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RAGBRAI Route Inspection Pre-Ride Day 2 – Atlantic to Winterset

  • 3 June, 2019
  • Andrea Parrott

We had a Sunday Funday in Atlantic, but now it’s Monday so… on to Winterset!

Today’s route clocks in at a solid 68.1 miles, with approximately 2,044 feet of climb. We had another good variety of pass through towns today, including Wiota, Anita, Adair, Casey, Menlo, Stuart (Meeting Town), Dexter, Earlham, and Winterset! Click this text for a map of the second day of RAGBRAI XLVII.

Today on the Route Inspection and on Monday of RAGBRAI XLVII we will celebrate 100 Years of the American Legion and their outstanding contributions through service to the community, state, and nation. Monday’s route from Atlantic to Winterset stops through seven communities with active American Legion Posts.

A perspective on the route from Scott G –

I probably have fewer training miles than most others in our group, so the flat terrain during the first part of the day was a welcome change from the hills of opening day.  We were chased by a storm for most of the morning, so the tail wind produced by that was also welcome.  We traveled along rail lines again for some of today which means level roads.  The roads were some of the best we’ve seen.  No real concerns from our crew.  Our rider count was down considerably from the previous day, with this being a work day for most of you.

It’s kind of a long haul to the meeting town in Stuart, but will be worth the wait.  The hills do kick in the second half of the day, but count on rolling hills instead of any real groaners.   Plan for lots of stops.  With the exception of the last stretch into Winterset, towns are all less than 10 miles apart.  That breaks up the day nicely.  If you don’t find what you want in one town, you can motor on down the road to the next one.  Of course we stopped in every town to sample the hospitality, something I strongly encourage.  Enjoy!


Wiota will be the first town as we leave Atlantic on Monday’s ride.  Wiota is populated by just 116 residents and is located just 6 miles outside of town.  At present time they might be selling a few items at the church but are really expecting riders to ride through to nearby Anita for breakfast.

The Wiota Steakhouse & Lounge has recently been recently remodeled and is near the church.  Wiota also hosts the annual Sweetheart Supper every February at the fire hall.


We had a hearty breakfast in Anita! They are fantastic hosts and are ready to serve a few more riders on RAGBRAI.

Historical or interesting things about your town:
Where in Iowa can you find “A Whale of a Town”? It’s Anita, of course! Located just 3 miles south of I80 and exactly ½ way between Omaha and Des Moines, riders will find a small town with plenty to offer. Presently, Anita is home to just under 1,000 people. One of the biggest questions locals get asked is if there is a Whale that lives in Anita’s 171 acre lake. Of course there’s not, but there are plenty of stories of local happenings that would make anyone realize it is truly amazing.

In 1869 a group of railroad officials named the station “Anita” after one of the officials niece: Anita Cowles.

Famous Citizens:
Krista Young: Creator of the “Hawkeye Wave”.

Bud Leff: Former director of Iowa High School Athletic Association

Earl Caddock: “The Bera Tiger” World Wrestling Title Holder 1912-1923

Troublesome Creek Gang

Infamous Events/Strange Happenings:
The Omaha World Herald and The Des Moines Register had a softball tournament played here in which the respecting governors were pitchers.

Interesting Buildings/Restaurants/Sites:
“The Old Town Clock” on Main Street is 103 years old. The Redwood Steak House is one of the longest running steak houses in Iowa. The Weathervane building sets true North/South. A Masonic Temple exists in city limits. Just north of Anita there is a famous “Tree in the Middle of the Road.” 80-year old generators are still available in case of a power outage.

Interesting Landscapes/Lakes/Parks, etc.
Anita is home to Lake Anita State Park, a 771-acre park with a 171 acre lake; Crestwood Hills Golf Course, an 18 hole public golf course; JR Karns Grass Roots Trail; Bandshell Park; Victory Park; 18-hole Disc Golf; Keystone park; and the Anita Health and Wellness Center.

2019 RAGBRAI pre-ride: Day 2, Atlantic to Winterset

2019 RAGBRAI pre-ride: Day 2, Atlantic to Winterset

Anything else you would like the participants of RAGBRAI to know about your town?Annual Events:

Largest Easter Egg Hunt is Southwest Iowa!

Christmas Walk—1st weekend in December

Steak Fry—1st weekend in August

Give a brief description of what the town is planning for RAGBRAI XLVII:
Anita is hoping to give riders a whale of a time during their stop. They are one of the first stops in the morning and will be providing many breakfast options for the riders. Follow Anita RAGBRAI on Facebook to stay up to date on what they will have to offer.

