Why This Historic Ohio River Town Is Perfect For Weekend Getaways

The Broadway Fountain is a centerpiece of downtown Madison, Indiana — Photo courtesy of Bernie Kasper

Perched along a scenic bend of the Ohio River near Cincinnati, Louisville, and Indianapolis, the small town of Madison, Indiana, is a slice of Americana that thrives in the modern age while keeping its soul intact. Madison is home to America's largest contiguous National Historic Landmark District, where elegant mansions and storefronts create a living museum of architectural treasures.

Yet, this picturesque hamlet is anything but a sleepy relic of the past, and people are taking notice. In 2024, Madison made a clean sweep, claiming the Indiana Chamber of Commerce's Community of the Year Award, a Great American Main Street Award, and ranking first in USA TODAY 10BEST Readers' Choice Award for Best Small Town in the Midwest.

Interested in discovering what all the buzz is about? Here's what you need to know to plan a fun getaway to this Midwest gem.

Things to do in Madison, Indiana

Madison's historic Main Street is a National Historic Landmark District — Photo courtesy of Bernie Kasper

Madison has a lot more going for it than charm. It hits all the right notes as "Indiana's Music City," with live tunes spilling out of a half-dozen venues throughout the week. You'll find wineries that pass the sommelier test and festivals that bring the Ohio River waterfront to life.

The town's pride is its 133-block historic district, which is filled with 19th century storefronts housing shops, art galleries, restaurants, and music venues. The Greek Revival and Federal-style buildings may look like the 1850s, but the craft coffee shops, chocolatier, and artisanal bakeries are very now. If you're interested in history, rifle through the many antique shops or visit the Schroeder Saddletree Factory Museum, which tells the story of American manufacturing innovation.

Although there are many historic mansions and churches throughout Madison, architecture enthusiasts should visit the Lanier Mansion, an 1844 Greek Revival masterpiece with gorgeous formal gardens, and the Shrewsbury-Windle House, which features a stunning three-story spiral staircase.

Madison, Indiana, is an Ohio River Valley town worth checking out — Photo courtesy of Brent Spry

Madison's riverfront, once a bustling port for steamboats, is now known as the Riverwalk Trail, where visitors have a front-row seat to river traffic, sunset views, strolls, bike rides, and summer concerts and festivals. During a Rockin Thunder River Tour, you can spot eagles and hear about old-timey life on the river.

Creative spirits soar during the Madison Chautauqua Festival of Art in Madison, Indiana — Photo courtesy of Laura Gardner

Summer is an ideal time to plan a trip to Madison. You'll find great live music here year-round, but in July, there's the Madison Regatta and Roostertail Music Festival. In August, foodies flock to the Madison Ribberfest BBQ & Blues, a decades-old tradition blending savory barbecue with soulful blues. Come September, there's the Unbroken Circle Music Festival and the two-day Madison Chautauqua Festival of Art, a massive juried art show with nearly 250 entries.

Minutes from downtown Madison, Indiana, Clifty Falls State Park is home to hiking trails and stunning waterfalls — Photo courtesy of Bernie Kasper

Outdoor enthusiasts can visit Clifty Falls State Park, just minutes from downtown. The park features 70-foot gorges, hiking trails, and impressive waterfalls. Big Oaks National Wildlife Refuge offers bird-watching, wildlife viewing, and photography opportunities.

Where to eat in Madison, Indiana

The absurdly delicious Hoosier pork tenderloin sandwich is a mainstay in Madison, Indiana — Photo courtesy of Clifty Inn

Madison's food scene features everything from refined dining to comfortable classics. Shipley's Tavern, established in 1867, and Hinkle's Sandwich Shop, a fixture since 1933, feature Hoosier and Ohio River Valley staples like juicy burgers and huge pork tenderloin sandwiches. A visit to Madison Farmers Market, the oldest farmers market in Indiana, is always a fun excursion. Got a sweet tooth? Falls Restaurant at Clifty Inn, overlooking the scenic Ohio River, serves an award-winning sugar cream pie.

River Oak Chophouse rivals high-end steakhouses in any major city. Red Roaster Coffee Company crafts artisanal beverages in a converted 19th century storefront, and Horst's Little Bakery Haus nods to the Ohio River Valley's German heritage with traditional stollen and fresh donuts.

Wineries in Madison

Lanthier Winery is one of the top wineries in Indiana — Photo courtesy of Leigh Davis

Three wineries have put Madison on the wine-tasting map. Thomas Family Winery offers award-winning wines and hard ciders in a restored 1850s carriage house. Stream Cliff Farm Winery, located on Indiana's oldest herb farm, combines wine tasting with stunning gardens and a farm-to-table cafe. Lanthier Winery, one of the top wineries in the state, charms visitors with its courtyard garden, complimentary wine tastings, and annual holiday events.

Hotels in Madison, Indiana

There are a variety of stays downtown, from boutique hotels to guesthouses — Photo courtesy of Visit Madison

In the heart of downtown, The Chandler Hotel had past lives as a livery stable and as a warehouse for the Madison Courier, the town’s newspaper. Bed-and-breakfast fans will appreciate the Iron Gate Inn, an 1840 Federal mansion.

The Fairfield Inn & Suites Madison Historic Eagle Cotton Mill was once a cotton mill and is now listed on the National Register of Historic Places and is a Historic Hotels of America member. For something more intimate, it's worth looking into guesthouses like Stablemaster's Quarters and 2nd Street Carriage House & Inn.