Disclaimer: This post was sponsored by Madison County, Iowa Chamber & Welcome Center. All opinions and photos are mine.
If you’re seeking a relaxing weekend in a picturesque destination that evokes feelings of nostalgia, go to Madison County, Iowa.
The region is best known for its covered bridges and awe-inspiring views—towns like Winterset, St. Charles, and nearby Orient offer incredible dining, one-of-a-kind shopping, and unequaled museums.
Spending a weekend exploring Madison County will make you fall in love with it like I did.
DAY 1
LUNCH: MEMORIES ON 1ST AVENUE – TEA ROOM & TIMELESS TREASURES
One of the best places to spend your lunch hour is at Memories on 1st Avenue – Team Room & Timeless Treasures (111 S. 1st Avenue, Winterset) for a scratch-made meal in a unique setting.
We entered the cozy restaurant via a door located just below street level, and to my delight, each table was adorned with beautiful china and glassware. The owner (who doubles as the chef!) prepares sandwiches, soup, quiche, and fresh salads.
I thought the Reuben on marble rye bread, a cup of homemade Strawberry Soup, and a glass of iced raspberry tea was divine. Sharing a towering lemon meringue pie, we chatted about Winterset and the town’s history.
PRO TIP: The eatery is open Tuesday-Friday, 11 a.m.-2 p.m., with limited seating. Small groups should reserve a table in advance. Add a few minutes of extra time to your lunch to peruse the restaurant’s displayed antiques – many of which are for sale.
CITY PARK
A leisurely tour of City Park (South St and S 9th St, Winterset) must be part of your travel plans when in the area. The 76-acre natural oasis features a full-service campground, playgrounds, and historic structures to explore on foot.
A self-guided tour of Clark Tower was, by far, my favorite discovery. We traversed a narrow, one-mile road by car to the top of a curvy hill en route to it. Built in 1926 in honor of early settlers, the limestone landmark resembles something from a fairy tale.
If you’re comfortable with heights, climb the 25-foot Clark Tower for a 360-degree Middle River Valley view.
Another park feature not to be missed includes the whimsical chainsaw sculptures by Iowa artist Gary Keenan. The English Hedge Maze leads to a sundial, and an adjacent bocce ball court invites parkers to play a game.
Nearby Bennett Cabin and Cutler-Donahue Bridge, each built in the 1800s, are photo-worthy attractions.
Seek out the stone bridge for another photo moment. It’s the location where Robert and Francesca’s movie scene was filmed.
PRO TIP: Traveling with kids? Prepare to explore the park and its play features for at least an hour.
CUTLER-DONAHOE BRIDGE
Cutler-Donahoe Covered Bridge is the closest to downtown Winterset, a short drive by car. It was built in 1870 by Eli Cox (the same man who constructed the Covered Bridge House) and was moved to Winterset’s City Park in 1970.
Spanning 79 feet, the bridge is within walking distance of the road that winds through the park. You’ll appreciate the stone bridge, also nearby, the site of the movie’s film scene where Robert and Francesca enjoy a picnic.
HOLLIWELL BRIDGE
Holliwell Bridge is the longest of the six original, covered bridges at 122 feet. Built in 1880 by Harvey P. Jones and George K. Foster, it is located southeast of Winterset.
It appears in the movie The Bridges of Madison County when Francesca meets Robert there before they return to her home for dinner.
Parking is available nearby, and the path to the bridge is easy to navigate.
COVERED BRIDGES WINERY
Our visit to Covered Bridges Winery (2207 170th Trail, Winterset), four miles outside of town, was a delightful one. I hope you add to our itinerary.
We had the pleasure of sitting with winemaker Kevin Fifo to sip award-winning vino while learning how the business evolved from making wine at home to a sophisticated operation using 100% Iowa grapes.
After sampling red and white drier varieties, we ultimately bought a bottle of LaCresent 2021 (2017 Mid-American Wine Competition Silver winner) to bring home.
The tasting room offered six white, six red, and two rosé wines to select from for a multi-sample tasting experience.
Whether you drop in for a glass of wine in the tasting room or on the patio overlooking the valley, I highly recommend adding it to your itinerary. They don’t push wine on you to try, and instead serve you “whichever wine you like to drink.”
