Raymond Goldfield is a life-long New Jersey resident and an avid traveler and foodie who can be usually found on the Jersey Shore during the offseason or checking out the latest seasonal flavors at The Bent Spoon in Princeton. He has been working for Only In Your State for since early 2022, where he writes for New Jersey and Iowa and edits the Mid-Atlantic region. He can also be found writing about pop culture for GeekDad. When at home, he enjoys reading comic books and is part of The Rabbitt Stew podcast team. While New Jersey is his home base, he travels regularly and has visited Virginia, Florida, Maine, Minnesota, and Canada as well as all of NJ's border states. Ultimate travel goal? Visit all the best buffets in the United States.
There is a lot to explore in Illinois, and the Land of Lincoln is the perfect place for a multi-day road trip. It’s full of natural beauty, local culture, and delicious food and wine – and this multi-day road trip in Illinois will give you a taste of the best. Spanning from the northern corner of the state to its southern tip, this epic jaunt will prove an unforgettable adventure – one that will take you to some of the most stunning waterfalls and classic wineries across the entire state.
And of course, you’re not going to want to attempt this extensive route without having some reliable places to rest and recharge, so we’ve pinpointed some of the best places to stay across the Prairie State. Illinois is a top tourist destination, and hotels know that people might want to stop and rest at any point along their route. So you’re never far away from a conveniently-located Best Western property in Illinois. Ready to get started? Your epic waterfalls-and-wineries road trip in Illinois awaits!
1. McEachran Homestead Winery
McEachran Homestead Winery, 1917 Wyman School Rd, Caledonia, IL 61011, USA
The journey begins at this small-batch winery located in historic Boone County. Their two-acre vineyard specializes in cold-climate grapes and their vintages rotate seasonally. The rustic tasting room is located in a red barn and offers cheese and other snacks to go with your wine flight. Groups of eight or more can book a full winery tour.
Many of Illinois' most charming waterfalls are located in unlikely or out-of-the-way places. This small forest in South Elgin holds one just off the bike trail, and you're likely to have this hidden gem all to yourself.
There's a lot to explore in the greater Chicago area, so if this is where you want to take a break, check out Best Western Inn of St. Charles, located only ten minutes away.
3. Acquaviva Winery
Acquaviva Winery, 47W614 IL-38, Maple Park, IL 60151, USA
When you step into this Maple Park winery, you'll be transported straight to the heart of Italy. Owned by an Italian immigrant, this old-school winery boasts a forty-acre vineyard, a large tasting room offering a flight of six wines, and a full-service restaurant offering top-tier traditional Italian cuisine. The Signature Tour experience includes a meal, wine, and a full look at the production process.
4. Worth Waterfalls
SEPA Station 4 Waterfall Park, 11600-, 11798 S Harlem Ave, Worth, IL 60482, USA
A waterfall park in the heart of Chicago? Believe it! These man-made falls in the suburb of Worth are only a short walk from the road and are located in a public park. That makes them a popular tourist destination - and it's not hard to see why. The multiple levels of cascading water are truly hypnotic.
The tallest waterfall in Matthiessen State Park, Cascade Falls is located in a massive canyon that has been carved over long-gone millennia. The falls flow freely in the spring, although there may be less water in the summer. You can see them from a stone bridge above, but getting down to the basin provides one of the most impressive views in all of Illinois.
When you're done exploring the park, you can check in at Best Western Oglesby Inn, only seven miles from the park entrance.
Heading south to the suburban village of Rochester, you'll find this unique winery. Its grapes aren't all locally grown - owner Loren Shanle imports them from all around the country and beyond to create a diverse array of wines. This may be the only place in Illinois to try wines based on New Zealand or Argentina grapes, and their tasting menu and wine garden offer a light menu of favorites including cheeses and pizza to go with your sips.
This winery is located near Springfield, where you can check into Best Western Clearlake Plaza, less than ten minutes away.
7. Bretz Wildlife Lodge and Winery
Bretz Wildlife Lodge & Winery, 15469 IL-127, Carlyle, IL 62231, USA
Easily the strangest winery in Illinois, this Carlyle institution is a full-service restaurant with an extensive wine program. Don't let the African safari lodge theme - complete with large animal replicas around the dining room - fool you. This is no standard theme restaurant, but one that takes its wine seriously.
You're headed into rural territory now, but the route still holds places to lay your head - including Best Western Plus Centralia Hotel and Suites as you head to southern Illinois.
8. Little Grand Canyon Falls
Little Grand Canyon Road, Little Grand Canyon Rd, Pomona Township, IL 62975, USA
Are you up for a hike? To get to the waterfall here, you'll head into one of the state's most interesting geographical features. Bring your hiking boots and keep your wits about you, and you'll be rewarded with a charming, cascading waterfall near a picnic area.
9. Alto Vineyards
Alto Vineyards Champaign, 4210 N Duncan Rd, Champaign, IL 61822, USA
Operating for over 35 years, this Champaign institution was one of the first vineyards planted in the state. The award-winning winery has a 5,000-foot tasting room that's become a popular spot for weddings and other celebrations, but you can show up any day for a standard tasting of their award-winning wines. If you're lucky enough to be here on Friday, it's pizza night!
It wouldn't be a waterfall road trip in Illinois without a visit to the most impressive one. Located in the sprawling Shawnee National Forest, Burden Falls towers overhead and is accessible through a simple hike through the forest. These steep slopes have been created by erosion dating back to the ice age, and today the falls sit in an impressive canyon. Go ahead and take some time to reflect at the conclusion of this epic, multi-day adventure.
Looking for one last place to check in after this epic road trip? You're not far from Best Western Saluki Inn for a well-deserved good night's sleep.
Are you excited about this fun-filled road trip in Illinois? Let us know if there are any must-visit stops that didn’t make our itinerary. Don’t forget to find the closest Best Western property near you before you head out on the road!