Jasper

Stop the car to explore Jasper, a hidden Southern Indiana gem. The beautifully restored Spirit of Jasper train located in Old Jasper near the Patoka River makes autumnal trips even more majestic with its Spirit of Autumn Ride & Dine, an 18-mile round trip winding through vibrant landscapes. During the ride, enjoy a meal catered by Schnitzelbank, a locally owned, authentic Old World German restaurant that plays to the town’s heritage. Points of interest along the journey include the Patoka River and dark woodlands.

The train’s journey culminates with a stop at the French Lick Resort and West Baden Springs Hotel. The latter is known for its massive dome, touted the eighth wonder of the world at its time of construction. The West Baden hotel features balconies overlooking the lobby/atrium. Shuttles and historic rail trolleys transport guests to the neighboring French Lick hotel for casino games, so no need to venture outside if temps drop. Indoor activities include bowling and swimming. The resort also offers horseback tours, a Pete Dye golf course on soaring high hills, and classic yard games. The nearby French Lick Winery is just a mile away.

To the southwest, Monastery Immaculate Conception (aka the Castle on the Hill) in Ferdinand is a must-see. Founded in 1867, the site is listed on the National Register of Historic Places. It was restored in the early 2000s and features an 87-foot-tall dome and 89 angels depicted in the interior. The monastery hilltop and wooded Dubois County countryside blaze with oranges, reds, and golds worthy of a gander.

Perhaps the best spot to leaf peep is the Hoosier National Forest near Jasper. It covers 200,000 picturesque acres, so get ready to lose yourself in the beauty of its rolling hills—some of which you can spot from the 110-foot-tall Hickory Ridge Lookout Tower. On clear days, you can see as far as 20 miles in every direction.

Don’t skip the Jasper Riverwalk, a scenic 2.1-mile paved pathway curving along the Patoka River. It’s a shaded, flat route perfect for anyone wanting to walk, run, or bike under a heavy tree canopy lit up with fall color. Here, you can access the Patoka River for fishing or small boat launching or take a short drive over to the nearby 8,800-acre Patoka Lake, complete with bald eagle nesting sites.

The Scenic Route

Take I-69 south past Bloomington, then connect with S.R. 37 going south to Paoli, passing Bedford and Mitchell along the way. Follow U.S. 150/S.R. 56 west through French Lick before continuing south to Jasper on U.S. 231.

New Harmony

The small town of New Harmony is a dream for architecture, garden, and art lovers. The Atheneum, a modern visitors center designed by Pritzker–winning architect Richard Meier and completed in 1979, serves as both a substantial landmark and an introduction to the town’s unique history.

The town was founded by Reverend George Rapp whose Harmonie Society erected 180 buildings along the Wabash River. Visitors can learn about his attempts at building a utopia on the Historic New Harmony walking tours, which meander through a cemetery and a brick-and-stone granary. Now, the town is perhaps best known for its two labyrinths, one with a stone grotto in the middle and another modeled after a 12th-century stone maze. Don’t miss The Roofless Church, an open-air dome with no seating that offers a place for silent reflection. Meanwhile, nearby Harmonie State Park boasts river-bluff woods that transform into stunning fall shades with seven trails perfect for a quiet stroll.

The downtown area is full of galleries and boutiques, including the New Harmony Gallery of Contemporary Art. This historic district is prime for autumn strolling and, in the spring, hosts a plein air art festival and impressive concert series. In the fall, it’s worth taking in the Community Halloween Party in the nearby Ribeyre Center.

New Harmony had the first commercial brewery in Indiana, and visitors today can carry on the tradition at Harmonie Society. Wind down in the peaceful atmosphere of New Harmony Inn, which provides a comfortable escape with simple but cozy furnishings (some rooms even come with a fireplace) and private balconies and patios overlooking a lake and lush parkland.

The Scenic Route

Greencastle

A scant 50 miles from Indianapolis, Greencastle represents an easy there-and-back-in-a-day target. Instead of zooming across on I-70, head out on U.S. Highway 40 to follow the Old National Road, setting the tone for the trip with a leisurely lead-in through Hendricks County. In Plainfield, fuel up on pancakes, omelets, or classic biscuits and gravy at the quintessentially retro Oasis Diner before ducking into Gilley’s Antique & Decorator Mall to hunt for vintage treasures.

Just shy of the Putnam County line, jog north on State Road 75 through Coatesville and North Salem past the McCloud Nature Park before continuing west on 236 to approach Greencastle from the north. A few historic points of interest—Eli Lilly opened his very first pharmacy here in 1859, and John Dillinger robbed the Central National Bank in 1933.

The neoclassical Putnam County Courthouse anchors a vibrant downtown square that boasts a thriving collection of storefronts and eateries. Known for its Italian wood-burning oven and thoughtfully vetted wine list, Bridges Craft Pizza & Wine Bar houses a lively dining room and a seasonal rooftop perch with panoramic views of the gently rolling terrain below.

Crackling with academic energy, DePauw University welcomes visitors to explore a bucolic 520-acre nature park sited in a former limestone quarry. (Cataract Falls State Recreation Area lies about 30 minutes to the south if you want a bigger hiking challenge and waterfall views.) Heading south out of town on U.S. Highway 231, keep an eye out for the colorful Greencastle Silos at the S & W Feed Center, part of the Putnam County Mural Project. And if you’re driving back on U.S. Highway 40, pop into Chandler’s Farm and Country Market to stock up on apples and pumpkins to take home.

The Scenic Route

Take U.S. 40 (Historic National Road) west through Plainfield and Stilesville. Turn north on S.R. 75 to North Salem. Follow S.R. 236 west through Roachdale, then continue on U.S. 231 south into Greencastle.