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Indiana’s Main Street Magic

Small towns pack big experiences for groups traveling in the Hoosier State.

Indiana has its share of big cities with high-profile attractions. But groups traveling through the state shouldn’t overlook the travel treasures in its towns and villages.

These five small towns have done an amazing job of preserving their past through a mix of 19th century architecture, world class museums, one-of-a-kind festivals and attractions, and some of the most beautiful natural settings in the state.


Car aficionados should make a point of visiting Auburn, a self-styled classic car town. Visitors can step back in time to the era of “The Great Gatsby” at the Auburn Cord Duesenberg Automobile Museum, which features one of the most extensive collections of these cars in the world. The museum is located in the old Auburn Automobile Company building and showcases 120 cars, ranging in years from 1894 to 1999, on three levels in nine automotive-themed galleries. 

Auburn hosts an Auburn Cord Duesenberg Festival over Labor Day weekend every year that brings in connoisseurs from around the world. While there, car lovers should stop at the Early Ford V-8 Foundation Museum. Another popular stop is the National Automotive and Truck Museum, which features ’50s and ’60s muscle cars, one offs, a DeLorean and a GM Futurliner, one of only 12 made by General Motors in the ’40s for the Parade of Progress. The Parade of Progress would travel coast to coast exhibiting new cars and technology, like jet engine propulsion, telephone technology and microwaves. Younger visitors to Auburn will also enjoy the International Monster Truck Museum and Hall of Fame.

If cars aren’t your thing, groups can take a self-guided walking tour of Auburn, including the historic DeKalb County Courthouse, which has a spectacular glass dome; the E.L. Cord Estate; and the home of Morris Eckhart, whose family started the Eckhart Carriage Company in 1896. There are 44 stops on the tour. Spencerville Covered Bridge is nearby, and Sechler’s Pickles offers factory tours. Downtown Auburn has boutique shops, local restaurants, three wineries and a brewery.

Village of Nashville

Not to be confused with its more glittery cousin in Tennessee, the Village of Nashville is a historic artist colony in the Blue Hills of Brown County. There are over 200 shops, art galleries and restaurants in its downtown area, and group visitors can find everything from candy and ice cream shops to clothing boutiques, book shops, jewelry and handcrafted items. There are several studios and galleries that offer classes and workshops. The oldest shop in town, The Totem Post, which opened in 1952, is a fun stop.

The village also has beautiful public art pieces scattered around downtown and is a great jumping-off point to see Indiana’s most visited state park, Brown County State Park. The park sits on 16,000 acres and features 20 miles of tree-lined roads. Visitors love to get out into nature by hiking, mountain biking or horseback riding through the park or just driving through to take in the beautiful vistas. The park is also a popular destination in the fall, when the leaves are changing to their autumn brilliance.

The Village of Story, which was founded in 1851, was turned into Indiana’s oldest country inn, The Story Inn. It has 14 rooms and cottages and a gourmet restaurant and bar in the former general store. The bar and renovated barn now host live music and monthly comedy shows. 

For groups that love to get out into nature, the 928-foot climb to the top of nearby Browning offers amazing views.


Vincennes is home to numerous museums, including the Red Skelton Museum of American Comedy, the Indiana Military Museum and one of the largest national monuments outside of Washington, D.C., the George Rogers Clark National Historical Park. The Historical Park’s huge granite memorial sits on the site of the former British Fort Sackville, which was captured by Colonel George Rogers Clark and his army — made up of frontiersmen and Frenchmen — in 1779. The surrender of the fort marks the birth of the U.S. north of the Ohio River.

Group visitors to the monument can take docent-led tours of the site, learn about its history, watch a 30-minute video presentation and visit the gift shop. The Spirit of Vincennes Rendezvous is held over Memorial Day weekend every year and features Revolutionary War reenactments and encampments, food, booths, frontier skills demonstrations and live music.

Red Skelton Museum of American Comedy celebrates the life of one of America’s most famous comedians. Red Skelton was born in Vincennes, and the museum pays tribute to his comedic legacy on television and on the radio. The museum features interactive exhibits detailing some of Skelton’s many iconic characters, including Freddie the Freeloader, and a short film that showcases famous American comedians. Group tours are available.

Indiana Military Museum features tanks, artillery and aircraft, uniforms, captured enemy souvenirs and more from the Civil War through America’s current military engagements.

Whiting and Indiana’s South Shore

Whiting is the closest Indiana city to Chicago, sitting on the shore of Lake Michigan. Whihala Beach and Whiting Lakefront Park are best known for their spectacular views of the Chicago skyline. Groups can soak up the sun as they lounge on the beach or play in the water. The park also has walking paths, a boardwalk, fishing pier and WhoaZone, a floating obstacle course with ladders, slides, swings and an aquatic trampoline.

Whiting’s other claim to fame is the National Mascot Hall of Fame, which honors some of the most memorable characters to have ever cheered on a sports team. The museum features interactive exhibits that teach guests about what it takes to become a world-class mascot. The museum is fun for groups and children of all ages.

Visitors can hike up 192-foot-tall Mount Tom, the largest sand dune in Indiana Dunes National Park in nearby Porter. The park covers 15,000 acres of dunes, oak savannas, swamps, bogs, marshes, prairies, rivers and forests and contains 15 miles of Lake Michigan shoreline.

Whiting is also home to Pierogi Fest, one of the largest Polish festivals in the world, which takes place the last full weekend of July. The event offers a variety of foods, a beer garden, live music and a parade.

Gamblers will want to stop at Horseshoe Hammond and Ameristar Casino. Nearby Fair Oaks Farm is one of the largest agritourism sites in the state.


Groups come to Madison from across the country to visit the nation’s largest contiguous National Historic Landmark District. Nestled in the rolling hills along the Ohio River Scenic Byway, Madison has 133 blocks of historic homes and buildings. 

Many of the town’s historic homes are available for tours, including the Lanier Mansion Historic Site, an 1844 Greek Revival home, and the Shrewsbury-Windle Home. Both are National Historic Landmarks. Dr. William Hutchings’ Office and Museum preserves an authentic 19th century medical office, including medical records, surgical tools and books. 

Historic Eleutherin College was founded in 1848 by the Neil’s Creek Anti-Slavery Society. The site tells the stories of the Baptists who made it their mission to educate students regardless of gender or race, including freed and fugitive slaves, before the Civil War. The Schroeder Saddletree Factory Museum offers group tours, demonstrations and exhibits that show how the family made saddle frames, clothespins and other products in the 19th century.

Madison has several trails, including a Heritage Trail that follows the riverfront along an old railroad corridor. Clifty Falls State Park overlooks the Ohio River. It is known for its waterfalls, hiking trails and nature center. The city also has two award-winning wineries, several breweries and Mad Paddle Brewstillery, which brews its own beer and makes distilled beverages.