Adair County, Iowa

If you’re into Old West history or just love a good outlaw story, the Jesse James Historical Site in Adair County is worth the stop. This quiet Iowa spot is where Jesse James and his gang pulled off the first train robbery in the American West back in July of 1873. They were aiming for a gold shipment rumored to be worth $75,000—but even though the gold never showed up, they still made off with over $3,000, which was no small change at the time.

Highlights:

• Site of the first train robbery in the American West
• Historic railroad route through Iowa
• Outlaw lore featuring Jesse James and his gang
• Peaceful roadside stop with historical signage

Pro Tip:

Bring a picnic and a camera—the site is quiet, scenic, and great for stretching your legs on a road trip.

Jesse James Historical Site, 1469 State Hwy 925, Adair, IA 50002

If you're looking for classic small-town fun, the Adair County Fair in Greenfield is where it’s at. Kicking off every year on the third Wednesday of July, this fair is one of the biggest events in the area—and it brings the full summer fair experience. Think live music, rodeos, tractor pulls, a demolition derby, and even a lumberjack show. It’s loud, fun, and full of energy.

Highlights:

• Live music and entertainment every night
• Rodeo, tractor pulls, demolition derby & lumberjack show
• FFA and 4-H exhibits and competitions
• Family-friendly activities and food vendors
• On-site camping available during the fair

Pro Tip:

Bring cash for food stands and local vendors—it’s quicker than card, and you’ll want to try everything fried.

Adair County Fair, 900 NE Elm St, Greenfield, IA 50849
Phone: 641-743-2856

Recommended Activities for Families

Just a couple miles outside of Greenfield, the Ken Sidey Nature Area is a peaceful, 100-acre slice of timberland that’s perfect for a relaxing hike. It’s got three miles of trails on-site, and it's named after Kenneth H. Sidey, a local newspaper columnist who used to roam these woods gathering inspiration for his “Nature Notes” back in the 1930s and ’40s.

Highlights:

• 100+ acres of scenic timberland
• Three miles of trails in the Ken Sidey area
• Part of a four-park complex with 10 miles of trails total
• Great for hiking, wildlife spotting, and peaceful getaways
• Named after local nature columnist Kenneth H. Sidey

Pro Tip:

Bring binoculars—this area’s great for spotting birds and other wildlife, especially in the early morning.

The Ken Sidey Nature Area, 2521 Lewis Ave, Greenfield, IA 50849

If you’re looking for a quiet outdoor spot with river access, the Middle River Forest Area in Adair County is a great little escape. This 38-acre park near Dexter gives you direct access to the scenic Middle River and is a starting point for the Middle River Water Trail. Whether you're into paddling, fishing, or just relaxing by the water, this spot checks a lot of boxes.

Highlights:

• Trailhead for the scenic Middle River Water Trail
• 38 acres of peaceful, forested landscape
• Walk-in primitive campsites for a true outdoor escape
• Canoeing, hiking, fishing, and wildlife spotting
• Canoe access ramp and good catfish action

Pro Tip:

Get there early if you’re paddling—this stretch of river is best enjoyed in the calm of the morning, especially if you're hoping to spot wildlife.

Middle River Forest Area - Adair County, 3234 200th Street, Dexter, IA 50070

If you’re looking for a laid-back spot that’s great for families or a quiet weekend escape, the Lake Orient Recreation Area in Adair County is a solid pick. Centered around the 24-acre Lake Orient, this park has something for just about everyone—whether you're casting a line, setting up camp, or just stretching your legs on the walking trail.

Highlights:

• 24-acre lake perfect for fishing and relaxing
• Walking trail and playground for outdoor fun
• Campsites with water and electric hookups
• Modern restrooms and shower facilities (May–September)
• Historical marker honoring Henry A. Wallace

Pro Tip:

If you're planning to camp, aim for late spring through early fall—amenities like water and showers are seasonal.

Lake Orient Recreation Area - Adair County, Orient, IA 50858

Attractions for Couples

If fresh, local food is your thing, you’ve got to check out Bridgewater Farm in Bridgewater, Iowa. This certified organic, family-run farm is all about sustainable farming and providing the community with top-quality produce, meats, and eggs. It’s small-scale, but they grow a seriously impressive variety of crops every season.

Highlights:

• Certified organic and family-operated
• Huge variety of seasonal produce and herbs
• Fresh meats and eggs also available
• Focus on sustainability and local food systems
• Great resource for healthy, farm-fresh groceries

Pro Tip:

Check their website or call ahead for what’s in season—you’ll want to snag your favorites before they’re gone!

Bridgewater Farm, 2409 Brown Ave, Bridgewater, IA 50837
Phone: 641-745-5368

Step back in time at the Greenfield Public Square Historic District, where small-town charm meets real-deal history. This downtown area in Greenfield is packed with character, featuring 43 historic buildings that date all the way back to 1856 when the town was first platted. It’s the kind of place where every brick seems to have a story.

Highlights:

• 43 historic buildings dating from 1856–1969
• Beautiful Lancaster-style public square layout
• Adair County Courthouse as the district centerpiece
• Filming location for the 1969 movie Cold Turkey
• Shops, services, and small-town charm still thriving

Pro Tip:

Visit in the morning and grab a coffee from a local café—then take your time strolling the square and checking out the courthouse architecture.

Greenfield Public Square Historic District, Public Square, Greenfield, IA
Phone: 641-743-8444

History buffs, nature lovers, and anyone who enjoys a good walk in the country will love the Henry A. Wallace Country Life Center in Orient, Iowa. This 40-acre site is the birthplace farm of Henry A. Wallace—U.S. Vice President, Secretary of Agriculture, and Secretary of Commerce.

Highlights:

• Birthplace of Vice President Henry A. Wallace
• 40 acres of gardens, prairie, and scenic walking paths
• Sculpture trail and a tranquil pond
• Restored farmhouse and on-site gift shop
• Open daily for self-guided tours

Pro Tip:

Plan your visit in the spring or early fall—milder temps make for perfect walking weather and the prairie is especially beautiful then.

Henry A. Wallace Country Life Center, 2773 290th Street, Orient, IA
Phone: 641-337-5019

Whether you're an aviation enthusiast or just into cool, vintage machines, the Iowa Aviation Museum and Hall of Fame in Greenfield is a hidden gem worth checking out. Located at the Greenfield Municipal Airport, the museum celebrates Iowa’s deep ties to aviation history and honors the locals who helped shape it.

Highlights:

• Honors notable Iowans in the Iowa Aviation Hall of Fame
• Nearly a dozen vintage civil aircraft on display
• Rare planes from the 1920s to 1940s
• Located at the Greenfield Municipal Airport
• Great for history buffs and aviation fans alike

Pro Tip:

Don’t skip the Hall of Fame section—some of the stories behind these aviators are just as impressive as the planes themselves.

Iowa Aviation Museum and Hall of Fame, 2251 Airport Rd, Greenfield, IA 50849
Phone: 641-343-7184