Dubuque To Waterloo: Events & Things To Do Along Highway 20 in Iowa (East) | USA

Last Updated on August 6, 2022

Highway 20 is America’s longest highway. Stretching from Boston, Massachusetts on the East Coast, all the way to Newport, Oregon on the West Coast!  It’s 3365 miles (914 miles longer than Route 66) crossing 12 States: Massachusetts, New York, Pennsylvania, Ohio, Indiana, Illinois, Iowa, Nebraska, Wyoming, Montana, Idaho and Oregon.  For the most part, Highway 20 sticks to its original 1926 Route across America.  When I moved to America, my house actually sat on the ‘Old Highway 20’ in Iowa! Ironically it’s somewhere that I’ve never really written about…until now! I spent almost everyday in the small towns along Highway 20 in East Iowa!

Disclosure: I have worked alongside some of the businesses listed in this post, however opinions are always my own!

Dubuque to Waterloo – Highway 20 Iowa

This road trip guide will take a look at Highway 20 Iowa between Dubuque and Waterloo. A stretch of around 90 miles!  I’ll share with you some of the cool things to see on Highway 20 and various events that happen along the Route!


Dubuque is the town ‘where Iowa started’. It is the first Highway 20 town in Iowa that you’ll get to when you cross over the Mississippi River from Illinois!  The Downtown Dubuque area has done nothing but improve.  Just in the time that I’ve been living in the USA (since August 2016), I’ve seen so many changes.  The biggest being the Millwork District which has lots of awesome cafes, restaurants and bars all within renovated old factory buildings.

Dubuque Millwork District Iowa

Other Dubuque attractions include:

  • The National Mississippi River Museum and Aquarium
  • The Fenelon Place Elevator
  • ‘Voice’ street art project (all over town)
  • Sky Tours Zip Lining
Millwork District Dubuque Mural

I have a whole guide for ‘Things To Do In Dubuque Iowa‘ that you may find useful.

There are loads of different restaurants to choose from in the area.  The more unique finds are in the Downtown area. But you’ll find all the usual popular chains in the business district area on the outskirts.  Some of my favourites are: ‘7 Hills Brewery‘ in the Millwork District and ‘The Barrel House‘ on Main St.

Fenelon Place Elevator Dubuque Iowa

Where To Stay in Dubuque

Again, like the restaurants, you’ll find a lot of the major chain hotels in Dubuque.  However I recommend the Hotel Julien on Main St or the Grand Harbor Resort overlooking the Mississippi River!

Hotel Julien Dubuque Lobby Area

Dubuque Fairgrounds

As you leave Dubuque, Highway 20 has two options.  You can either travel along the ‘Old Highway Rd’ which is the original route, or along the 4 lane highway which is faster but bypasses all the towns.

The Old Highway goes past the Dubuque County Fairground which holds many different events throughout the year.  Torque Fest (annually, first weekend in May) is a vintage car show with different types of car racing, music, show and shine etc.

Dubuque Iowa Torque Fest

The Dubuque County Fair is held during the last week of July.  There’ll usually be a couple of big music acts on the Friday and Saturday night, with smaller music events and entertainment throughout the week.  Of course being the Midwest, there are different farm animals on display, as well as fairground rides, side show games and all your favourite fair foods (deep fried ice cream cone I’m looking at you!).

Dubuque County Fair


A lot of the small towns on Highway 20 in East Iowa are typical community towns. Although President Trump did visit Peosta in 2018. They closed the exits on the new Highway 20 into Peosta during his visit!

The Red Roof Diner does good all day breakfasts. There’s one hotel, a grocery store, a Dairy Queen, a couple of gas stations etc.

Highway 20 Iowa Peosta Satan's Tunnel

I recently discovered Satan’s Tunnel which can be reached by going down either Cox Springs Rd (on the old Highway 20) or Thunderhills Rd (from the new Highway 20).  It used to be a single lane vehicle tunnel as a way of getting under the railway line.  The road through the bridge has subsided and is partly covered by a stream. It is now closed to through traffic.  However you can park at either side and still walk into the tunnel.  It’s covered in graffiti and is a fun place to photograph!

Highway 20 Iowa Peosta Satan's Tunnel

There are a couple of annual events worth mentioning…especially if you like 5k runs!  Outrun The Rays is a melanoma and sun safety awareness event with a 5k fun run and a bike ride. This takes place on the last weekend in May.  They give away free suncream to competitors and there’s a campaign to encourage high school students going to Prom to not use indoor tanning beds.

