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Date:
Sat, Jun 13, 2026 at 6:45 AM – 7:30 PM
Location:
4350 Mounds Park Road
Town of Blue Mounds, Wisconsin
53517
United States
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Links:
friendsofbluemound.org Register at runsignup.com
Tags:
Cycling

Three routes, two county tours, one result: a painfully fun, must-do biking experience destined to find its way onto your June calendar for years to come.

2026 marks the 23rd Horribly Hilly Hundreds. Commonly referred to as the "Suffer fest of the Year" and "The Toughest One-Day Challenge Ride in the Midwest" is not to be missed by serious riders anywhere.

Since 2003, Horribly Hilly participants have enjoyed a day of riding that results in an awe-inspiring accumulation of 10,000 feet of elevation gain in the Driftless Area of Wisconsin. Growing in popularity each year, although not a lotter anymore the Horribly Hilly registration has reached capacity each year months prior to the event. A second and third route option beyond the original course were added in 2005 and 2011. How hard do you want to push it? Choose between the 100K, 150K, and 200K routes. The day is capped with a meal featuring quality local food and beer.

Approximately 1,200 riders test their mettle on southwestern Wisconsin's scenic byways each year in the Horribly Hilly. Join the ranks of an inspired community of riders for the premier cycling event in the Badger State and beyond.

For full details of this event, please visit our website: HERE

More cycling events nearby

  • Tri 4 Schools Waunakee Kids Triathlon [activeyouthwisconsin.org] [Register at runsignup.com]

    Sat, May 16, 2026 at 8:30 AM

    Description

    Tri 4 Schools is a part of Active Youth Wisconsin, a nonprofit committed to empowering kids to be happy, healthy, and confident through movement. To support this mission, we donate 100% of youth...

    Tri 4 Schools is a part of Active Youth Wisconsin, a nonprofit committed to empowering kids to be happy, healthy, and confident through movement. To support this mission, we donate 100% of youth entry fees to the participants' schools.

    We offer 4 in-person course options for this race. While there are recommended ages listed below, please select the course that best matches your child’s ability, regardless of age. Athletes must be able to navigate the course themselves and follow signage and volunteer directions along the course. Only athletes are allowed on the course; spectators/parents may spectate from the side. Note that the Long Course is only open to athletes age 7 and older. If your athlete uses a bike with training wheels, they must be registered for the Short Course. There is also an At-Home Course for participants who are interested in a virtual option. We strive to make our events accessible for children of all abilities; please contact us if you would like to discuss any specific accommodations for your athlete.

    Long Course (recommended ages 11-14): Swim 100 yards (4 lengths of the pool), Bike 4.3 miles, Run 1.1 miles

    Medium Course (recommended ages 7-10): Swim 50 yards (2 lengths of the pool), Bike 2.1 miles, Run 0.6 mile

    Intermediate Course (recommended ages 7-10): Swim 25 yards (1 width of the pool), Bike 2.1 miles, Run 0.6 mile

    Short Course (recommended ages 3-6): Swim 25 yards (1 width of the pool), Bike 0.45 mile, Run 0.08 mile

    At-Home: Complete your race wherever and whenever you like! Please follow all traffic rules and safety recommendations as you complete your race.

    35.2 km from Town of Blue Mounds
    301 Community Dr., Waunakee, Wisconsin, 53597, United States
    OpenStreetMap Google Maps

    Kids Run Swim Triathlon Virtual

  • Tunnel to Towers 5K Run & Walk - Madison, WI [runsignup.com]

    Sat, May 30, 2026 at 9:00 AM

    Description

    What is a Tunnel to Towers 5K?

    The Madison-area Tunnel to Towers 5K Run & Walk is a non-competitive event honoring the heroic life and legacy of Stephen Siller, a New York City firefighter who lost...

    What is a Tunnel to Towers 5K?

    The Madison-area Tunnel to Towers 5K Run & Walk is a non-competitive event honoring the heroic life and legacy of Stephen Siller, a New York City firefighter who lost his life on September 11, 2001. After learning of the attacks at the World Trade Center, Stephen strapped on his gear and ran through the Brooklyn Battery Tunnel to the Twin Towers, where he made the ultimate sacrifice.

    The event is part of the National Run, Walk and Climb series sponsored by the Tunnel to Towers Foundation. The event includes an opening ceremony honoring 9/11 victims and celebrating local first responders and military members who continue to serve with courage and dedication. Following the opening ceremony, participants run or walk 5 kilometers (3.1 miles) to commemorate the fallen. More information about the Foundation can be found at t2t.org.

    Where is the event? Why does it say Madison if it’s in DeForest?

    The 5K will be held at Veterans Memorial Park, located at 209 N. Main Street, DeForest, WI 53532. While branded as a Madison event, the park is approximately 10 minutes from Madison’s northeast side and about 25 minutes from downtown Madison, making it easily accessible to the greater Madison area.

    A drinking fountain and portable toilets will be available within Veterans Memorial Park. The park also features monuments to our nation’s military that you are welcome to visit.

    What is the course like?

