Go Explore Downtown

Some places invite you to slow down the moment you arrive. Crawfordsville is one of them.

Brick storefronts line walkable streets, murals brighten quiet corners, and locally owned cafés offer the kind of hospitality that makes you want to linger a little longer. In Montgomery County, a weekend escape isn’t about packed schedules or big-city bustle. It’s about strolling hand in hand through historic streets, discovering hidden shops, and sharing long dinners at places that feel warmly familiar by the time dessert arrives.

For those looking to escape the rush and reconnect somewhere charming, Crawfordsville offers the perfect small-town getaway.

Where to Stay

A Downtown Loft with Historic Character

For a stay that reflects Crawfordsville’s history and charm, book the Loft at the Ben Hur Apartment Building, a cozy downtown Airbnb tucked inside one of the city’s most recognizable historic buildings.

Located in the heart of downtown, the loft places you steps away from local restaurants, shops, and cultural landmarks. Step outside and you’re immediately part of the rhythm of Crawfordsville: the quiet hum of evening traffic, storefront windows glowing after sunset, and neighbors greeting each other along the sidewalk.

The space itself balances historic character with modern comfort, creating a relaxed home base for your weekend. Pour a glass of wine, open the windows, and enjoy the feeling of being tucked into a classic Midwestern downtown.

Friday: Arrive & Unwind

Saturday: Explore the Heart of Crawfordsville

Saturday Morning

Breakfast & Downtown Discoveries

A longtime local favorite, Barefoot Restaurant & Bar is known for hearty breakfast classics and friendly service. Plates arrive stacked with comforting staples—eggs, pancakes, sizzling bacon—and the warm, welcoming atmosphere makes it easy to settle in and start the day slowly.

After breakfast, take time to explore historic downtown Crawfordsville together.
Browse the locally owned shops that line the streets, where you’ll find everything from unique gifts to vintage treasures. Small towns excel at the joy of discovery, and Crawfordsville is no exception.

While exploring, make sure to stop at two of downtown’s most colorful landmarks—the vibrant murals located on Green Street and Main Street. These works of public art bring bursts of color to the historic district and make perfect backdrops for photos that capture the spirit of your weekend.

Next, stop into The Joshua Cup for a handcrafted coffee or latte.

Saturday Afternoon

Scenic Walks & Historic Campus Views

After lunch, enjoy a leisurely stroll through Crawfordsville. Walk along West Main Street, where historic homes and classic architecture offer a glimpse into the town’s past. Tree-lined sidewalks and quiet streets make this one of the most pleasant areas for an afternoon wander.

From there, continue on to the campus of Wabash College. Founded in 1832, Wabash College is one of the nation’s oldest liberal arts institutions, and its campus offers beautiful architecture and peaceful green spaces ideal for a quiet walk together. The historic buildings and open lawns create a timeless atmosphere that feels perfectly suited to a relaxed weekend getaway.

Small-town moments that stay with you.

The beauty of Crawfordsville lies in the little things.

A quiet morning coffee beside a fountain. A mural discovered around the corner. A dinner that stretches late into the evening because the conversation is too good to end.

Montgomery County offers something increasingly rare: space to slow down and enjoy each other’s company in a setting that feels genuine and welcoming.

Here, connection isn’t about grand gestures. It’s found in simple moments shared together in a place that feels comfortably timeless.

Whether you’re wandering historic streets, sipping coffee beside the fountain, or discovering one more hidden shop, Crawfordsville offers the kind of easygoing charm that makes you want to stay just a little longer.