Small towns just don’t get much prettier than Madison, which captivates with natural beauty and a thriving retro Main Street. More than 130 blocks of picture-perfect 1800s Federal-style homes, an 1870s fountain, and other architectural landmarks adorn the nation’s largest contiguous National Historic Landmark District, offering genteel backdrops for leisurely strolls and exploration.
What to do
Experience Madison as it was in the 1840s on tours of the restored Lanier Mansion State Historic Site. Photo courtesy Indiana State Museum and Historic Sites
Start with a history lesson about this Ohio River town (population around 12,000) that sits halfway between Cincinnati and Louisville. Nine houses and museums welcome guests for tours, including Lanier Mansion State Historic Site, the historic district’s crown jewel. Built in 1844 and once home to a prominent banker and railroad developer, the restored Greek Revival residence transports you to its early grandeur. Adults, $12.
Madison’s landscape, highlighted by craggy limestone bluffs and scenic river views, lends itself nicely to outdoor recreation. Get a little exercise and enjoy great panoramas on a walk or bike ride across the Milton-Madison Bridge, which connects to Kentucky.
Or hit the gorgeous hiking trails at Clifty Falls State Park, named for the waterfalls that cascade across the property’s northwest corner. Entrance fee is $7 per vehicle with Indiana license plates; $9 per vehicle for others.
For a look at Madison and the surrounding region from the water, book a 2-hour excursion with Rockin’ Thunder River Tours. From the jet boat’s deck, keep your eyes peeled for bald eagles as the crew points out natural and historic landmarks. Tickets, $89; passengers must be at least 7 years old. Longer adventures are available.
The wine industry flourishes in the area thanks to conducive growing conditions, and you can toast your trip at several spots. Sample the bounty at Lanthier Winery, Thomas Family Winery, and Stream Cliff Farm Winery, all of which pour sips in cozy tasting rooms.
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Where to shop
Occupying a building that dates to 1875, Trolley Barn Shops houses 5 stores, featuring everything from children’s clothing, plants, and candles to home goods and wellness products. Find unique collectibles from local artists at Cuckoos Roost, and shop for fun toys and gifts at McWhiggin’s Wonder Emporium, where you can also play Skee-Ball.
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Where to eat
A beloved hangout for nearby Hanover College students, Hinkle’s Sandwich Shop has been serving slider-size “Hinkleburgers” with pickles and onions since 1933. Mad Love Eat + Drink dishes up innovative American fare with flair, while The Crêperie prepares classic French favorites like baked Brie.
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Where to stay
Once a livery stable, the boutique Chandler Hotel features custom-designed suites that celebrate the history of Madison. Photo by Jeremy Gouge Photography
Clifty Inn in Clifty Falls State Park boasts lovely panoramic views of the town and river below. Rates start at $150. The boutique Chandler Hotel opened in 2023 with 5 suites in a beautifully repurposed downtown livery stable; 3 additional grand suites with kitchenettes were slated to open this spring. Rates start at $149.
Amy Lynch is a freelance writer from Indianapolis, Indiana.
Be sure to designate a driver if you plan to drink alcohol.
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