A half-day antique and thrift loop within 30 minutes of Osceola

Hey antique fanatics! Found yourself in Osceola and looking for some antique gems? Let's go! You can start on the Osceola square, then head north for a couple small-town gems. Most shops keep shorter winter hours, so we built this route around days they’re open.

Stop 1, The Grassroots Home, Osceola

A mix of vintage finds, gifts, and seasonal home goods right off the square. Typical hours run Tue–Fri 10–5 and Sat 9–2, which makes it an easy first stop before you drive north.

Best days: Tuesday to Saturday.
Tip: If you’re building a cozy winter nook, check textiles and small lamps first. Inventory turns fast.

Stop 2, C.R.O.S.S. Ministries Thrift Store, Osceola

Stretch your budget at this community thrift spot on N Main. Posted hours are Mon–Sat 10–5. Expect shelves of household goods, clothing, and surprise one-offs that rotate with donations.

Best days: Weekdays for fresher racks after weekend donations.
Tip: Bring a tote. Prices are ultra friendly, and it’s easy to overfill a cart.

Stop 3, Timber View Antiques, New Virginia, about 20 minutes

A true country antique stop. The owner keeps it mostly antiques, not just vintage. It’s open by appointment or chance, so call ahead, especially in colder weather.

Best days: When you’ve confirmed an appointment.
Tip: Ask about furniture and lighting in the back rooms. Inventory is deeper than it looks.

Stop 4, Burlap & Roses at Crooked Hedge Farm, New Virginia

Occasional-market style shopping in a barn setting, with modern-farmhouse picks and refreshed vintage. Watch their page for pop-up sale weekends, or message for hours.

Best days: Pop-up weekends during the BackRoads & ByWays Junkin’ Tour or their own scheduled sales.
Tip: The long lane back to the shop is part of the charm. Follow posted signs.

Optional add-on, Hyde & Seek, Prole

If you’ve got time, continue north to Prole. Hyde & Seek posts limited hours, usually Fri 12–4, Sat 10–5, Sun 10–5. It’s packed with primitives and curated pieces. Check hours before you roll.

Best days: Friday afternoon or Saturday.
Tip: Bring measurements for shelves or hutches. Larger pieces move quickly.

Lunch, two easy choices

• Urban on the Square, Winterset, 11–3, a nice fit if you tack on Winterset stops. Good for a warm sit-down before the drive back.
• Iron Horse Neighborhood Grill, Osceola, if you’re looping back early. Reliable, close, and open for lunch.
• We've written lots of stuff on this blog about Osceola restaurants here, here  and here.
  

Seasonal extras and a bonus stop

• Covered Bridge Festival, Winterset, second full weekend in October. If your loop lands that weekend, expect vendors, demonstrations, and a parade on Sunday. Great people watching, limited parking.
• Osceola holiday season, watch for “Christmas in the Park” and downtown events as hours shift for winter.
• While you’re out, swing by Harvest Barn Marketplace just east of town for homemade fudge, beef sticks, gift boxes, and the family-friendly Fun Farm with a corn maze and hayrides on fall weekends. They’re open seasonally from early September through December with Wed–Sun hours, so check current times before you go.

Suggested half-day timeline

• 10:00, The Grassroots Home, browse for smalls and giftable finds.
• 10:45, C.R.O.S.S. Thrift, quick scan of housewares and winter coats.
• 11:30, Drive to New Virginia.
• 11:50–12:40, Timber View Antiques, appointment or chance.
• 12:50–1:20, Burlap & Roses, if it’s a pop-up weekend.
• 1:30–2:15, Lunch in Winterset at Urban on the Square, or head back to Osceola for Iron Horse. urbanonthesquare.com+1
• 2:20–3:00, Optional Hyde & Seek if it’s a Fri/Sat/Sun.
• Bonus time at Harvest Barn Marketplace for some quick holiday shopping or a treat.

“Best days” at a glance

• Tuesday–Saturday: Grassroots is open, plus most Winterset shops.
• Friday–Saturday: Adds Hyde & Seek’s limited hours.
• Pop-up weekends: Burlap & Roses occasional market, watch their feed.
• Any weekday: C.R.O.S.S. Thrift runs Mon–Sat.

Light safety and comfort tips

Roads can glaze over fast on open stretches north of town. Check conditions, keep a scraper and warm gloves in the car, and call ahead if temps drop sharply. Timber View may close during extreme cold.

Bonus links from our blog

• Check our our 48 Hours in Osceola post, your Guide to Breakfast in Osceola, and information on Trails & Lakes around here, too.