Facades of beautiful buildings in New Harmony, Indiana.

7 Romantic Small Towns In Indiana For A 3-Day Weekend

Sometimes, all you need to rekindle the romance is to get away from the mundane and go on a 3-day weekend trip to a small town. The Midwestern state of Indiana has just what you and your partner need to have a great time in its romantic small towns. By booking a trip to one of these towns, you can enjoy a tour in a buggy, stay at a mansion bed and breakfast, renew your vows in an open-air church, stroll through picturesque hills and waterfalls, or share a delicious Amish pastry. If you and your partner are planning a trip, consider these seven romantic small towns in Indiana for a 3-day weekend.

New Albany

The historic Culbertson Mansion in New Albany, Indiana. Image credit Thomas Kelley via Shutterstock
The historic Culbertson Mansion in New Albany, Indiana. Image credit Thomas Kelley via Shutterstock

New Albany makes for a lovely romantic getaway for several reasons. For one, it's right across the Ohio River from Louisville, Kentucky, making it a great hub to explore that city. Additionally, it has several beautiful places to visit and explore. You can take a romantic walk by the river on the paved Ohio River Greenway trail, which stretches to the nearby communities of Clarksville and Jeffersonville. In downtown New Albany, there are several high-end restaurants, ranging from Italian fare at Bella Roma Restaurant to cheese plates and wine at the Board and You Bistro & Wine Bar.

Sherman Minton Bridge spans the Ohio River between Louisville, Kentucky, and New Albany, Indiana. Image credit Thomas Kelley via Shutterstock
Sherman Minton Bridge spans the Ohio River between Louisville, Kentucky, and New Albany, Indiana. Image credit Thomas Kelley via Shutterstock

Couples can visit the luxurious Mansion Row area downtown and tour the Culbertson State Mansion Historic Site. This Second Empire-style mansion features 25 rooms, complete with frescoed ceilings, marble fireplaces, and chandeliers. You can also enjoy a romantic stay in the mansion row at the Pepin Mansion Historic Bed & Breakfast.

Madison

 Madison, Indiana (Credit: Evan Finch via Flickr)
Madison, Indiana (Credit: Evan Finch via Flickr)

Madison feels like you're stepping into a museum just by walking down its Main Street. It was a highly successful steamboat center in the mid-1800s, which contributed to the development of its affluent Victorian-era historic district. Couples with a passion for history can visit several of these structures, from the luxurious Lanier Mansion State Historic Site to the intriguing Schroder Saddletree Factory, which made parts for horse saddles in the 1800s.

A view from Madison, Indiana, bank of the Ohio river.
A view from Madison, Indiana, bank of the Ohio river.

Madison is also filled with romantic views both within and outside of town. For instance, Clifty Falls State Park features numerous waterfalls, and one can view the three bends of the Ohio River at The Point, located on the wooded campus of Hanover College. The Chandler Hotel is one of the most highly rated places to stay in Madison thanks to its contemporary design and comfortable rooms.

Nashville

Historic downtown in Nashville, Indiana. Image credit: Little Vignettes Photo / Shutterstock.com
Historic downtown in Nashville, Indiana. Image credit: Little Vignettes Photo / Shutterstock.com

Nashville has some of the most romantic vistas in Indiana. The hills of Brown County State Park and Yellowwood State Forest are a favorite of couples to hike. At Yellowwood State Forest, one can see the rare Yellowwood trees, while visitors can go for gentle strolls at Strahl Lake at Brown County State Park. Couples can enjoy walks in the cutesy downtown strip of Nashville, featuring boutiques, artisan shops, and art galleries.

Nashville, Indiana. Editorial Photo Credit: Little Vignettes Photo via Shutterstock.
Nashville, Indiana. Editorial Photo Credit: Little Vignettes Photo via Shutterstock.

The Brown County Art Gallery collects pieces from local artists who draw inspiration from everyday life and the surrounding landscape and environments. For spots to stay during your 3-day weekend, you have the option of staying right in the center of town at the Brown County Inn or taking the road less traveled and booking the historic Story Inn, located in the middle of the Brown County State Park. This quirky Woodside Inn has a reputation for being the World's Most Inconvenient Inn due to its location, but it is an excellent getaway from the noise!

Jasper

Jasper, Indiana, USA 5-18-25 Jasper Indiana old historic grain mill run by a water wheel, located at 160 Third Ave, Jasper, IN 47546. Editorial Photo Credit: Lost Shoe Studios Shutterstock.
Jasper, Indiana, USA 5-18-25 Jasper Indiana old historic grain mill run by a water wheel, located at 160 Third Ave, Jasper, IN 47546. Editorial Photo Credit: Lost Shoe Studios Shutterstock.

