A Weekend in Litchfield & Hillsboro

Looking for a great weekend trip? Litchfield and Hillsboro are great places for a girls getaway, couples retreat, or a family gathering. Both are located in Montgomery County with Litchfield being a stop on the famous Route 66. With plenty of history, as well as things to do, these Illinois cities  make the perfect weekend getaway!


Ariston Cafe
This cafe is said to be the oldest cafe and in 2006 was named to the National Registry of Historic Places. It has been family owned since 1927 and currently serves a mix of Italian, Southern, and Seafood cuisines. Stop by to grab a quick bite and enjoy the history of this iconic cafe. Click here for their menu.

If you are looking for made-from-scratch home cooking, look no further than Jubelt’s Bakery and Restaurant. Try one of their homemade soups and a famous Horseshoe. They also serve up breakfast including omelets, skillets, and pancakes. Make sure to grab something from the bakery before you leave! Click here to view their menu.
Ice Cream Man
Looking to cure that sweet tooth? Stop in to Ice Cream Man (connected to Pizza Man) to check out Montgomery County’s only “olde time soda fountain”. This olde tyme ice cream parlor serves up all your favorites including malts, hand dipped ice cream and fresh waffle cones.
Looking for a challenge? Ice Cream Man offers the Headache Challenge which consists of 12 scoops of ice cream in 30 minutes. If you can do it you get it fo Free! You can even bring your own spoon!


Ooh La La Décor and More
Pick up that special one-of-a-kind piece of furniture at this boutique.
Route 66 Crafts and Collectables
There is always something different at Route 66 Crafts and Collectables because it is like a craft fair year round!
The Briar Rose
You never know what you are going to find at this consignment shop. Visit both locations to see what you can take home with you.


Lake Lou Yaeger
This gorgeous lake is 1400-acres full of fishing, boating, and hiking fun. If you are interested in boating, there are two ramps into the lake and no horsepower limit or speeding restrictions-perfect for boaters, skiers, and fisherman alike! If relaxing with a pole in your hand is more your style, visitors can try their hand at largemouth bass, white bass, crappie, blue gill, and catfish year-round. Lake Lou Yaeger also has Milnot Beach open Memorial Day through Labor Day. There is plenty to do at Lake Lou Yaeger!
Litchfield Museum and Route 66 Welcome Center
Check out the history of Route 66 and what it meant for the city of Litchfield. The museum features displays of period automobiles, local artifacts, and Mother Road nostalgia.

Forsee Vineyards
Forsee Vineyards is the perfect setting for a girls trip or a romantic getaway. As part of the Heartland Rivers Wine Trail, guests are invited to sip and sample the product while they stroll through the 6-acre vineyards. Guest get an idea of the process of making and bottling wine.
Hillsboro Country Club
Relax and unwind at this 9 hole golf course.
Skyview Drive-In
This drive-in is an original Route 66 theater and the only continuously operating drive-in on Illinois Route 66. Skyview Drive-In offers visitors to catch a movie under the stars April through October.

Bremer Sanctuary
There is plenty of wildlife to see and learn about at Bremer Sanctuary. Open year-round this sanctuary is home to deer, rabbits, wild turkey, migrating birds, and beautiful scenery.
Montgomery County Courthouse
This beautiful building stands alone but the interesting thing to see is the bronze statue of Abraham Lincoln across the street. Lincoln frequented Hillsboro before he was elected and this statue depicts Lincoln putting down his travel bag and umbrella and getting the kinks out of his back according to the sculptor Jon McClary.
Central Park
This park is home to a public swimming pool, skate park, and batting cages.
Glenn Shoals Lake
This lake offer fun while boating, skiing, canoeing, and fishing. The lake is 1250 acres and has a full-service marina.


America’s Best Value Inn
Hampton Inn
Holiday Inn  Express

For a full list of accommodations, please click here.

About the Author:

Tiffany Garavaglia is a creative energy with an analytical mind. She sees the world through design and innovation while being able to analyze results and provide relevant solutions. She is a strong planner, organizer and lover of coffee. Tiffany enjoys trying new things and learning as much as she can about today’s trends. At ILLINOISouth, she wears many hats and spends her day designing for our many partners, managing our social media channels, writing content for our website and providing knowledge to our partners and visitors through email marketing. Aside from her main duties she enjoys going to locations throughout the region to show our audiences everything ILLINOISouth has to offer. On the weekends you will find Tiffany spending time with her husband, Sam, young son, Sammy, and beagle, Jilly. She may also be cheering on the St. Louis Blues or binge-watching murder or doctor shows on Netflix.

One Comment

  1. MIELE S 5000 1 SERVICE MANUAL REPAIR February 21, 2017 at 10:05 am

    You can certainly see your expertise in the article you write.
    The sector hopes for even more passionate writers like
    you who aren’t afraid to mention how they believe. All the time follow your heart.

Leave A Comment