The Day Tripper: Madison, Indiana

A one-time rival river town adds wine and fine dining to a reputation built on great architecture.
Historic Madison

Photograph courtesy Tri Kappa Tour of Homes

In 1958, Frank Sinatra, Dean Martin, and Shirley MacClaine traveled to Madison, Indiana—perched by the Ohio River in the southern part of the state—to capture a quintessential small-town vibe for their film Some Came Running. Nearly 60 years later (if you can ignore a few stoplights and the vape store) that nostalgic feel still permeates the city and its stunning period architecture. Madison’s downtown, which was designated a National Historic Landmark District in 2006, is a charming mix of Gothic, Revival, Italianate, and Federal styles. Private citizens open their doors to the public the first weekend of October and one weekend in November and December, but Historic Madison offers tours throughout the year. There are plenty of historic homes to peruse, but the crown jewel of the city’s wealth of architectural offerings is the Lanier Mansion. Completed in 1844 by banker, lawyer, and all-around rich guy James Lanier, the apricot-colored Greek Revival manse features curved doors, 14-foot ceilings, a dizzying spiral staircase, and an original bookcase with Lanier’s own bible. Make sure to linger behind the group tour to take in the view of the Ohio River and the grounds’ precisely sheared garden from the second floor study.

Madison has a stock of family-owned restaurants bridging the gap between diner fare and modern cuisine. If you arrive early enough, grab a doughnut at Horst’s Little Bakery Haus, where Horst himself is frying up the dough. Down a beer at the Historic Broadway Hotel & Tavern, billed as the state’s oldest tavern, and munch on their house-sliced potato chips and “skinner” dip. (Just don’t ask what’s in it.) Indulge in a slice of homemade peanut butter pie at The Attic Coffee Mill & Café, or grab a bite at Hinkle’s Sandwich Shop, which has been delivering shakes and $2 burgers since 1933.

Hinkle's Sandwich Shop
Hinkle’s Sandwich Shop

Photograph courtesy Harold Lee Miller

For dinner, though, Crystal and Jules is a pleasant change of pace. The upscale spot features surprisingly adventurous dishes like grilled bone marrow and crab-stuffed flounder, in addition to the comfort of hand-rolled pasta with a bevy of creamy sauces.

The six-stop Indiana Wine Trail features three Madison wineries. Madison Vineyards, with more than 10 acres of vines, is the only one to grow grapes on site, but that doesn’t mean you should skip the others. Thomas Family Winery uses grapes from across the midwest and California to make their own European-style wine. Lanthier Winery, which opened in 1994 and ships in grapes from Michigan and the Finger Lakes region of New York, allows you to try each of their 12 wines for free. (Ask for the award-winning cherry wine with a dark chocolate Hershey’s kiss.) If you’re feeling a little wobbly afterwards, sober up in one of their intimate booths upstairs and peruse the art on display.

More To Explore

When you’ve enjoyed all the man-made beauty on Madison’s Main Street, drive a few miles west to  Clifty Falls State Park. Covering 1,519 acres, the park features 10 trails (totaling more than 14 miles) and four waterfalls, ranging from the 60-foot-tall Big and Little Clifty Falls to the 83-foot-tall Tunnel Falls.

Clifty Falls State Park
Clifty Falls State Park

Photograph courtesy Indiana Office of Tourism Development

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