Jasper regularly tops the list of best small towns in Indiana due to its German immigrant heritage, magnificent cathedrals, and charming local hangouts. Jasper has a long history of German Catholic immigration, specifically. In 1867, Benedictine sisters established the beautiful Monastery of the Immaculate Conception in nearby Ferdinand, featuring an imposing dome and an expertly crafted interior.

People in a parade in Jasper, Indiana. Image credit Roberto Galan via Shutterstock
People in a parade in Jasper, Indiana. Image credit Roberto Galan via Shutterstock

It's a perfect place to tour and visit the brewery within it called St. Benedict's Brew Works. Within the town limits of Jasper itself, you can go for a picturesque train ride at the Spirit of Jasper Train Excursions, or go for a walk by the Patoka River at the Jasper Riverwalk. While you're in town, you can enjoy a show or ballet at the 700-seat Jasper Arts Center. During your 3-day weekend getaway, consider staying at the Winfield Wake B&B, housed within an 1880s Second French Empire-style home.

New Harmony

New Harmony, Indiana: Commercial Area in the town. Image credit Robin Zeigler via iStock.com.
New Harmony, Indiana: Commercial Area in the town. Image credit Robin Zeigler via iStock.com.

The most romantic places always have the best stories, and few places in Indiana have as interesting a story as New Harmony. A group of would-be utopians known as the Harmonists founded this town in 1814 as a spiritual paradise. They later sold it to the Owenists, a group known for crafting communities of peace, prosperity, and equality. These groups and their descendants carefully crafted open spaces that are deeply peaceful and romantic.

The Roofless Church in New Harmony, Indiana.
The Roofless Church in New Harmony, Indiana.

For example, you can get lost with your loved one in the private hedge maze called the Harmonist Labyrinth, renew wedding vows in the open-air Roofless Church, or see expertly designed sculptures and gardens at the JBO Sanctuary. The tiny town is highly walkable, with tours of its many historic places held at the Athenum, which has won many awards for the way natural light flows through the building. While you're here in New Harmony, book a stay at the 1899 Queen Anne Victorian Mansion: the AC Thomas House Bed & Breakfast Inn.

Shipshewana

Shipshewana, Indiana
Shipshewana, Indiana

Sometimes you have to get away from the noise of modern living to reconnect as a couple. The gentle town of Shipshewana provides a modest 3-day getaway that is sure to delight those who love rural vistas. With the town's large Amish community, Shipshewana has many cutesy country experiences. For example, you can get in a buggy together with Buggy Lane Tours to see the town or stop in for an Amish pastry or home-cooked meal at the Blue Gate Restaurant & Bakery.

An Amish man in a horse and buggy in Shipshewana, Indiana. Editorial credit: Dennis MacDonald via Shutterstock.com
An Amish man in a horse and buggy in Shipshewana, Indiana. Editorial credit: Dennis MacDonald via Shutterstock.com

You can also try out handmade goods from locally owned Amish cottage shops, including B Honey & Candles and B & L Woodcrafts. If you want to get away to talk, go on the paved Pumpkinvine Nature Trail, a 17-mile trail running through multiple communities and landscapes. To get the whole Shipshewana experience, try out the cute farmhouse inn called Meadows Inn Bed & Breakfast.

Winona Lake

Winona Lake. Wikimedia Commons.
Winona Lake. Wikimedia Commons.

Lake towns are among the most romantic places in the Midwest, thanks to their charming boardwalks, beaches, streams, and trails. Winona Lake has all of these in spades. You can easily take a boat out on the many creeks and streams around the lake, along with the lake itself, or you can dip your toes in by the beach as the sun sets at the Limitless Park and Splash Pad.

Beyer Home, Winona Lake Historic District, Winona Lake, IN. Wikimedia Commons.
Beyer Home, Winona Lake Historic District, Winona Lake, IN. Wikimedia Commons.

The Heritage Trail makes for a romantic stroll, offering lakeside views and sculptures that represent the town's rich history. Speaking of the lakeside, the Village at Winona is widely regarded as the premier shopping center in the city, featuring locally owned boutiques, restaurants, and other shops along the lakefront boardwalk. A few blocks away from the Village is the most highly rated bed & breakfast in town: The 1906 Queen Anne style Chestnut House.

By booking a 3-day weekend adventure in one of these Indiana small towns, you can get lost with your loved one in a variety of rich cultural experiences and beautiful locales. If you love hiking, explore the forests of Nashville or the waterfalls of Madison. If you prefer a bit more luxury, stay at one of the many mansion B&Bs or visit the mansion museums of New Albany. No matter what you're into, these small towns offer a wonderfully romantic 3-day weekend getaway for you and your partner.

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