PRO TIP: A guided tour and tasting takes about two hours. If you visit during harvest, you may get to sample fresh juice from the presser. View the Facebook page for music events, weather permitting.
WINTERSET CIDERY
There must be something magical in the Iowa soil because it’s also known for producing delicious apples. In fact, the Red Delicious variety, originally named Hawkeye, was discovered in Iowa.
At Winterset Cidery (1638 Hwy 169, Winterset), apple lovers can sip hard cider from dry to sweet inside a tasting room with floor-to-ceiling orchard views. Free popcorn and available board games promise a good time.
During our visit, we chose to sit on the front porch to watch as summer rainstorm clouds developed. I sipped Lime Habanero Hard Cider, which finished sweet and sampled another favorite, John Wayne Bone Dry Hard Cider. Each one tasted crisp with authentic flavor.
PRO TIP: Check the Facebook page to plan your visit during the apple-picking season or to check for events like Thursday Trivia or live music performances.
HOGBACK BRIDGE
After enjoying a glass of wine or cider, drive southwest to Hogback Bridge (follow the signs!) on your way back to Winterset.
At 97 feet, the awe-inspiring bridge was built in 1884 and sits in its original location. The Hogback was named for the Hogback Ridge at the valley’s west end (its convex curve resembles the curve of a hog’s back).
You’ll appreciate the scenic view at this one. Like each covered bridge in the county, it was renovated in the 1990s to maintain its beauty.
CEDAR BRIDGE
You should drive to nearby Cedar Bridge while exploring Hogback Bridge since they are close in distance. The covered bridge, built in 1883, is the same bridge that appears on the cover of the book The Bridges of Madison County by Robert James Waller.
Unfortunately, the bridge fell victim to arson twice in recent years and had to be reconstructed. The replica reminds us of the sentiment shared by the movie’s characters portrayed by Clint Eastwood and Meryl Streep.
JOHN WAYNE BIRTHPLACE MUSEUM
Madison County is the site of film productions and produced a Hollywood star, John Wayne. Born Marion Robert Morrison on May 26, 1907, at home, John Wayne was the oldest boy of two to parents Clyde and Mary.
He lived in Winterset until age seven. As a boy, he walked about town with his brother and dog, Duke. Eventually taking on the nickname Duke, the family moved to California in 1914. The actor starred in 170 films.
John Wayne Birthplace & Museum (205 S. John Wayne Drive, Winterset) allows the actor’s fans to tour his childhood home and pursue film artifacts and items from his collection.
The first stop? The museum’s theater room for a short film highlighting his achievements. Next, take a self-guided tour of each of the two galleries.
I was curious about the actor’s collection of coffee mugs – he had a keepsake mug made for each movie. Handwritten letters, a car, clothing, and an address book were some of the personal items included in the collection.
PRO TIP: I recommend devoting at least an hour to touring the birthplace home and museum if you like to read each panel. Review the John Wayne In Iowa map showing the family’s moves across the state.
WINTERSET PUBLIC LIBRARY
As a writer, I feel at home in a library. We stopped at Winterset Public Library (123 N. 2nd St.) to take a relaxing break while admiring the work of young artists on display.
I was impressed to find a basket of free produce available near the checkout counter, which I assumed came from the community garden behind the library outside.
PRO TIP: Often the site of entertaining events, the library’s Facebook page is an excellent resource in preparation for your visit.
MONUMENTAL PARK
Next to the library, Monumental Park houses one of the earliest Civil War monuments in Iowa, a 14-foot marble pillar inscribed on each side. Four black cannons, gifted to Madison County in 1878, surround its base.
Modern benches with historical references were added to the park. I enjoyed learning about how George Washington Carver wandered into Winterset, where he lived and worked for two years.
MURALS & FREEDOM ROCK
The Madison County Freedom Rock (half a block east of John Wayne Birthplace and Museum) is the 64th painted rock in the state’s collection. Painted by Ray Sorenson, it showcases the Quilts of Valor Foundation headquartered in Winterset.
An art alley with interactive murals is adjacent to the Madison County Courthouse. Artists James Navarro and Katie Jensen intended visitors to discover ways to pose with the paintings.
DINNER: THE DRIFT
I can’t think of a better place to enjoy dinner after exploring Madison County than The Drift (112 N. 1st St, Winterset). The taproom serves flatbreads, sandwiches, and wraps using farm-to-table ingredients.