Type of food you plan to serve or vendors that will be in town (let us know if no outside vendors will be welcome to your town): Lots of breakfast options! Pancakes, burritos, french toast, frozen yogurt, fruit, sandwiches, smoothies, biscuits and gravy, pizza, baked goods, gourmet coffee, and cold drinks. Anita has many local vendors and will be allowing outside vendors as well.

Type of entertainment planned (bands, dance teams, contests, etc):
Toilet bowl races and numerous games/activities will be offered. Dave Gallagher will be providing DJ services.

Neat places that riders should be sure to visit (museums, attractions, etc.):
Lake Anita State park, golf course, numerous shops located on Main Street and their museum.

Neat restaurants or pubs that riders should be sure to visit:
Weathervane for breakfast, redwood steakhouse for supper, and sweet spot for lunch and supper. Be sure to visit the three bars on Main Street, Huffys, Shooters, and BJ’s Bar.

Any interesting stories riders should know about that is happening in town (recovering from natural disaster, fundraising effort for playground, etc.):
Anita is hoping to raise money to put towards their “project playground” fund. The band shell park is 30+ years old and sits in the heart of their downtown. It has been the center for many events hosted in their community. There will be whale tattoos and bracelets near the band shell park. All proceeds will go towards the new playground equipment.

Anita Town and Country will be teaming up with Chris Cakes to provide a pancake and sausage breakfast. Some of the proceeds they make will go towards the band shell park playground and other events they host throughout the year for the community.

Other events they host:
Angel tree program that provides kids in need with coats, shoes, and gifts for Christmas.

Christmas walk: Santa, free activities for kids, tour of trees.

They put on the largest Easter egg hunt in SW Iowa. This year they had over 500 kids that attended. Each kid gets a prize. Over 50 bicycles were given out and many other prizes.

Facilitate the town celebration “steak fry” which is held the first Saturday in August.

Donate supplies to the local schools and backpack program.

Host a Halloween party with a costume contest, trunk-or-treat, and dinner.

Donate to the food pantry numerous times throughout the year.

Does your town have a theme (and logo if you have one), let us know?
“Whale of a town”

For more info on Anita’s RAGBRAI plans visit:



During day two of RAGBRAI XLVII, the ride will follow the White Pole Road. The 26-mile byway connects the communities of Adair, Casey, Menlo, Stuart, and Dexter. This historic and scenic road was originally designated in 1910 as part of a river-to-river road. During the early 1900s, Iowa had a bad reputation in other states for terrible road conditions. The state got the nickname of ‘the gumbo state’ for near impassible roads during parts of the year due to snow and rain. On March 8-9, 1910, Governor B.F. Carroll called for a convention to plan a well-maintained state-wide road. The road went from Davenport to Council Bluffs. When building the road, Iowa (and the ten thousand farmers who construct it) set a record by assembling the 380-mile road—made mostly from existing dirt roads–in one hour.

The White Pole Road was built as part of a straighter, leveler, and shorter route from Des Moines to Council Bluffs. This route also had a town about every five miles. Towns had a big incentive to encourage visitors to stop. The more visitors who stopped in a town, the more businesses there would be, and the easier it was to stay on the map! To attract tourists, Adair, Casey, Menlo, Stuart, and Dexter painted poles along their portion of the route white and encouraged travel on the “Great White Way.”

In 1913, The Great White Way Association applied to be part of a proposed route from Chicago to Denver. It became the first certified route under the State Highway Commission’s rule—it was a named trail over 25 miles long. In 1931 a section of the White Pole Road officially became part of US 6, the longest continuous east-west route in the United States at the time. When Interstate 80 was completed in 1965, the popularity of US 6 dwindled. In 2003, the 26-mile of road was given to the surrounding counties and officially named the White Pole Road. The over 700 poles along the White Pole Road remain painted white and the communities continue to maintain the road.


You can’t help but smile as you pull into Adair.  The water tower has been a landmark along I-80 for years.  Their theme is “Smiles for Miles”.  The locals have a great day planned for riders as they come into town.  Fund raising for the new fire station and a new community center will be in full swing during the day RAGBRAI comes to town.  Adair will be

You’ll take a stroll through the park as you first come to town.  Once you leave the park you will head downtown where you will find food vendors and the beverage garden.  Be sure to check out the local restaurants Zipps and the Chuckwagon for bloody marys and the best burger in Iowa.  Also continue on down the street to visit the Fire Station at the end of vendor row.  You’ll also find the Catholic Church serving homemade ice cream.