Peosta Days is an ‘end of summer’ event held during the last weekend in August.  Usually on the Thursday night before, there’ll be a 5k glow run and then on the Saturday there’s a parade, competitions and then fireworks in the evening to finish it off!


Highway 20 Iowa Epworth

Epworth is home to the Dubuque County ‘Freedom Rock‘.  This is an art project with the aim of there being a large painted rock in each county in Iowa.  For those that like geocaching, there’s one in this location!

Dubuque County Freedom Rock

The second Epworth landmark is the ‘Rock Island Caboose‘ in Tower Park (there’s another geocache hidden here and I’ve failed at finding it multiple times, so if you have any luck…PLEASE TELL ME WHERE IT IS!!!).  I’m not sure exactly what brought it to Epworth, as Rock Island is in the Quad Cities around an hour and a half away.  The caboose has a small museum inside it which can be opened with prior arrangement.

Highway 20 Iowa Epworth Rock Island Caboose

A fun event in Epworth is the ‘Town and Country Days‘ which is held annually on the first Saturday in August.  The high school has a 2 mile fun run to raise money for one of the clubs (I came 3rd in my age category one year and won an awesome Epworth medal!). This is followed by a parade, which usually has some sort of a theme.

Highway 20 Epworth

In the afternoon/evening, old Highway 20 is CLOSED to traffic as there is a street party with a rib cook-off, music and entertainment and games and a slip n slide in Tower Park. 2018 was the first year that they partnered with local Dubuque breweries and had FREE beer tasting until the kegs ran out. Once the freebies had gone (which surprisingly lasted quite a while), you could then buy full sized versions of the samples.

Highway 20 Iowa Epworth Town and Country Days


When driving between Epworth and Farley, keep an eye out on the left-hand side of the road…there’s a buffalo farm!  There’s not really anywhere to stop but you can see the buffalos in the field as you drive by!

Farley City Park is a nice open space with good play equipment and baseball diamonds.  It’s also the location of another Western Dubuque High School fundraiser…the annual Wingfest (last Saturday in September).  I would suggest arriving early, it starts at 11am, as the chicken wings sell out pretty fast!  The idea being is to sample as many as you want and then you vote for your favourite!

Highway 20 Iowa Farley Water Tower

Farley has a small bowling alley called Cobra Lanes which is open for ‘public bowling’ being 1pm – 6pm at the weekends.  It holds a lot of tournaments and bowling leagues so isn’t always available to the ‘general public’.  It’s a good little bowling alley and fairly cheap.  2 games of bowling and shoe rental cost me $6.

Highway 20 Farley Iowa

I recently took part in a scavenger hunt with work around Farley and Epworth and it was ridiculously fun!  We had to take photos with various objects and landmarks around town and collect things from local businesses!


One of the major attractions in Dyersville is the Field of Dreams movie site!  During the summer season they’ll hold ‘Ghost Sunday‘ events with ghost baseball players!  The site is completely free to visit both on event days and during regular opening times.

Field of Dreams Ghost Players

A big event that attracts people from all over the country, is the National Farm Toy Show, which is held twice a year on the 2nd weekend in June and the first weekend in November.  The National Farm Toy Museum is open everyday even when the show isn’t on.

The Plaza Antique Mall is worth having a nose in.  It’s in an old theatre building and even has full sized vintage cars inside!  It’s open daily between 10am – 5pm.

Dubuque Country Dyersville Antique Toys

In the main Downtown area of Dyersville, you’ll find the Basilica of St. Francis Xavier…it’s huge!  I also like the Dyersville Yoga Studio which has drop in rates.

Highway 20 Dyersville Basilica

Another big event in Dyersville is the St Patrick’s Day Parade and Bash with food, beer and live music.  In the morning there is the annual Gaelic Gallop fun runs (8k and 2 mile routes).  Now I love my fun runs but it always seems to be SO COLD in March!!

Highway 20 Iowa Dyersville St Patricks Day Parade

If you don’t want to drive Highway 20 between Dubuque and Dyersville, you’ll find the 26 mile ‘Heritage Trail‘ which runs along an old train line.  This is a crushed limestone hiking and biking trail.  Use of the trail does require either a day pass ($2) or an annual pass ($10) which can be purchased from various places in Dubuque, Epworth, Farley, Dyersville or from self registration tubes in the trail parking lots.