We shared a charcuterie board while sipping craft beers as a prelude to dinner. The Drift Salad and Roast Beef Panini served on locally sourced bread made the dining experience exceptional.
PRO TIP: If you’re not a craft beer drinker (21 Iowa beers on tap!), ask about wine and mead selections. Non-alcoholic beers are an option.
COVERED BRIDGE HOUSE
Our stay at Covered Bridge House changed my life. It made me slow down and remember that delightful moments can be as simple as enjoying a sunset and listening to cicadas buzz on a summer evening.
A restored 1908 country home turned Airbnb, the three-bedroom, two-bath home is incredibly well-maintained and modernized to accommodate couples or families seeking a weekend of solitude.
A short drive from dining, shopping, and museums in Winterset, it was perfect for us. We watched the movie The Bridges Over Madison County at night while drinking champagne in a room surrounded by antiques and framed artwork.
The charming home had every comfort we wanted, and to be honest, I loved the experience so much that I wished the house was for sale so we could buy it.
The creak of the original wood floors.The sunset view from the porch. I loved our stay, as will you.
DAY 2
BREAKFAST: THE BAKERY UNLIMITED
When everyone in town tells you to order an apple fritter at The Bakery Unlimited (119 N. John Wayne Dr., Winterset), you go. Also known for its daily specials, cracked wheat bread, and delectable bagels, the local hangout draws an early morning crowd.
DOWNTOWN SHOPPING
While I only had time to stop in some of the stores in Winterset, I discovered gems near the courthouse square and a short walk from it.
DUTCH COUNTRY GENERAL STORE
Dutch Country General Store (72 E. Court Ave., Winterset) is a retail space selling little of everything.
From fresh groceries to retro candy and sodas to home decor and toys, you’ll find something you can’t leave the store without. I purchased a scented candle, Fresh Cut Grass.
ROW YOUR GOAT
Row Your Goat (110 W. Court Ave., Winterset) is a must-visit shop specializing in Iowa-made goods and groceries. I found it hard to resist purchasing handmade soap. Their inventory of candles, artwork, framed photography, and gift items is irresistible.
BRICK ROAD BOOKS
A reader’s dream, Brick Road Books’s (105 W. Court Ave., Winterset) front retail area is stocked with new fiction and non-fiction releases, while the rear of the store contains used books.
PRO TIP: Kids get a free used book when they visit, and the monthly book club selections keep shoppers returning for new reads.
WHOMPY BEAR BOUTIQUE
Owned and operated by a mom-turned-entrepreneur, Whompy Bear Boutique (114 N. 1st Ave., Winterset) is the newest addition to Winterset’s shopping scene.
The clothing, shoes, and accessories for sale are on-trend, including the latest seasonal fashions. The inviting store features a stroller parking zone and interactive spaces for kiddos, such as a push-and-listen station (are those bees buzzing?) and a toy treasure box.
HARVEST CREEK
Harvest Creek(108 N. 1st Ave.) is unlike any other store you may have seen. The shop is filled floor-to-ceiling with antiques, oddities, home decor, candles, and more.
In preparation for fall, I noticed an abundance of witchy decor items; however, they may sell similar whimsical gifts year-round.
PINE CREEK, LTD
At Pine Creek, Ltd. (110 N. 1st Ave., Winterset), you’re likely to find a gift for yourself or someone else since the artfully decorated shop is filled with items for one’s home, from pillows and picture frames to stationary and soup mixes.
Seasonal floral picks and sit-a-bouts are arranged in vignettes throughout the store.
PRO TIP: The store’s Holiday Open House takes place in November, debuting elaborately decorated trees and decor.
MADISON COUNTY CHAMBER OF COMMERCE & WELCOME CENTER
The Madison County Chamber of Commerce & Welcome Center (73 E. Jefferson St, Winterset) is the best place to shop for a souvenir of your trip. The well-stocked shelves include artwork and photography created by locals. Additionally, the staff is eager to answer your travel questions and offer advice.
SPOONS FULL OF SUGAR
As soon as I walked into Spoons Full of Sugar (420 S. John Wayne Dr.), I wanted everything she was selling. Located a short walk from the courthouse square, the boutique carries boho-style women’s apparel, leather shoes and handbags, and chunky jewelry.
