This Charming Illinois City Is Home To A Historic Square Full Of Cute Local Shops

Step into the heart of one of Illinois' most charming cities at the historic Woodstock Square. Known for its classic Victorian architecture, vibrant community events, and tree-lined streets, this square boasts some of the best historical sites to visit in America. Also, with boutique shops, local artisans, and cafes around every corner, it is a great place to savor the American small town experience.

Originally known as Centerville before being renamed in 1845, the city of Woodstock itself is located in McHenry County, northern Illinois, about 60 miles from Chicago. You can drive there from Crystal Lake, about 9 miles away, or McHenry, which is 11 miles away. If you are flying in, you will likely land at Chicago O'Hare International Airport, which is roughly a one-hour drive away. History fans will want to know that the area was once home to the Ho Chunk, Illini, and Pottawatomie tribes. While development took off in the mid-1800s with the arrival of the railroad, it was not until 1873 that Woodstock was officially designated as a city.

Woodstock Square is a great U.S. city for history buffs to add to their bucket list, thanks to its historic landmarks and local craftsmanship. The square is surrounded by several preserved 19th-century buildings, such as the Old McHenry County Courthouse, which is located on its western boundary. Built in 1857, the courthouse was the seat of the county government and home to the sheriff's house and jail. When the county moved its offices, the building was renovated to become a number of restaurants, shops, and retail spaces. 

On the south side of Woodstock Square is the Woodstock Opera House, built in 1889 as a multi-use facility that hosted the city hall, library, and fire and police departments, as well as providing an auditorium for performances. The Opera House has seen countless plays, concerts, and public gatherings take place over the years, and you can still enjoy performances, attend community events, or check out the art exhibitions hosted there.

If you are a fan of "Groundhog Day," you'll also want to visit the bronze plaque that marks the spot where Bill Murray's Phil Connors steps into a puddle. The plaque, which reads "Bill Murray Stepped Here," can be found on Cass Street in Woodstock Square. As you stroll around the square, you can also step into local shops like the Roscoe Woodstock Antique Mall, where you will find unique collectables and souvenirs. If you love reading, make sure you stop by Read Between the Lynes bookstore. This independent bookstore offers a wide range of books, from bestsellers to unique finds.

There are plenty of other things to do in and around Woodstock aside from exploring the square, allowing visitors to enjoy Illinois while steering clear of Chicago. About 6 miles southwest of the city's downtown area is the All Seasons Orchard, a family-friendly destination that hosts over 15,000 apple trees and dozens of varieties. If you visit during the harvest season, you can go picking picking for apples and pumpkins. Make sure you taste the treats made from the produce, such as caramel apples, apple cider donuts, and other baked goods. Have you ever met alpacas? If you haven't, you should visit the Magic Meadows Alpacas, a Suri alpaca farm that is home to dozens of these friendly animals. You can feed the alpacas, explore the farm, and learn about alpaca farming in general.

About 5 miles south of Woodstock is the Pleasant Valley Conservation Area. The area features hiking trails, open fields, and bushes where you can spot different types of wildlife, including foxes and deer. If you are into hiking, try the Pleasant Valley Nature Trail, a 3-mile loop that passes through fields lined with beautiful wildflowers. After a day of outdoor activities, you can enjoy a delicious meal at one of Woodstock Square's many restaurants. For example, Squire on the Square provides hearty comfort food to locals and visitors alike. If you are craving Mexican flavors, you should stop by the Antigua Mexican Grill, where you'll find tacos, enchiladas, and different types of seafood on the menu.