Sing “Jack & Diane” as you tool around John Mellencamp’s hometown.
Seymour is not quite as small as it was when Indiana’s native son was a kid, but it’s still well worth a joyride. You can see Mellencamp’s boyhood home, now an Airbnb; the downtown mural dedicated to him and his emblematic hit “Small Town”; the diner where he ate back then (and, once in a while, eats now); the arts center he donated to the community; and the three schools he attended. A Hoosier through and through, today he resides near Monroe Lake and operates multiple studio spaces in the area.
Admire world-renowned architecture.
Columbus, Indiana, is known not only as the hometown of Chuck Taylor, famous for his iconic Converse sneakers. It is also a community with a deep, rich architectural heritage. From the Eero Saarinen–designed Miller House and Garden, to the Cleo Rogers Memorial Library by I.M. Pei, to Harry Weese’s First Baptist Church, the city shows off its modernist architecture crown jewels through guided tours offered by the Columbus Area Visitors Center.
506 5th St., Columbus, 812-378-2622
Marvel.
Rare fossils, illuminating exhibits, and interactive displays spanning 1.9 billion years of geological history are found at the Indiana Dinosaur Museum. Among the vast collection of life-sized sculptures and skeletons, the T. rex, a 17-foot turtle shell, and a sample of real dinosaur skin you can touch stand out as highlights. Out back, you can walk along the Midwest Continental Divide or hike to a scenic overlook of the University of Notre Dame. Oh, and the South Bend Chocolate Factory happens to be on the premises.
7102 Lincolnway West, South Bend
Embrace a legendary rivalry.
From IU football’s recent season, with its scene-stealing play, to Joe Tiller’s dominant coaching during Purdue’s heyday, the action during the Old Oaken Bucket game is a prime example of one of the best college football rivalries in the country. 2026 Old Oaken Bucket Game between the Indiana Hoosiers and the Purdue Boilermakers November 28
Stroll over a bridge to the past.
Founded in 1957, the annual Parke County Covered Bridge Festival is the largest in Indiana, drawing upward of 1.2 million visitors to the region each fall to shop, eat, and admire the idyllic collection of namesake landmarks. With 31 bridges and nine charming communities to discover, plan on spending a couple days to get the full experience.
2026 Parke County Covered Bridge Festival October 9–18
Leaf peep in Brown County.
Whether en route to Nashville or the home of the Hoosiers in Bloomington, take one of many scenic routes through Brown County. Over 300 miles of road boast all the yellow, orange, and red you could hope for on an autumn drive.
Pick pumpkins at Beasley’s Orchard.
At this sprawling family-owned orchard in Danville, the hayride is half the fun, bumping along through the farm’s acreage before dropping you off at the pumpkin patch. Peruse row after row of the fat orange gourds—some the size of beanbag chairs by the time the fall festival rolls around. Pick your prize, hoist it onto the wagon, and ride to checkout. Before you leave, take your turn at firing a pumpkin cannon. Refuel with a warm and sugary apple cider doughnut, an apple cider slushie, and a pork burger from the kids at the FFA stand.
2304 E. Main St., Danville, 317-745-4876
Attend the Heartland Film Festival.
With over 300 films and more than 100 filmmakers showcased throughout an 11-day period, the Heartland Film Festival is one of the top destinations for cinephiles. Whether it’s 2023’s smash hit Oppenheimer or the more than $60,000 rewarded to filmmakers, history is always on display at this can’t-miss event.
2026 Heartland Film Fest October 8–18, 317-464-9405
Haunt the Irvington Halloween Festival.
This 80-year festival celebrates all things fearful and frightening while hosting events such as the Halloween Ball, a blood drive, and the Spooky Organ Concert. (The musical instrument, not the body parts!) The festival culminates in a parade fit for festivalgoers of any age and scare level.
Wrangle a tenderloin as big as your head.
The origins of the pork tenderloin are widely traced to German immigrant Nick Freienstein, owner of Nick’s Kitchen. Nick’s still serves that same 1908 sandwich: hand-tenderized pork, buttermilk-soaked, breaded, and fried thin and crispy but still juicy. It sits on its requisite undersize, cushiony bun topped with the classic lettuce, tomato, onion, pickle, and mayo.