Most of the jewelry is handmade by the owner. Silver spoons are crafted into rings, necklaces, and bracelets. Shoppers in search of faith-based finds will appreciate the store’s inventory.
PRO TIP: Like what you see here but can’t make it to the shop? Visit her online store.
EVERGREEN AND LILY FLORAL STUDIO
Evergreen and Lily Floral Studio (419 S. First St., Winterset) is across the street from Spoons Full of Sugar, a worthwhile stop if you’re searching for bountiful houseplants or fresh floral arrangements.
The store is also female-owned and operated, stocking inventory created by women.
I loved how each houseplant was given a name to make the shopping experience more fun. I couldn’t leave without buying a handcrafted greeting card for our house host.
PRO TIP: Visit the Facebook page to RSVP for upcoming floral arrangement workshops.
LUNCH: MADISON COUNTY WINERY, ST. CHARLES
After a great shopping day, Madison County Winery is the only place to go (3021 St. Charles Rd., St. Charles), a 16-minute drive southeast of Winterset. You can sample and purchase Iowa-produced wines and craft beers from two local breweries.
The vineyard produces five varieties of grapes on 30 acres.
We enjoyed a five-sample tasting of wines of our choice while visiting with the owner/winemaker. I thoroughly enjoyed learning about the process of wine production from vine to glass while we enjoyed a platter of artisan cheeses, meats, and chocolates with our wine.
I appreciated the aged white cheddar with the dry Rosato red wine. Other favorites included crisp and refreshing Vignoles, semi-dry white Hunter’s Moon, and Red Cabernet.
PRO TIP: Ask for a sample of the Unfiltered Wine Rosemary & Garlic Vinegar with bread. You’ll want to buy a bottle to take home. Bonus! If you arrive during a Wood Fired Pizza event, enjoy $2 off glasses of wine.
IMES BRIDGE
Located East of St. Charles, the Imes Bridge is visible from the highway. One of the oldest of the remaining covered bridges, the 81-foot bridge was originally located closer to the town of Patterson but was moved to its current location in 1977.
The bridges were constructed with wood and designed to be covered to last longer. Some visitors, particularly couples, have carved their names or initials into the wood to signify their love.
THE FARMSTAND BY MANASTASH MERCANTILE
Like a boutique store in a big city, The Farmstand by Manastash Mercantile (101 Main St., St. Charles) caters to shoppers who want gifts for themselves or someone else with sophisticated style.
The mother-daughter duo believes “people here deserve these things, and there is something for everyone.” 
What started as a jewelry business evolved into a specialty store selling dishes, apparel, gourmet foods, fresh floral arrangements, and more.
WAYWARD SAINTS GIFT SHOP
Wayward Saints Gift Shop (located across the street from The Farmstand by Manastash Mercantile) is a cozy shop supplying locals and visitors with handcrafted items from nearly 20 regional vendors.
Wayward Saints Farm LLC produces goat milk products such as soaps, lotions, and hand-poured soy candles. You may find them at an area farmers market when they are not running the shop.
IOWA QUILT MUSEUM
If you quilt or appreciate those who do, visiting the Iowa Quilt Museum (68 E. Court Ave.) is essential.
The downstairs gallery houses evolving exhibits of handcrafted quilts. Curious about the evolution of making quilts, I walked upstairs to view historical displays.
On the day of my visit, I voted for my favorite quilt, a 3-D pattern, from the collection “Welcome Home: A Celebrate of Quilts.” It was interesting to look closely at the handiwork of quilts dating back to the 1850s.
PRO TIP: The museum installs new exhibits four times a year. Next door, Pieceworks Quilt Shop, sells fabric and supplies.
ROSEMAN BRIDGE
Do you remember the movie scene when Francesca leaves a note for Robert inviting him to dinner? This moment was filmed at Roseman Bridge southwest of Winterset, spanning the Middle River. The 1883 bridge is considered haunted by some after a jail escapee was said to have appeared and then disappeared from its roof in 1892.
PRO TIP: If you visit Friday-Sunday, stop next door at the Roseman Covered Bridge Gift Shop to purchase a souvenir commemorating your visit to the famous bridge.
