5 Perfect Weekend Getaways Chicagoans Should Take This Fall

In 4 short days, summer will officially be over here in Chicago and all over the Northern Hemisphere.

But before you fully surrender to seasonal depression and winter hibernation, remember that the fall season in Chicago is also pretty glorious and it should be enjoyed to the fullest.

Some might even argue that fall is the best season in the Midwest – the weather is mild, the changing leaves are gorgeous and that slight nip in the air means you get to haul out your favorite boots and sweaters.

There are dozens of fantastic ways to celebrate the season right here in Chicago, but it’s also the perfect time for weekend road trips to the many small towns and cities located within a couple hours of our great city.

  1. Galena, Illinois

Drive from Chicago Loop: 3 Hours

To Do List:

  • ChestnutRide the chairlift to the top of Chestnut Mountain to get expansive views of the fall colors splashed across the beautiful rolling hills of the Mississippi River Valley. Once you’re at the top, grab alfresco lunch with a view on the huge deck of the Chestnut Mountain Resort. 
  • Do a group scooter trip with Fever River Outfitters to the Galena Cellars Vineyard, where you can take a tour, do a wine tasting and enjoy the beautiful scenery. They’ll even get you back to town in a shuttle so you can be liberal with your wine pours.


  1. Starved Rock State Park, Illinois

Drive from Chicago Loop: 5 Hours

To Do List:

  • Explore 13 miles of hiking trails and 18 canyons in this stunning state park right here in Illinois. If you head Starved Rock 2there for Fall Colors Weekend (October 17), you can take a free guided hike to see the best spots for fall foliage and learn a bit about the geology and history of the park.
  • Take a mule-drawn canal ride in nearby LaSalle, Illinois. You’ll ride a replica of an 19th century canal boat that’s pulled down the hand-dug canal at a leisurely pace by a mule walking alongside the boat.


  1. Parke County, Indiana

Drive from Chicago Loop: 3 Hours

To Do List:

  • BridgeThe Wabash River Valley has the highest concentration of old-fashioned covered bridges in the whole country, which are made even more picturesque when surrounded by the changing leaves every fall. Grab your camera and check out all 31 bridges by car or bicycle – if you go October 9-18 you can also enjoy the annual Covered Bridge Festival.
  • Stay in the only jail-turned-inn in the country! The Old Jail Inn served its true purpose from 1879 to 1998, but now features prison-themed rooms and suits complete with the original cell bars and a basement winery aptly named The Drunk Tank.


  1. Saugatuck-Douglas, Michigan

Drive from Chicago Loop: 2.5 Hours

To Do List:

  • apple pickingTake advantage of the abundance of all things apple during Michigan’s apple harvest season by visiting an apple orchard where you can pick your own fruit. Visit Crane Orchards to gather your own supply of Macintosh, Gala, Honeycrisp and many other delicious varieties (90 cents a pound), roam a classic corn maze or take a hay ride.  And don’t forget to stop by Crane’s Pie Pantry Restaurant & Winery for their fresh-from-the-orchards hard cider, wine and pies.
  • Saugatuck and Douglas are known for its pristine Lake Michigan beaches, which are the perfect setting for a sunny, Indian Summer day picnic. The area boasts several lovely beaches, but you may want to check out Oval Beach, which was named by Conde Nast Traveler Magazine as one of 25 best shorelines in the world.


  1. Warrens & North Freedom, Wisconsin

Drive from Chicago Loop: 4 Hours

To Do List:

  • CranberriesYou’ll probably be surprised to learn that central Wisconsin is actually where more than half of the country’s cranberries come from, and fall is the best time to visit to see the harvest process. On October 3 is Cranberry Harvest Day when visitors can wade out into the Wetherby Cranberry Marsh in rented hip boots, taste locally-made cranberry wine and sample all sorts of homemade seasonal treats.
  • On your way back to Chicago, stop off in North Freedom for a ride through the beautiful countryside on restored steel coach trains built over a hundred years ago, which depart from an old wooden depot that’s been there since 1894. Go the weekend of October 9 – 11 for their Autumn Colors tour or October 17-18 for a special ride to a pumpkin farm.

Although our all-too-brief summer may be drawing to a close, it’s just the start of autumn.  So, enjoy these golden fall days by taking in the beauty of the season in one of these lovely towns within  just a few hours of Chicago.

About the Author:  Jay Deratany is not only an avid travel blogger, but also the owner of The Kirby, a Saugatuck bed and breakfast housed in a historic Victorian mansion that’s bee
n lovingly and luxuriously restored.  Jay is also a practicing attorney, screenwriter and passionate human rights activist. To learn more, visit The Kirby Hotel today.

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