Head to Southwest Illinois for a Winter Weekend Full of Warmth and Charm

Slip away for a weekend of indie shops, warming drinks and winter cheer in southwest Illinois, where two routes and three waterways meet.

The brick streets of Alton, Illinois, lie quiet on a dreary December morning; a mist hangs over the Mississippi River town. But Post Commons, a cavernous post office-turned-coffee shop, is anything but sleepy. Holiday tunes from a live piano player float through the air. Diners sip cappuccinos while browsing the craft market in an auxiliary room. And Mrs. Claus (yes, really) sits at a table enjoying breakfast with a friend.

downtown hillsboro at night
Jennifer Silverberg

Opening a door into a hive of festivity isn't uncommon in Alton, nor in the area's surrounding communities. Nearly 40 of them pack the corner of Illinois across from St. Louis, where two famous highways—the Great River Road and Route 66—intersect the confluence of three major rivers. The towns there (familiar names might be Alton, Grafton and Edwardsville) sparkle especially brightly during the holidays.

A winter weekend here unspools like a Hallmark movie montage, stacked with warm and charming vignettes: A group of gentlemen gathering in a trendy restaurant in Edwardsville to serenade diners with Christmas carols. An opera show that ends with faux snow falling while smartly dressed singers belt out "White Christmas." Fireplaces crackling inside welcoming breweries and coffee shops. Even Alton's drive-through lights display seems like something written for a screenplay. Each year, seasoned volunteers, called the Grandpa Gang, hang millions of lights in Rock Spring Park. Admission proceeds help fund local charities.

Small-town gush aside, a vibrant cast of young and passionate individuals makes the region sing year-round. In Hillsboro (northeast of Alton), a slow yet steady resurgence has swept the historic downtown. On Main Street, you'll find the aesthetically curated Blackboard Mercantile, the effortlessly cool Gold Pan Records and the always-buzzing Black Rabbit Coffee. Capping the street is a brewery in a former opera house that also happens to have one of the state's largest bourbon selections.

opera house brewery hillsboro
Jennifer Silverberg

"About 10 years ago, Hillsboro was on the cusp of something cool," says Anthony Marcolini, cofounder of Opera House Brewing Company. "A few local developers were buying up buildings, and a group of volunteers started putting on events. Once the culture started to change, businesses started popping up and our town just kind of happened organically."

And it continues to evolve, like several of its neighboring towns. A new brewery-distillery-boutique hotel is on the horizon for Hillsboro, the vision of a local couple renovating a historic building. Their aim: To make the region a place where anyone can enjoy a visit—even Mrs. Claus.

blackboard mercantile hillsboro
Jennifer Silverberg

What to Do

Knock out your holiday shopping in any of the region's towns. Mississippi Mud Pottery in Alton makes beautiful pieces pressed with native flora. Blackboard Mercantile in Hillsboro has an ever-changing mix of home, kitchen and gift items. Hardcore Hammers sells customizable, Hillsboro-made hammers. The Gingham Buffalo in Edwardsville is as well-decorated as it is well-stocked with decor, furniture and accessories. Take a ride in an enclosed gondola on the Grafton SkyTour for a birds-eye view of Grafton and the Mississippi River. At the top, enjoy a glass of wine at Aerie's Winery before heading back down. Pere Marquette State Park has 12 miles of marked trails along river bluffs and is a great perch to spot bald eagles in winter.

cleveland-heath, edwardsville food
Jennifer Silverberg

Where to Eat

If you eat one thing in Alton, let it be the warm, rich chocolate chip Toll House pie from My Just Desserts. For savory sustenance, a two-hands-necessary Reuben from The Brown Bag Bistro satisfies cravings. Gentelin's on Broadway is a favorite for a cozy holiday steakhouse. At lively Cleveland-Heath in Edwardsville, gourmet comfort food lives alongside creative cocktails. When you're ready to imbibe, head to Grafton and book an igloo at Grafton Winery and Brewhaus overlooking the Mississippi River. You can order wine and beer flights, as well as pub food. A popular spot in Alton, Old Bakery Beer Company is known for all-organic brews, pizza Thursdays and colorfully graphic murals.

grafton winery and brewhouse
Jennifer Silverberg

Where to Stay

In downtown Alton, the site of the former Kendall-Bayle Cracker Company is now The Cracker Factory. Four lofts of varying sizes occupy the building, all with full kitchens and balconies—ideal for catching the sunset over the Mississippi River.

downtown alton mosaic street
Jennifer Silverberg

Holiday Itinerary

Visiting in December? Time your trip to one of these Christmas festivities.

Opera Edwardsville

Edwardsville's European-style opera company will perform its annual concert December 2, 2023, featuring a mix of traditional opera and holiday songs.

Christmas Wonderland

See the work of the Grandpa Gang on this drive-through lights display in Alton's Rock Spring Park. A stretch of the spectacle includes trees decorated by local businesses; visitors vote for their favorite. The show opens the day after Thanksgiving and runs through December.

Bethalto Christmas Village

Stroll through Bethalto Arboretum near Alton on selected dates (beginning Nov. 24, 2023) to peek into glass cottages filled with extravagant holiday displays. Lights, music and animation bring snowmen, Santa and other North Pole residents to life.

Interactive White Christmas

The weekend of December 8, 2023, catch the classic flick at the Wildey Theatre in Edwardsville. You'll get a bag of props to use during the movie.

Geography Lesson

Promoted as the Great Rivers and Routes region, this collection of southwest Illinois towns clusters along the Missouri line, not far from St. Louis. Some hug the Mississippi River, while others hide more inland.

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