PIZZA ON THE PRAIRIE: HENRY WALLACE FARM
If you’ve never experienced a farm-to-table dinner at sunset, you haven’t lived. Pizza on the Prairie at the Wallace Centers of Iowa (2773 290th St., Orient) is a reservation-only event on Friday nights from early June to late September.
Upon our arrival, we followed the path to the kitchen to order our brick oven pizzas and house-made cucumber salad. We walked with craft beers in hand to a table of friendly locals who welcomed us to sit with them.
Live folk music played as we dined on two styles of pizzas and engaged in conversation with our new friends. Inspired by the sunset, we left the table to walk a manicured path through the prairie amongst towering sunflowers and a temporary Prairie Art Exhibit.
The unique experience left an impression on us. After driving back from the event, we vowed to do two things: 1.) Learn how to make fresh tomato compote (delicious on the pizza) and 2.) Take our new friend’s advice for aging well, “Stay active and be social.”
PRO TIP: Bring lawn chairs or a picnic blanket to the event.
DAY 3
BREAKFAST: PETITE CAFE
Petite Cafe (106 W. Court Ave., Winterset) is worth driving hundreds of miles to experience. The owner, Naomi, wanted to open a coffee shop after the husband and wife team had roasted beans (@pammelparkcoffee) for years.
The popular cafe serves gorgeous, scratch-made pastries with top-quality coffee. The grab-and-go options like salads, wraps, and bakery items made with locally sourced ingredients.
People wait in line to order inside the 250-square-foot cafe (seating for 10!), and if a seat isn’t available, they eat their pastries and sip lattes from an outdoor park bench.
PRO TIP: Arrive at the cafe when they open to claim a scone before they’re gone.
DOWNTOWN MURAL TOUR
A series of murals designed by artists James Navarro and Katie Jensen create an interactive experience in an alley adjacent to courthouse square in historic downtown Winterset.
Each painted scene offers visitors something to discover. Look closely at the details to find the hidden gems.
MONTROSS PHARMACY SODA FOUNTAIN
I knew I wasn’t leaving town without a visit to Montross Pharmacy Soda Fountain (118 N. 1st Ave), and neither should you. Since 1921, the pharmacy has served the community.
Craving an old-fashioned cherry Pepsi®, I entered the store and headed to the back, where I discovered a nostalgic scene. Residents sat on bar stools and in booths, enjoying a hot breakfast and discussing the day’s events.
PAMMEL STATE PARK
You must visit Pammel State Park (1900 Pammel Park Rd) before departing from Madison County.
Only a 12-minute drive southwest of Winterset, the park is well-revered by locals for its five miles of trails, picnic areas, and historic 1858 Harmon Tunnel – the only highway tunnel in the state.
The town celebrates the park’s 100th anniversary this year.
BONUS IDEAS
BIG RACK BREW HAUS
Unfortunately, we didn’t have time to hit every go-to spot in the county otherwise, we would have made it to Big Rack Brew Haus (2475 Hiatt Apple Trail, Winterset) – just another reason to return to Madison County.
THE IOWA THEATRE
The Iowa Theatre (121 N. John Wayne Dr.) is a renovated retro movie theater that shows modern-day movies and the John Wayne Matinee Series. You can count on art-house films to be shown during Sunday Movie Club.
FESTIVALS AND FAIRS
Madison County hosts a festival or fair almost every month of the year, and the Covered Bridge Festival in October draws a crowd. View their event calendar to plan your visit.
TOUR CONSIDERATIONS
If you prefer a guided, two-hour tour of the covered bridges, the Madison County Chamber and Welcoming Center can arrange for one of their expert tour guides to ride in your vehicle and provide information on the history of the bridges, including the movie production, for a small fee.
FINAL THOUGHTS
My Iowan friends told me I’d love my trip to the state, particularly Madison County, and they were right.
I long for the day I can relax on the front porch at Covered Bridge House again or enjoy a delicious meal with a beautiful view of the Winterset courthouse.
I’m incredibly grateful to Madison County, Iowa Chamber & Welcome Center for hosting my visit. If you’d like more information about things to do in the area or upcoming events, follow their Facebook page.
It’s time you plan a vacation to Madison County, Iowa.
If you’re seeking another town to enjoy during your road trip, I recommend adding A Weekend in Fort Dodge, Iowa: A Delightful Getaway to your travel plans. It’s only two hours north of Winterset.
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