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Fall Weekend Travel Near Chicago

Wes Walker

Wes has been a top-selling Realtor in Chicago since 1991. He has sold more than 1000 properties and over $300 Million in Chicago real estate...

Wes has been a top-selling Realtor in Chicago since 1991. He has sold more than 1000 properties and over $300 Million in Chicago real estate...

Oct 29 3 minutes read

Are you looking to take a mini vacation and enjoy the gorgeous fall colors? Then look no further! Curbed Chicago recently highlighted a few small towns near Chicago that are a must visit and I wanted to share a few of my favorites with you! 

1. St Charles

Take a stroll down the streets of St Charles with it's grand brick buildings that line the waterfront. European influences and charm are abundant like its local forest preserve's Fabyan Windmill, built by German craftsman in the 1850's.  For a fall treat, be sure to stop by during the town's Scarecrow Festival, which draws crowds for far and wide. 


2. Chesterton

This small town sits along the Indian Dunes State Park and features tons of natural beauty. Take a hike in around the Dunes which can reach a height of over 200 feet. After your hike, you'll find rest and relaxation in a number of stylish hotels, restaurants, and activities. 


3. Woodstock

Movie lovers may fall for this town North West of Chicago. The main square with beautiful gazebo brought Woodstock it's 15 minutes of fame in the Bill Murrey film, Groundhog Day. Enjoy brick streets and old buildings that have countless stories within their walls. For example, the town's opera house opened in 1890 and housed city government offices, a public library, horses for the fire department and the Red Cross during WWII. Why not add your story to the town with a visit with friends or family?


4. Lake Geneva

Historic homes surround this lake and the 26-mile Shore Path that circles it is perfect for your own up-close tour of the area's mansions. Must see properties are Stone Manor, the largest historic home on the lake, and Wrigley Estates, a collection of properties built by the Wrigley chewing gum empire. 


5. Ottawa

Surrounded by nature, you'll find plenty of options for exploration. Only 15 minutes from Starved Rock State Park there is an abundance of hiking trails, stunning views, and waterfalls. Relax along the Fox and Illinois Rivers or take in the history of the mansions and statues highlighting where Abraham Lincoln and Stephen Douglas held their first debate. 



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