lived there for 50 years. The town famously starred as Punxsutawney, PA, as the main filming site for the Bill Murray hit movie, Groundhog Day.

WHERE TO STAY IN WOODSTOCK IL

Inviting seating area at Cherry Tree Inn B&B

There may be other hotels in Woodstock IL, but the only place you need is Cherry Tree Inn B&B. Nestled in the heart of Woodstock, a charming bed and breakfast that exudes warmth and hospitality. Housed in a beautifully restored Victorian mansion, this historic inn offers guests a cozy retreat with modern amenities and personalized service. From the moment you step through the door, you’re greeted with elegant decor, plush furnishings, and a tranquil ambiance that invites relaxation. Each of the inn’s guest rooms is tastefully appointed, providing a cozy haven where you can unwind after a day of exploring.

Wake to the aroma of fresh coffee a delicious home-cooked meal. Prepared on-site and served in the B&B dining room, or enjoy outside on the wrap-around porch. Either way, it’s the perfect way to begin your day and an experience you won’t get at a hotel.

The Cherry Tree Inn B&B holds a special place in cinematic history as one of the iconic filming locations for the beloved movie “Groundhog Day.” Complete with movie memorabilia, a copy of the film in each guest’s room, and even a Groundhog Day board game! Guests staying at the Cherry Tree Inn B&B can immerse themselves in the magic of “Groundhog Day” by exploring the filming locations scattered throughout Woodstock.

TRAVEL TIP: Leave time in your itinerary to spend time relaxing around the B&B. Also, don’t skip the breakfast! They can accommodate any dietary restriction and everything is delicious

WOODSTOCK HISTORIC TOWN SQUARE

Walkable from the Cherry Tree Inn B&B, you’ll find the historic Woodstock town square. Bordered by quaint brick streets and adorned with century-old buildings, the square is a testament to the town’s rich history and enduring spirit. Lined with a delightful array of shops, boutiques, and galleries, the square offers unique finds, from artisan crafts and antiques to locally made goods and specialty foods.

In addition to its charming shops and boutiques, Woodstock’s town square is a culinary hub, boasting restaurants, cafes, and eateries to suit every palate. From cozy bistros serving up farm-to-table fare to diners dishing out classic comfort food, there’s no shortage of dining options to explore.

And for those craving a taste of local flavor, the square comes alive with the weekly farmer’s market! Where vendors showcase an abundance of fresh produce, artisanal goods, and homemade treats. Whether you’re a culinary enthusiast, history buff, or simply seeking a slice of small-town charm, Woodstock’s town square offers an enchanting destination brimming with character.

BREWERIES AROUND WOODSTOCK IL

McHenry Brewing Company in Woodstock IL — McHenry Brewing Company

Kishwaukee Brewing Co. in Woodstock IL — Kishwaukee Brewing Co.

McHenry County, Woodstock’s local county, has a great craft beer scene with an array of local breweries to explore. From intimate taprooms to sprawling brewery estates, there’s something for every beer enthusiast to savor. If you’re like us and are a sucker for a beverage trail, look no further! McHenry County has a Craft Beverage Trail complete with challenges and prizes! Be sure to include a few of these in your weekend itinerary!

Some of our favorites:

Cary Ale House & Brewing Co: Great beer selection and incredible food!
Kishwaukee Brewing: Incredible ambiance and amazing beer!
Crystal Lake Brewing: Fun place to hang out and yummy beers!

Cheers to unforgettable experiences and delicious brews in this dynamic corner of Illinois!

GET OUTDOORS

For soft adventurers, Woodstock IL, and the surrounding McHenry County offer a wealth of opportunities to connect with nature. Lace up your hiking sneakers and hit the trails at Moraine Hills State Park. Wander beside the wetlands, bike, fish, or birdwatch from a picturesque bench. One of our absolute favorite soft adventures to date was kayaking at Cary Lake at Rotary Park! Rent a kayak from Midwest Kayak Rentals and paddle the afternoon away. Afterwards, stroll along the trail around the lake.

For the perfect soft adventure day, check out McHenry County’s Best Hikes & Craft Breweries. Here you’ll find outdoor adventures paired up with a nearby brewery!