506 N. Jefferson St., Huntington, 260-356-6618
Sip a Manhattan at Red Key Tavern.
Red Key Tavern is unapologetically old Indianapolis—a neighborhood haunt that accidentally became legendary simply by refusing to change. Its signature Manhattan tastes fully grown-up: whiskey, sweet vermouth, bitters, and just enough confidence to sit quietly and mean it. And for the love of your grandmother, please mind your manners.
5170 N. College Ave., 317-283-4601
Sugarcoat it.
Unofficially recognized as the state pie, sugar cream relies on a simple recipe of sugar, flour, cream, and vanilla. In Winchester, Wick’s Restaurant & Pie Shop has baked up what is arguably the original for more than 70 years.
100 Cherry St., Winchester
Brave a St. Elmo shrimp cocktail.
Every Hoosier should take the dare at least once. The shrimp at this historic downtown restaurant are fat, fresh, and chilly—nothing dramatic there. But they are served in a puddle of sauce studded with shards of freshly grated horseradish. Add a squeeze of lemon, then brace yourself for the bite. The pungent heat hits your sinuses like a nuclear explosion. You’ll sputter. You’ll squint. You’ll reach for a water glass. You might cry a little bit. Then, almost as quickly as it hit, the burn fades. And somehow, you’ll go back for more.
127 S. Illinois St., 317-635-0636
Get your jaw around a Shapiro’s corned beef sandwich.
Don’t be discouraged by the line; customers move through the cafeteria queue quickly. That is mostly because many Shapiro’s diners already know what they want before they arrive. The corned beef sandwich is the standard order here, piled almost embarrassingly high on your carb of choice (go for the marbled rye and add a swipe of yellow mustard). The beef is salty, fatty, juicy, and generously served. If you can’t finish it in one sitting—or need the extra room for a slice of strawberry cheesecake—tuck leftovers inside a napkin to finish later.
808 S. Meridian St., 317-631-4041
Pick up a dozen Long’s donuts.
The glowing sign at the corner of 16th and Tremont streets on Indy’s west side has beckoned drivers since the Haughville bakery opened in 1955. “Hot. DO-NUTS.” You need cash to purchase a white box full of these delicate yeast rings. (The gas station ATM across the street can help if you forget.) Whether you share them with your coworkers or spirit them away to enjoy at home, Long’s marquee sweets are so irresistible, it’s hard to eat just one. So they’re always better by the dozen.
1453 N. Tremont St., 317-632-3741
2301 E. Southport Rd., 317-783-1442
Slurp a Triple XXX root beer float.
Whether it’s the famed float, an 1895 recipe paired with Glover’s Family Ice Cream in a heavy, frosty mug; numerous Food Network appearances; or the Drew Brees Breakfast Special, there is plenty to attract at Triple XXX Family Restaurant. In operation since 1929, this thirst station sits on Chauncey Hill, a prime locale for Purdue Boilermakers.
2 N. Salisbury, West Lafayette, 765-743-5373
Dig into a double at The Workingman’s Friend.
The surprisingly comprehensive menu posted on the wall behind the bar includes a pork tenderloin, bean soup, chili, a shrimp platter, and a “Diet Plate” that includes cottage cheese. But the meal of choice at this always-busy westside lunch spot is the double cheeseburger with a side of onion rings. Workingman’s burger was smashed before smashed was cool, sporting lacy edges of ground beef peeking from between the edges of a perfectly warm and squishy bun. Wash it down with a schooner of beer as cold as the hard cash you will need to pay for your order.
234 N. Belmont Ave., 317-636-2067
Revel at The Cake Bake Shop.
Book a table at the original Broad Ripple cottage or Carmel City Center’s chandelier-bedecked location to experience pure, glitter-dusted enchantment. Owner Gwendolyn Rogers has added plenty of magic touches, from twinkle lights by the bushel to a full-size swan sleigh parked in the front window for the holidays. The brand feels like a fairytale crossed with a royal wedding. Oh, but the cakes. From Gwendolyn’s Famous Earl’s Court Chocolate Cake to the Millionaire Cake, life doesn’t get any sweeter.
6515 Carrollton Ave., 317-257–2253
800 South Rangeline Rd., Carmel, 317-257–2253