Related Reading: Things To Do in Dyersville Iowa near The Field of Dreams Movie Site


Earlville Midwest Pride In Your Ride

A fun event in Earlville is Midwest Pride In Your Ride Truck & Tractor Show.  This is held at the Tri-State Raceway on the first weekend in May (same weekend as Vintage Torque Fest in Dubuque).  All proceeds from the event are donated to the American Cancer Society’s Relay For Life.  There are parades that celebrate drivers that are cancer survivors and if a survivor wears a purple shirt on the event day, they receive free entry!  I enjoyed watching the truck drag racing and looking at the truck units!

Highway 20 Earlville Midwest Pride In Your Ride


Manchester has one of Iowa’s whitewater parks (a second being in Charles City)!  It’s completely free to use with your own equipment or you can rent tubes and kayaks from nearby businesses between Memorial Day and Labor Day.  It is a great free things to do along the Maquoketa River! Take a tube, a life vest and float along this short section of the river.

Related Reading: River Tubing at Manchester Water Park in Iowa USA | Everything You Need To Know

Highway 20 Delaware County Fair Manchester

If you haven’t had your fix of county fairs along Highway 20 Iowa yet, Manchester holds the Delaware County Fair during the 2nd week of July.  In 2018 they had a Hot Air Balloon glow where you could also have a tethered ballon ride!


Waterloo is the next biggest city along Highway 20 Iowa that you’ll reach after leaving Dubuque.  It is packed full of things to do, from the Lost Island Waterpark to the John Deere Tractor and Engine Museum.

Lost Island Water Park Waterloo Iowa

If you like nature you’ll enjoy the George Wyth State Park or maybe you could hire a bike and check out over 100 miles of cycling trails in the Cedar Valley!  You can see my full list of Waterloo recommendations in the following post: Fun Things To Do In The Cedar Falls/Waterloo Area!

Cedar Valley Nature Trail Cycling Trails in Waterloo Iowa

Where To Stay In Waterloo

Just like Dubuque, there are plenty of accommodation options in Waterloo.  If you are looking for somewhere that’s unique to Waterloo, you can stay in a converted John Deere factory building!  It’s now part of the Courtyard by Marriott chain but they worked hard to use features of the old building in their new renovations!

Courtyard by Marriott Waterloo Cedar Falls

Historic US Route 20

Highway 20 Iowa is currently going through the process of being Historic US Route 20.  Some of the tours along the route will be getting shiny new Historic Route signs and it’s getting a whole media campaign.  My friend Jay Jay over at The Iowa Gallivant has had a helping hand in bringing to life ‘Time To Be 20 Again’ and The 20 Tour!

Just like the Epworth and Farley scavenger hunt I took part in, The 20 Tour is a scavenger hunt that takes in all the Highway 20 towns in Iowa as well as those just across the border in both Illinois and Nebraska!  The idea being that you take a selfie or a group photo at the landmark listed in the scavenger hunt and then upload it to Instagram with the hashtag #the20tour and tag @historicroute20.

Driving in Iowa USA

The idea of the scavenger hunt is to pull you even further into the towns that are along the route.  Some of the landmarks are right on 20 but others you’ll have to search a little harder for!  Even as locals you can discover places in nearby towns that maybe you didn’t even know existed!

Highway 20 Iowa Events Calendar

March – St Patrick’s Day Parade (Dyersville)

May – Torque Fest (Dubuque), Midwest Pride In Your Ride (Earlville), Outrun The Rays (Peosta)

Ghost Sundays (Dyersville) & Whitewater Centre (Manchester) rental companies open for the season

June – Summer National Farm Toy Show (Dyersville)

July – Delaware County Fair (Manchester), Dubuque County Fair (Dubuque)

August – Town & Country Days (Epworth), Irish Fest (Waterloo), Peosta Days (Peosta)

September – WingFest (Farley)

November – National Farm Toy Show (Dyersville)

For must see stops along Highway 20 in Illinois, check out this post: Chicago To Galena Road Trip: Must See Stops in Illinois USA

For events listed in this post, please check events on outlets like Facebook for the correct dates.  Most can be found by just searching for the event name!

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6 thoughts on “Dubuque To Waterloo: Events & Things To Do Along Highway 20 in Iowa (East) | USA

  1. You totally skipped Independence between Manchester and Waterloo! We have the Wapsipinicon Mill, Wapsipinicon River, trails throughout town, Train Depot, and only the best 4th of July festivities in the entire state! I encourage you to research Independence!

    1. I never went there and I tend to only write about places that I’ve been! I lived in Epworth so I knew the rest of the route fairly well 🙈

      1. Well you better make some plans! 🙂 Maybe not this summer, but next!

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