Activities in town include:

  • Giant Beer Pong
  • Corn Hole/Bags
  • KSOM Live broadcast during the afternoon

Also worth noting, Jesse James robbed a train just outside of town.  Look for the historic site on your way into town.

You’ll find plenty to eat and drink in Adair, and you’ll leave with a smile!

For more info on Adair’s RAGBRAI plans visit:



Casey is planning on having a variety of vendors to serve us during RAGBRAI – and will be opening a new restaurant in time for the ride. If you’re not hungry, enjoy their park with the “old school” merry go round or take a quick stop at the brand new City Hall. Be sure to stop on your way out of Casey to check out the Jesse James historic site – it’s where the “first rain robbery in the West” occurred. It’s well marked and on the right side of the road just after you head out of town.

Historical or interesting things about your town:
Casey Catholic Church was built in 1908. It showcases beautiful original stain-glass windows. Visitors can go on a self-guided tour of the historic home of Jack Perishing—the famous rooster sidekick to auctioneer Dr. Jones. Together they raised $40,00 for the Red Cross during WWI.

Famous Citizens:
Thomas Duncan—Author of several award-winning selections.

Infamous Events/Strange Happenings:
1905 Train Wreck—Slayton Rock south of town at 1174 Fontanelle Road. Home to 500,000 16 plus foot tall glacier/boulder/rock that was moved in 1999.

Interesting Buildings/Restaurants/Sites:
Memorial wall on the main street (McPherson Street). Abram Rutt Bank, Rutt camping and park. Brand new Community building and City Hall.

Interesting Landscapes/Lakes/Parks, etc.
Rail Road Park—aka Kite Park—is located along the tracks and White Pole Road. Kite Park was named for Jesse Kite, the only soldier killed in WWI who lived in Casey. The VFW chapter was named for Jesse and became Kite Post.

Gray Par is located across the street from the Visitor Center at the corner of McPherson and Grant Street.

Rutt Park is the largest of Casey’s three parks. It is located off of Russell Street, where campers visit often.

Anything else you would like the participants of RAGBRAI to know about your town?
Casey is family friendly. Ag Adventure for all groups with farm animals. Displays will be located in town for the event. This will give riders a chance to see what happens on a farm and how farmers care for their animals.

For more information on Casey’s RAGBRAI plans, visit:



Founded in 1869 and originally call ‘The Switch,’ it was changed to Menlo when the Railroad was built to Guthrie Center. Menlo will be celebrating their Sesquicentennial (150th) in 2019.

Menlo Pioneer family’s that still reside in Menlo are: Varley family, Miller, Wildman (Luckinbill), Dickson, Cline, and Grooms.

The American Legion Post in Menlo, since 1919, is named ‘Glover-Buttler Post 511”. This is in honor of Menlo residents first killed in WW1 (Harold Glover) and WW2 (Richard Buttler). The oldest living member of the post is Robert Dickson (93) and the oldest living member of the Menlo American Legion Auxiliary is (93).

An interesting fact in town, seven sets of twins all in the same class. It makes you wonder, is there something in the water? Other points of interest include:

  • Menlo Oil Company gas station founded in 1934 still stands today with the ‘Old Man’ waiving sign. A great photo op.
  • The C.A. Wildman Grain and Coal Feed and Seed Company began in the early 1900’s. An old building is still on main street.
  • The Menlo Café has been cooking home-style food since 1980.
  • Since 2010, Flint Hills Resources Biofuels and Ingredients. Each year, Flint Hills buys 288 million bushels of corn from local farmers to produce 850 million gallons of ethanol.

A DJ will be playing music along Main Street, and Shorts Bar will be open and features a large outdoor patio with bean bag toss.


STUART (Meeting Town)

When the riders get to Stuart, there will be a number of ways they can kick back, relax, and enjoy themselves. Whether they choose to cool off at the local pool or get hosed off by the fire department for a $1. Hang out under a tree and listen to the live music or brush up on some local history at the Saints Center and Train Depot. Stuart guarantees there will be something for every rider.

At the depot, riders and drivers can find out about Bonnie and Clyde’s last bank robbery, which took place in Stuart in April 1934, and about the history of the depot and trains which made Stuart the town it is today. They can head over to the Saints Center to learn about this truly magnificent building where they will be able to tour the building and learn about its rich history and stunning architecture. They can watch a video about the fire that destroyed a piece of history and the subsequent renovation that pulled a community together.

If more of a party atmosphere is what riders and drivers are looking for, they can head downtown where Stuart have a beer garden supported by its local bars. Numerous games will be available including bags, giant pong, giant checkers, and giant Jenga. If horseshoes are more their game of choice, they’re in luck! Stuart have a number of pits available at the city park for their enjoyment as well.

