Start off the trip with a HUGE experience! Located right off of Interstate 70 lies Casey, also known as 'Big Things in a Small Town.' Here you can park the car and go on a scavenger hunt for over two-dozen BIG things scattered throughout town. Eleven of these items are Guinness World Record holders, including the World's Largest Teeter-Totter and the World's Largest Mailbox.
From Casey, head south to Robinson and make sure to bring a swimsuit! Robinson's City Park has an AWESOME pool and splash pad area, complete with a pirate ship for the kiddos to play on. Once you are dried off, head to the square in Robinson for a sweet treat and some history. Robinson is the birthplace of the Heath Bar, and the Heath Museum and Confectionery is the best place to learn about this chocolate covered toffee bar - while munching on a fresh piece!
Once nightfall is near, head west to Jasper County - home to one of the few remaining drive-in movie theaters left in the southern portion of Illinois. Folks drive from counties around to watch a flick at the iconic Drive N' Theatre, located not far outside of Newton. Once the movie has finished, head south to Olney for a great night's sleep.
Begin the day with a great cup of coffee and some breakfast from an Olney staple, Ophelia's Cup. Take your food out to Miller Grove Park to dine al fresco, while watching the beloved White Squirrels of Olney scamper around!
Hit the road for a short drive west to Flora, where you will find the Little Toot Railroad located at Charley Brown Park. If there are any train lovers in your family, they are definitely going to have fun riding this 1/4 scale railroad around the park!
After the locomotive has come to a stop, head southeast to Wabash County. Just south of Mt. Carmel you will find Beall Woods State Park, a great place for families to take a hike. Beall Woods features a handful of easy and moderate trails, and this park has one of the last remaining tracts of virgin timber east of Mississippi River. Trees at Beall Woods State Park can be as tall as 12 stories, and 3 feet in diameter!
Wrap up the day with a quick drive south to Westwood Recreation in Grayville. They have plenty of camping opportunities, including cabins to rent. This western-themed venue features SO many things the family will love. Westwood has plenty of playground equipment, 27 holes of mini-golf, and an electronic shooting range. Not to mention, they have great food at the Saloon on-site.
Begin the boys trip by teeing off at Stonewolf Golf Club in Fairview Heights - a Jack Nicklaus Signature Design Course. Stonewolf is one of only four courses throughout Illinois and Missouri designed by golf legend. The tees and fairways feature Zoysia grass, with bent grass greens - but there are also five sets of tees to play as easy or as difficult as you’d like.
Take a short drive north to Madison, home of World Wide Technology Raceway. When they aren't hosting NHRA, NASCAR, or INDYCAR events - WWT Raceway is also where you can find the Gateway Kartplex. This go-kart experience is an 11-turn, half-mile track with karts that can go up to 55 miles an hour!
To celebrate taking the checkered flag, make your way to Peel Wood Fired Pizza and Brewing Company in O'Fallon. Their Blood Orange Wheat is a great summer beer, along with the Double Take Blonde; and if you’re feeling adventurous, Peel has a handful of Beer Cocktails to try. If you're hungry, be sure to try some of their famous pizza and proscuitto involtini.
For a little post-dinner entertainment - take a short drive south to GCS Ballpark in Sauget. Enjoy a Gateway Grizzlies baseball game, and order the 'Best Burger in Baseball' - which is a cheeseburger served with a donut as the bun!
Once the game is finished, head south to Columbia to get some shut-eye before another full day of fun!
Book an early tee time for one of the best public courses in the entire state. Annbriar Golf Course in Waterloo is consistently ranked as one of the top ten public golf courses in the entire state, matter of fact, it was named the number one public golf course in Illinois for 2020! It is a beautiful, hilly course on 226 acres of land that was once a family farm. While the golf is great, the kindness and courtesy of the course staff is even better. This one is definitely one of the highlights of the trip!
After a great round of golf, it's time to try some amazing beverages. The Southern Illinois Beer Trail runs through Waterloo, which is home to two craft breweries. Hopskeller Brewing Company and Stubborn German Brewing Company sit about a block away from each other - but they offer different brews that keep people coming back for more.
To taste a few more different brews, continue working your way south on the Southern Illinois Beer Trail. The next stop is Lieferbrau Brewery in Red Bud, which is one of the more impressive venues on the route as the building was built in 1888 and has since been beautifully restored and renovated. The outdoor beer garden at Lieferbrau is the perfect place to spend an hour sipping one of their 12 varieties of beer, including their Double Crop Cream Ale – a fan favorite. Not a far drive southeast of Red Bud, you’ll find White Rooster Farmhouse Brewery in Sparta. Here you can enjoy one of several unique brews – some of which are collaborations with other breweries. One of their more unique offerings is a Belgian dark ale brewed with cinnamon and raisin bread! From there, get some rest before the final day of the trip.
Kick off the day with a fun round of trapshooting at the World Shooting and Recreational Complex in Sparta, home to the longest trapshooting line in the world! The WSRC also has Cowboy Action Shooting, Skeet Shooting, and Sporting Clays to experience as well. From there, head east to Tamaroa for a challenging round of golf at Red Hawk Golf Course. This 18-hole par 70 course has plenty of water hazards, including the 18th – which has a pond between the tee box and the green, so good luck out there! Once you’re finished golfing, head south to Du Quoin for a round of drinks and delicious food at St. Nicholas Brewing Company in Du Quoin. With an ever-changing lineup of craft beers, St. Nicks has just the drink for any guy on the trip. Have fun out there!
