The best trips in retirement aren’t the ones packed with early museum opens and back-to-back itineraries. They’re the ones where you find a good view, take your time over a meal, and stumble into something you didn’t plan.
Dearborn County, Indiana, sitting along the Ohio River just 20 minutes west of Cincinnati, is that kind of place. Historic architecture, a six-mile riverside trail, a Victorian mansion museum, two excellent wineries, live music, and enough good restaurants to anchor every meal of the weekend. It’s relaxed without being quiet, and it earns the drive.
Book your room at the DoubleTree by Hilton Lawrenceburg—riverfront, recently renovated, and the kind of hotel where the view from your room starts doing the work the moment you check in.
Day 1: Arrive and Settle In
Get in early enough to walk. The Dearborn Trail runs along the Ohio River for six miles between Lawrenceburg and Aurora. It’s paved, flat, and best seen at golden hour. The River Cities Bike Share has rental stations along the waterfront if you’d rather ride. If birdwatching is your thing, the Oxbow Nature Conservancy, a 1,600-acre floodplain preserve where the Great Miami meets the Ohio, hosts over 270 documented species. Birdwatching or not, this is a beautiful place outdoors to spend a full morning!
For dinner, Third & Main in Aurora is the right first-night choice. Excellent steaks, a thoughtful wine list, and a historic building on the riverfront. Unhurried service and worth every bit of it.
Day 2: History, Wine, and an Evening Out
Start the Morning at Hillforest in Aurora: Drive eight minutes east to Aurora and spend the morning at your own pace. Start with coffee at Spire Book & Coffee Co. on Third Street, then walk up to the Hillforest Victorian House Museum. Built in 1855 by industrialist Thomas Gaff, the Italianate mansion sits above the river valley with views that justify the climb alone. The guided tour is unhurried, the house is stunning, and it’s the kind of history that actually sticks.
While you’re in Aurora, the Southeastern Indiana Art Guild Gallery on Second Street rotates work from regional artists year-round. Be sure to check if it’s open during your stay! And from May through October, the Tri-State Antique Market at the Lawrenceburg Fairgrounds draws serious collectors from across the tri-state area—a well-curated, outdoor market full of interesting finds.
Spent the Afternoon in Wine Country: Head north into the hills. Holtkamp Winery in Sunman is an estate winery sitting above a pond with a covered patio and vineyard views that make it very easy to lose track of time. They do brick-oven pizza on Fridays and weekends, which is a very good reason to stay until dinner. On the way back, The Ridge Winery has been producing award-winning wines in the area since 1990 and now pours at a tasting room in downtown Lawrenceburg.
End Your Evening in Lawrenceburg: Visit Proof 124 Table and Tavern for dinner to enjoy its delicious menu of American classics, strong array of cocktail choices, and a kitchen that earns its reputation. If Liberty Theater has something on that evening, go. It’s an intimate venue with a lineup that spans country, bluegrass, rock, and live theater—the kind of show that sounds better when you’re not in a stadium.
Day 3: A Slow Morning Before the Drive Home
Breakfast at 4 Speed on 50s Diner — classic diner fare, vintage car culture on the walls, and exactly the kind of unhurried, no-fuss morning that suits a Sunday. From there, it’s a short drive to Lawrenceburg Civic Park on the riverfront, a good place to stretch your legs and sit for a few minutes before heading home — outdoor stage, river breezes, and no reason to rush.
If it’s summer, have lunch at RiverWatch before you leave to enjoy a floating restaurant right on the Ohio River! Ending with a meal on the water is always the right call.
Getting Here
Dearborn County sits right on I-275 at the Indiana-Ohio border—about 20 minutes from downtown Cincinnati, easily drivable from Columbus, Louisville, Indianapolis, and Lexington. No flights needed. Just pack for a few days and come.
We’ll see you on the river.