All this excitement will surely make the riders hungry, so be sure to stop by Stuart’s volunteer Fire Department where they’ll be selling food to help raise money for equipment. The Iowa Corn Growers will be handing out free ears of sweet corn. Or help celebrate American Legion Day by stopping by Stuart’s local Legion and Auxiliary and purchase a pulled pork sandwich at their build located across from the pool. Maybe swing by the Congregational Church downtown and enjoy some A/C and a spaghetti dinner. Not to mention the countless local and non-local vendors located either in the park or downtown. There will be close to 30 vendors in the park including the Lions Clubs and Country Kitchen.

In addition, these local restaurants will be open for business: Burger King, Country Kitchen (also set up in the park), Linden Street Sweets, Los Altos Mexican Restaurant, Ruby’s Pub, Traditions Bar & Grill, Subway and McDonalds

Before heading out of town, don’t forget to stop by Guthrie County Democratic Committee’s booth and “Cast your Kernel” for President and enjoy some photo opportunities. Or head over to one of their picture boards and take some souvenir pictures to remember your time here in Stuart!    


For more information on Stuart’s RAGBRAI plans, visit:



Dexter is about 50 miles into Monday’s route, so they will be thirsty and hungry!  Dexter will have plenty of food and drink options when riders come to town. There will be vendors, entertainment and much more!

Dexter will have lots of food vendors in the downtown including the American Legion serving loose meat sandwiches and the Presbyterian Church is having a fundraiser selling homemade cookies and drinks . Dexter is still accepting applications.

Wine on Wheels will have a beer garden in town along with RAGBRAI faves DJ Jam Time!  The Rusty Duck will also be open for business.

Some neat places that riders should be sure to visit include the Roundhouse, Drews Chocolates, Dexter Museum, Bonnie and Clyde Shootout at old Dexfield Park, Location of President Trumans campaign stop for National Plowing Match; and the Soil Conservation Field Day in 1948

For more information on Dexter’s RAGBRAI plans visit:



It was rainy and cold by the time we visited Earlham but they still came out and welcomed us. The weather will be much better in July, promise! They have some fantastic plans in store for us so that you’ll leave the last pass through town of the day relaxed, full of good food, and happy.

Historical or interesting things about your town:
John Wayne lived in Earlham longer than in Winterset. Earlham was founded in 1896. The Underground Railroad was very active in this community. The first Railroad to go through Madison County came through Earlham.

Famous Citizens:
John Wayne

Interesting Buildings/Restaurants/Sites:

  • Bricker-Price Block—see attached
  • Hare and Hound—Wood fired pizza
  • See website for full list of businesses

Interesting Landscapes/Lakes/Parks, etc.
City Park will host activities day of ride, including a stage w/ band.

Anything else you would like the participants of RAGBRAI to know about your town?
Earlham is very vibrant and has many businesses including lawyer office, dentist, doctor, chiropractor, hardware, vet, bank, grocery store, pharmacy, insurance, Retail shop called Rescued Junk, and many other businesses.

Plans for RAGBRAI
During RAGBRAI, Earlham will have a DJ in the beer garden, live music in the park, and wrestling.

Food will include smoothies, brisket, Cardinal Chops, pork tenderloin, fried taco, philly steaks and cheese sandwich – the last three all at the West Side Bar and Grill, which we visited and we can tell you, it’s tasty! And more to come…

Type of entertainment planned (bands, dance teams, contests, etc):
A DJ, live music in park, and wrestling

Neat places that riders should be sure to visit (museums, attractions, etc.):
The downtown and city park

Neat restaurants or pubs that riders should be sure to visit:
West Side Bar and Grill, the Hare and the Hound/Bricker Price Block

Any interesting stories riders should know about that is happening in town?
A non-profit in town received a grant from Levitt Amp Music for 10 free concerts in the city park this summer. Also, Thanks to a tourism grant from the Iowa Economic Development Authority, they have kicked off a branding campaign called #EarlhamExperience. Through social media and numerous print mediums (including a RAGBRAI themed selfie station), they are showcasing their local businesses and the amazing events coming to their great, rural community of Earlham, Iowa.