One of the best ways to start out a ladies trip is to catch up and unwind with glass of wine...right? Head to Crooked Creek Winery Downtown in Centralia and get a bottle of anything from traditional white wine to rosé. Of course, make sure to get a bottle or two for the road!
From there, head a few blocks away to the Centralia Carillon, one of the largest bell towers in the world. There are concerts here each weekend complete with food vendors and of course, great music!
After the concert is finished, take a drive west to Carlyle and wrap up the night at your own lakeside cottage. Hazlet Cottages at Carlyle Lake provides amazing views of the largest man-made lake in the state, and they offer many of the same amenities that you would have at home!
Begin the day with a plethora of options at Carlyle Lake! You can take some time out to go to the beach, or gather the ladies and take a beautiful walk around the lake. There are plenty of walking, biking, and hiking trails to explore the outdoors at Carlyle Lake.
Once you've freshened up, it's time to hit the Carlyle Lake Wine Trail! Begin at Bretz Wildlife Lodge and Winery - just a stones throw from the lake. There are nearly 20 wines to choose from, including fruit wines; and if some food is necessary - they have a GREAT menu.
Continuing to our next stop along the wine trail - some fantastic vino awaits your palate at Twelve Oaks Winery. Located not far outside of Carlyle, Twelve Oaks boasts award-winning wines that took home 13 medals in the 2020 Illinois State Fair Wine Competition! They were also just one of nine total Governors Cup winners in the entire state for their Chambourcin Rosé. Definitely plan to take a bottle (or four) home with you!
For an amazing dinner after the wineries, look no further than Popeye's Chop House in St. Rose. Indulge in everything from skillet mushrooms to seafood and prime rib at this hidden gem in Clinton County.
To wrap up the night, head to Hidden Lake Winery in Aviston for a wonderful experience in your own cabin! Each cabin comes with complimentary breakfast, and if you're not ready to call it a night quite yet - their tasting room is open until midnight on the weekends.
Start the day off with a little shopping in Lebanon! Whether you're looking for jewelry or antiques, there are several boutiques full of goods to catch your eye.
From there, head northeast to Highland - home of some AMAZING food. Head downtown and check out Patty Cake's - a winner of Food Network's Cupcake Wars. Also downtown you will find The Chocolate Affair, which is full of everything from truffles to hand-dipped chocolate covered Oreos. You can take a seat at the pavilion on the square and enjoy your goodies near Highland's beautiful water fountain.
Travel east on Interstate 70 to Pocahontas (Home of country music singer Gretchen Wilson), for some amazing antique shopping. There are a handful of antique shops scattered throughout town, so there's a high likelihood that you won't leave empty handed! Once you're all shopped out, head to Copper Dock Winery in Pocahontas for a drink or two on their lovely double-decker patio that overlooks a lake.
A short drive on I-70 from Pocahontas will lead you to Greenville, which has several hotels to rest your head for the night. Enjoy your trip, ladies!
Hit the MetroBikeLink Trail in Belleville for nice 9-mile bike ride to get the day started off right. This paved trail follows the MetroLink transit system and provides a great ride from the west side of Belleville to the east side of town.
To quench your thirst after the bike ride, head to The Weingarten in Belleville to have a few drinks outside on their patio area!
A very short drive east from The Weingarten you'll find Eckert's Country Store and Farm. It's very easy to spend a few hours here picking fresh fruit in the orchard, shopping in their General Store, grabbing a bite to eat at their restaurant, and indulging in some ice cream from their Custard Shop!
One attraction you will not want to miss while in Belleville is the National Shrine of Our Lady of the Snows. The Shrine provides a great opportunity to walk the grounds and experience several sacred spaces. Lourdes Grotto, Shrine Circle, and the Millennium Spire are a few of the unique, eye-catching attractions that draw folks from all across the country!
When nightfall is near, make the trip to Skyview Drive-In Theater in Belleville. Skyview is one of the few remaining drive-in movie theaters in southern Illinois, and it has been apart of Belleville since 1949! There are currently two screens that show double features each weekend.
After the movies are finished, head to one of O'Fallon's amazing hotels for a great night's sleep.
Wake up early for a bike ride on another fantastic trail! The Madison County Transit Goshen Trail has a trailhead in O'Fallon that runs north to Troy. Make a round trip, and be sure to visit the Vine Street Market at O'Fallon Station. This is one of the premier farmers markets in southern Illinois, attracting folks from miles around each Saturday from May through October!
From O'Fallon, make your way south to Columbia for a wide variety of drinks at Stumpy's Sprits Distillery. This farm to table distillery is known for it's award winning small-batch bourbon, vodka, and more. Definitely be sure to take home a bottle of your favorite Stumpy's spirits so that you can enjoy it later!
Red Bud is our next stop, which is home to The Pour Vineyard. Situated in the middle of a six-acre vineyard overlooking a large lake and rolling farmland, The Pour is a great spot for couples to relax and sip on some wine. There is indoor seating in the tasting room and outdoor seating near the lake, so there are plenty of options to enjoy yourself.
From Red Bud head southeast to Prairie du Rocher to experience an interesting piece of history. Be in awe of Fort de Chartres, which is home to the oldest building in the state. While much of this property has been rebuilt over time, the powder magazine is still the original structure built in 1720! Walk around and learn about the 300 year old French fortification - and be sure to take lots of pictures.
Finish up the trip with a drive north to Maeystown, another piece of unique history. You'll be charmed by this little village - which is one of the only communities in the state to be listed on the National Register of Historic Places in its entirety. As soon as you cross the brick bridge into town and witness the original architecture - you'll see why Maeystown is considered a hidden gem in our region. Call it a night at the Corner George Inn Bed and Breakfast to wrap up your couples trip!