Couples Trip Itinerary

Explore with a Loved One

Enjoy a Couples Trip in ILLINOISouth!

DAY 1

Hit the MetroBikeLink Trail in Belleville for a 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!

Visit the Millenium Spire at the National Shrine of Our Lady of the Snows in Belleville

Photo Credit: @anthony_huan

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.

Catch a movie at the Skyview Drive-In

Photo Credit: @crazyandmaddi

After the movies are finished, head to one of O’Fallon’s amazing hotels for a great night’s sleep.

DAY 2

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 Spirits 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 sixacre 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.

Take some downtime at The Pour Vineyard

Photo Credit: The Pour Vineyard

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. If timed correctly, you will be lucky enough to experience one of the Annual Rendezvous events at Fort de Chartres – where you will witness amazing reenactments and other fun activities!

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! •

Enjoy a stroll through Maeystown

Photo Credit: Kacey Wolters

Tag us!

We love to see how folks enjoy their adventures in ILLINOISouth! If you experience any of these wonderful attractions and events please tag us in any photos by using the hashtag #ILSouth. You can also email your pictures to info@illinioisouth.org. We would like to use your photos in upcoming publications!

Visit ILLINOISouth.org/Road-Trip-Itineraries for more travel ideas!