Town theme/logo:
#Earlham Experience

For more information on Earlham’s RAGBRAI plans visit:



Winterset was organized in 1849 and nearly named “Summerset.”  The tale states that during a bitter winter, the first county commissioners met to decide the town’s name.  Several names were mentioned and rejected.  While mulling over the name Summerset, a local citizen rousted from the bench where he was reclining and that “you had better call it WINTERset” in derision, due to the deep snow that consistently fell in that season.  After finding that the name Winterset would be unique among US post offices, the commissioners adopted it.  Their railroad spur arrived in 1872 which fueled business and housing development.  The original train depot can be seen at the Madison County Historical Complex.

Winterset is a vibrant and growing community with a population that is approaching 6,000, up from the 5,200 in 2010 plus unprecedented growth is anticipated in the next few years. With this growth will come new businesses, industry and residents.  The City, in conjunction with the downtown building owners around their Courthouse Square, will soon complete a façade rehabilitation project that will only enhance an already beautiful setting.



  1. Six Covered Bridges, one in the Winterset City Park
    Madison County has six covered bridges, the largest number in one area in the Western half of the Mississippi Valley. Originally there were at least 20 and they were built to protect the bridge boards from deterioration by weather on the more heavily traveled roads. The Cutler-Donohue Covered Bridge has been relocated in the Winterset City Park.  Charles hosts the Imes Bridge at the edge of the town. Cedar Bridge, just now completing a second re-creation after two arsons, is just northeast of Winterset and three other original bridges are spread around Madison County on rock roads, all awaiting exploration.
  2. Winterset Courthouse Historic District
    The nine-block area surrounding the Madison County Courthouse is the county’s only Historic District, designated in 2015. It contains 78 buildings that were thoroughly researched to determine their historical significance.  All the buildings were in place in 1899 and represent the development of Winterset throughout the years.  The district is anchored by the grand 1876 Madison County Courthouse.   com
  3. Madison County Historical Complex
    Located on the south side of Winterset, the Complex has 14 buildings on 18 acres and contains the 1856 Victorian Bevington Mansion, an 1881 church with an active congregation, agricultural barn, log and frame school houses, 1872 Winterset Train Depot, and more. The museum’s collection holds business and domestic displays, farm machinery, military items, and quilts to represent a lasting record of the life and livelihood of Madison County people.      com

Famous Citizens:

  1. George Washington Carver
    George W. Carver arrived in Winterset in the fall of 1888 after being turned away from college in Kansas. Although discouraged about his educational possibilities, he became an active member of the Winterset community: working in a hotel kitchen, taking in laundry in his home, roaming the hills studying nature, and participating in the First Baptist Church choir.  There he was noticed by Mrs. Helen Milholland who invited him into the Milholland home to enjoy their mutual interests of plants, art, and music.  Through the family, he was encouraged to enroll in Simpson College in Indianola in 1890 which set him on a course to Iowa State College, the Tuskegee Institute, and his scientific contributions to the world at large.  Winterset has a pocket park, located one-half block east from the Courthouse on Court Avenue on the site where he worked, dedicated in his memory.
  2. George Stout
    The story of this Winterset son was told in the 2014 George Clooney movie, “The Monuments Men.” Stout was born in Winterset and graduated from Winterset High School in 1916.  He later graduated from the University of Iowa, served in World War I, and become a known art conservator at Harvard’s Fogg Museum.  In World War II, he was recruited to the Army’s Monuments, Fine Arts, and Archives section (MFAA) where he supervised the inventory and removal of several thousand works of art from enemy repositories.  A sculpture to his memory and contributions is located one block south of the Courthouse on First Avenue, on the grounds of the high school where he first plied his artistic talents.
  3. John Wayne (Marion Morrison)
    Born in Winterset in 1907 to a local druggist and his stylish wife, the young Marion moved with his family to several places in Iowa and back to Earlham in Madison County before their move to California when he was nine years old. His career in the movie industry resulted in parts in 142 movies and he was a top box office draw for three decades.  Winterset is the home of the John Wayne Birthplace and Museum, the only museum in the world dedicated to John Wayne, and holds the largest diversified exhibit of John Wayne artifacts in existence.
  4. Uncle Henry Wallace

Believing in progressive agriculture, Wallace’s family includes two Secretaries of Ag and a VP candidate.

Infamous Events/Strange Happenings:

  1. First Winterset Stone Courthouse Burns
    The beautiful limestone courthouse at the center of Winterset is the second stone courthouse in that spot. With great pride and $75,000, Winterset built a limestone courthouse on that spot in 1868-1869.  Although local citizens called for the purchase of fire insurance, none was acquired.  On October 2, 1875, a fire of unknown cause burned out the wooden structure within the young courthouse and the bell fell, melting on the basement floor.  Undaunted, plans for a slightly larger replacement began immediately at the cost of $116,000.  The architect was Alfred Picquenard, who was also building the Iowa State Capitol at the time.  The courthouse has an all-brick interior within the limestone walls to make it fireproof and has continuously served as the center of justice and county offices since that time.
  2. Underground Railroad
    Madison County was located on a very active section of the Underground Railroad in southwestern Iowa. Local researchers have documented over 90 participants during the years 1857 through 1862. Prominent Winterset businessmen seemingly funded the work while farmers and their families put their lives in danger in the effort to assist the Freedom Seekers (fugitive slaves) on their way through rural Madison County and on to freedom.  Under the threat of large fines and lengthy imprisonments, the stories of the determination of those engaged in this cause is an inspiring example of courage.
  3. World War I Memorials
    In the Winterset Cemetery there are 51 engraved stones representing the 51 Madison County young men who died in WWI. At their center is a bronze WWI soldier atop a 14-foot shaft.   Satellite images and drone photos have helped citizens realize that the scattered stones form a five-pointed star.

Two of the young men represented by the stones have an eerie story.  Russell Salisbury and Joseph Downs of Patterson enlisted on June 30, 1917 and commemorated the event by erecting a flag pole in front of the Salisbury home.  Before the cement at the base dried, each one inscribed his name followed by the phrase “SHOT IN FRANCE.”  In the early morning of May 27, 1918, the enemy launched a gas attack across the trenches where Salisbury and Downs were serving in France.  Both were fatal victims, along with 500 other US troops.  In 1923, the flag pole base was dedicated as a monument to their service and can be seen in the town of Patterson.

  1. Delicious Apple Tree
    This widely known variety of apple was discovered southeast of Winterset by Jesse Hiatt. Hiatt was a family man with fruit-growing knowledge when he arrived in Madison County in the mid-1850s.  He was experienced with seed selection and grafting several varieties onto one tree.  In the spring of 1872, he noticed that a yellow Bellflower apple seedling, thought to have died, had sprung up a green shoot.  A few years later, it bore a unique fruit – with a red and yellow streaked skin and five rounded knobs at its base.  Hiatt named the new type of apple “Hawkeye,” using Iowa’s state nickname.  After entering his new apple in several fruit shows, the Stark Brothers Nursery obtained the sole rights to the apple in 1894 and used a name they have been hankering to use for some time, “Delicious.”  Or so the story goes.
  2. Oldest Oak Tree in Iowa
    Madison County is home to the oldest tree in Iowa which has been determined to be approximately 385 years old. That places its germination around 1634, not long after the Pilgrims arrived at Plymouth Rock in 1620.
  3. Jailbreak

The same tunnel was used three times!


Interesting Buildings/Restaurants/Sites:

  1. The Iowa Theater
    Built in 1899, this space is part of the Winterset Courthouse Historic District and has been a theater for just over 100 years. In 2017, it was rehabilitated into a modern theater with digital film.  This labor of love, by Marianne Fons and daughter, Rebecca, is a favorite place for locals to watch new movies, experience old ones on Way Back Wednesdays, and live stage presentations.
  2. Northside Café
    Part of the Winterset Courthouse Historic District, this 1875 building has consistently held a restaurant for 140 years. The Northside name has existed since the 1940’s.  Clint Eastwood sat at a stool there in the 1994 movie “The Bridges of Madison County” his coffee cup still in place to this day.                 Facebook: Northside Cafe
  3. First United Presbyterian Church
    This church at Green Street and 2nd Avenue was built in 1876 for $14,000. It was contracted by Eli Cox, a frequent builder of covered bridges, with brickwork by Thomas Mardis who laid the brick for many of the buildings in the Courthouse Historic District.  Its original stained-glass windows are still in place.  A tale is told that Eli Cox did a head-stand at the top of the 112-ft spire before putting the pointed top in place.
  4. Homes on Jefferson and Court
  5. Contractor refuses to hand over keys to First Stone Courthouse

Interesting Landscapes/Lakes/Parks, etc.

  1. Winterset City Park
    The Winterset City Park began with barely 15 acres in 1872 and served as grazing pasture for the town’s cows and a dumping place for the town’s trash. But in 1912, local groups took an interest in providing a true city park, as pristine as those they had seen on their travels throughout the United States.  Generous bequests in those early years increased the park system to 132 acres.  A Park Commission was formed, and a landscape architect was consulted over the next 15 years to improve the park by selecting plants and trees, adding scenic roadways, and providing picnic and play areas.

The Winterset City park holds several unique features including three limestone shelters, an 1894 pioneer cabin, a 1922 monument to the Delicious Apple, three limestone bridges, an English hedge maze, the historic Cutler-Donahoe Covered Bridge, and a lovely driving trail through the timbered portion that leads to Clark Tower.  Caleb and Ruth Clanton Clark were very early Madison County pioneers whose family has been stone masons for generations.  In 1926-1927, their children opened a small quarry in the park and built the two-story limestone tower to their memory that now provides wide views into the countryside over the Middle River valley.

  1. Pammel State Park
    Pammel Park, one of Iowa’s first state parks, was dedicated in 1928 and named for Dr. Louis Pammel, well-known Iowa State University Professor of Botany. The park covers 350 acres and is known for its natural woodland beauty highlighted by its signature limestone ridge known as the “backbone”.   Drive through its limestone tunnel which was first dug to divert water from the Middle River in the 1880’s to power the Harmon Mill on its east side.  Pammel is home to a lush diversity of woodland vegetation, wildflowers and native plants, and quality stands of Walnut trees and is a popular place for picnics, hiking, and camping.
  2. Covered Bridge Scenic Byway
    Madison County has been designated by travelIOWA as an Iowa Scenic Byway Route featuring the central, north central, northeast and southeast regions of Madison County. The Scenic Byway includes 82 total miles of highways and county roads featuring all the glorious scenery that is Iowa: rolling hills and valleys, beautiful farmlands, century farms and cultural and historic landmarks. Over 120 sites highlight scenic natural areas, historical sites, cultural sites, and many other unique destinations.     


  1. Annual Covered Bridge Festival
    On October 12-13, 2019, Winterset will host its 50th Annual Covered Bridge Festival. The first Madison County Covered Bridge Festival was held in 1970, started by a group of active and passionate citizens.  Some things have changed since its inception, but they still honor their six remaining bridges with regular tours throughout the weekend and a popular “Meet Me at the Bridge” celebration on the Saturday evening of the festival. There are craft booths around the Courthouse Square, many displaying hand-made goods made by local artists: pottery, quilts, doll clothes, paintings, drawings, photographs, jewelry, woodcrafts, fiber arts, and more.  An array of old-time activities are available, including an antique tractor ride, a Civil War fashion show, sheep-shearing, wool spinning, a corn box for the kids to play in, Passport to the Past activities at the Madison County Historical Complex (penny candy sales, horse and wagon rides, old-fashioned school lessons, a Civil War reenactment, etc.), and the annual Antique Vehicle and Covered Bridge Festival Parade. Visitors can also attend an old-fashioned spelling bee and other entertainment on the Courthouse steps, an antique car show, and a quilt show with many heritage quilts displayed.
  2. Bridges of Madison County – Movie and Book
    Madison County inspired Robert Waller’s 1992 book, “The Bridges of Madison County,” one of the greatest love stories of our time. The 1994 movie was filmed in Winterset, throughout the Madison County countryside, and at several of their historic Covered Bridges.
  3. Iowa Quilt Museum
    Opened in 2015 with the mission to promote appreciation of the American quilt and the art of quilting through displays of quilts and information about quilt history. The museum offers changing exhibits—three to four per year—of American quilts both vintage and new.  Marianne Fons, Winterset resident, lent her talents to the creation of the Iowa Quilt Museum.  Marianne, with her friend, Liz Porter, are well-known throughout the world for their quilting expertise, long-running Public Television shows, books, and as editors and owners of the magazine, Fons & Porter’s Love of Quilting.       org

The Iowa Quilt Museum houses the national headquarters for the Quilts of Valor Foundation is a group of volunteers throughout the United States who make and then award quilts to any service person, no matter when or where they served.  As of 2019, over 200,000 quilts have been presented.

Anything else you would like the participants of RAGBRAI to know about your town?

  1. Freedom Rock
    The Madison County Freedom Rock, located next to the John Wayne Museum, is Ray “Bubba “Sorensen’s 64th completed rock. Sorensen paints Freedom Rocks to thank their Veterans and to promote Iowa tourism.  Each one is unique and tied to the community where it resides.  This rock features four Madison County Prisoners of War, native sons George Stout and Glenn Martin (early aviator, inventor of the Martin Bomber, and principal of Lockheed-Martin), a woman veteran draped in a Quilt of Valor, and four images of John Wayne in various military movie roles.
  2. Monumental Park
    In the aftermath of the Civil War, local citizen built a monument in memory of those who served from Madison County. The base, of native limestone, was dedicated in October 1867 is one of the first Civil War monuments west of the Mississippi. By 1880, it was flanked with four Civil War era cannons.  It has the local name of “Cannonball Park” due to the stack of cannonballs beside each cannon. A time capsule was hidden in one corner of the base and rediscovered in 1974.  The park, just one block east of the Courthouse Square has been a cool respite for generations of residents, farmers in town for Saturday night shopping, and children playing in the grass.
  3. Wineries / Cidery
    Madison County boasts a cidery and three craft wineries that provide unique taste experiences and entertaining live music.
  4. Winterset Art Center
    Established in 1958, the Art Center promotes artists and active engagement with the arts through classes, events, exhibitions, and patronage of regional artists. It is a vital gathering space for the community that encourages artistic expression, engagement with the arts, and development of artistic ability.


Plans for RABGRAI:

To help RAGBRAI riders celebrate their 70-mile accomplishment, Winterset will treat everyone like a grand champion when they arrive on Monday, July 22. Themed, “Winterset: Where Everyone’s a Winner,” riders will bike into a race-like atmosphere, complete with a finish line, music, a time clock and medals. This theme was chosen to celebrate Winterset’s numerous accomplishments, as well as play-off of the growing popularity of the participation trophy. Also, you can’t spell Winterset without “WIN!”

There will be plenty of welcoming places for riders to camp, including the main campground at the Madison County Fairgrounds, and lush green space in the Winterset City Park. The Fairgrounds will offer food and entertainment for riders, and school bus shuttles to quickly and conveniently get riders downtown to the main attractions.  The Winterset City Park boasts of nearly 80 acres containing three limestone shelters, play equipment, RV camping area, hedge maze, pioneer log cabin, and one of the famous Covered Bridges of Madison County, the Cutler-Donahoe bridge. Riders can also cool off at the Winterset Aquatic Center, complete with slides, sprays, zero-depth entry, and plenty of shade and grass for relaxation. And for those riders who just haven’t had enough exercise for the day, there are tennis courts near the aquatic center.

Famous for Robert Waller’s book and subsequent 1994 hit movie, The Bridges of Madison County​, and the birthplace of John Wayne, Winterset has a plethora of historic sites for riders to take in. A special Winterset Landmarks bike loop is planned for those history buffs out there and will take riders past the Cutler-Donahoe Bridge built in 1870, Clark Tower, a limestone tower built in 1926 as a memorial to one of the county’s earliest pioneer families, and the 6,100 square foot John Wayne Birthplace Museum, which includes the largest diversified John Wayne artifacts exhibit in existence. In addition, riders have the opportunity to visit Winterset’s Freedom Rock, the George Stout sculpture (World War II soldier portrayed by George Clooney in the movie The Monuments Men​), The Iowa Quilt Museum, The Madison County Historical Complex (14 buildings on 18 acres), and their historic and newly restored movie theater, The Iowa.

For those ready to sing and dance the night away, Winterset will have two entertainment stages offering a variety of entertainment throughout the day. Their opening act, IV Play, will get the party started.  IV Play will be followed by an all-out, over-the-top, exciting performance by their headliner, Here Come the Mummies, an eight-piece funk-rock band of 5,000-year-old Egyptian mummies. This nationally-known group is made up of artists from other bands who keep their identity secret by dressing up in mummy garb.  Riders can quench the thirst they’ll work up enjoying this out-of-this-world entertainment by visiting one of their two beer tents, complete with a local, craft beer tent.

For those more interested in taking in the scenery, downtown Winterset will not disappoint. Take a stroll through the Winterset Courthouse Historic District, placed on the National Register of Historic Places in 2015, complete with an 1876 limestone courthouse, surrounded by buildings on the square that have been historically intact since 1899. The beautiful square is also home to many thriving local businesses, including restaurants, coffee shops and retailers.

No matter what type of entertainment riders are in the mood for, Winterset will be sure to please. Cool off at the public library, stop by the skate park, take in a movie at the theater, feast on a home-cooked meal (and pie!) served by one of their many churches, or just relax and take in the atmosphere in the courthouse green space. They’ll help riders get to wherever they want to go by offering shuttles throughout the day, as well as to and from the campgrounds.

For more information on Winterset’s RAGBRAI plans, visit:

We recorded a preview of our journey from Atlantic to Winterset on the JustGoBike Podcast! Listen here:

Be sure to check back every day this week for updates and photos from the route inspection ride here on the RAGBRAI  site You can also follow the pre-ride adventure and learn interesting tidbits about the route by following on Facebook or on TWITTER by following @RAGBRAI_IOWA@TJRAGBRAI, or @RAGBRAI_Andrea


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