    The 2026 course follows an updated route through the Village of DeForest trail system. The revised layout incorporates a loop to reduce congestion and minimize backtracking, offering participants a smoother and more enjoyable experience.

    • The entire route is paved

    • Most sections include a gravel or grass shoulder for participants who prefer those surfaces

    • Curb cuts are provided for accessibility

    • The course is primarily flat, with approximately 50 feet of total elevation gain/loss

    • Two water stations will be present along the route with water and healthy snacks at the finish area

    Will the event be professionally timed?

    For 2026, a professional timing company will be used. Although the event remains non-competitive and focused on remembrance and service, participants will receive official timing results for personal reference. Please note that the course closes 2 hours after the 5K begins to account for attendee safety and to allow for clean-up in a timely manner.

    Do I have to wear my bib number?

    Participants must wear their bib number clearly displayed on the front of their outermost garment in the chest or abdominal area. Individuals without a visible bib will be asked to leave the course and will not be allowed to finish. The bib is also what is used to time participants, so it must be worn for this reason as well. Be sure to wear the unique bib assigned to you to ensure your time is correctly recorded.

    Will there be awards for running?

    Our 2026 event does not plan to offer awards. The focus remains on honoring the fallen and supporting first responders and military service members rather than competition.

    What can I bring with me for the run/walk?

    The course is fully accessible and accommodates:

    • Strollers

    • Wheelchairs

    • Firefighter turnout gear

    • Military backpacks, ruck sacks, and weighted vests

    Participants are encouraged to leave personal belongings and valuables secured in their vehicles. The Tunnel to Towers Foundation is not responsible for lost or stolen items.

    Can I bring my dog or service animal?

    Dogs are permitted in accordance with Village of DeForest regulations and must remain leashed at all times. Owners are responsible for cleaning up after their pets. Trained service animals are always welcome and must also comply with Village regulations.

    Is there parking available?

    Approximately 30 parking spaces are available at Veterans Memorial Park. Additional street parking is available within a half-mile of the park, including Acker Parkway and Holum Street. All event attendees are reminded to observe all posted parking regulations.

    What registration details should I know?

    Online registration will remain open until 9:00 a.m. on event day. On-site registration assistance will be available from 7:30 a.m. to 8:30 a.m.

    • Please consider registering early as registration fees increase periodically after the event is announced with the final price increase occurring on event day

    • Event shirts are not guaranteed for participants registering after May 10

    Once registered, no refunds will be provided for any reason including if a participant cannot make the date or if the foundation must cancel the event due to extenuating circumstances. Registrations may be transferred to another participant until Wednesday, May 27 by contacting MadisonRun@t2t.org. When transferring a registration to another participant, shirt sizes cannot be changed.

    What should I know about fundraising? Is it required?

    Fundraising is not required to participate. Participants are encouraged to fundraise in support of the Tunnel to Towers Foundation. Upon registering online, participants will be able to set up an individual fundraising page if desired. As a gesture of gratitude, the Foundation offers amazing incentives. Participants are encouraged to explore employer matching gifts to maximize their contributions. Check out the Fundraising Guide for the latest information. Please note, registration fees do not count toward fundraising totals.

    What are my options for packet pick up?

    Early packet pickup will be available on Friday, May 29, from 4:00 p.m. to 6:30 p.m. at Fleet Feet Sun Prairie (2816 Prairie Lakes Drive #101, Sun Prairie, WI 53590).

    Event-day packet pickup will be available on Saturday, May 30, from 7:30 a.m. to 9:00 a.m. at Veterans Memorial Park (209 N. Main Street, DeForest, WI 53532).

    Packets may be picked up by another individual with a copy of the participant’s registration receipt.

    I’m visiting from out-of-town. Do you have any hotel recommendations?

    There are numerous hotels in the area. Spark by Hilton Madison Central is a proud sponsor of our event and is offering a special rate of $79 per night for event travelers. The hotel is located at 102 E. Rusk Avenue, Madison, WI 53713, about a 25-minute drive from the start/finish line.

    To receive the special rate, book by Friday, May 8, using the link T2T at Spark by Hilton Madison Central, or call 608-284-1234 and ask for the Tunnel to Towers 5K block. For questions, please contact the hotel directly. Thank you for supporting our sponsors!

    How can I learn about my business becoming a financial sponsor or donating goods or services to the event?

    Organizations interested in sponsoring the event through a financial contribution or by donating goods or services should contact MadisonRun@t2t.org for more information. Various sponsorship levels are available with included perks. The event team aims to respond to email inquiries within 48 hours or two business days.

    How can I volunteer for the event?

    Volunteers are needed for event-day operations. Individuals may sign up through the event website or by emailing MadisonRun@t2t.org. Verification letters for service hours are available upon request following the event.

    What measures are being taken to promote health and safety?

    The event will comply with all applicable local and state health guidelines in effect at the time of the event. An emergency medical service team will be present on site, with radio communication available throughout the course for emergency medical needs.

    47 km from Town of Blue Mounds
    209 N. Main Street, DeForest, Wisconsin, 53532, United States
    OpenStreetMap Google Maps

    5k Gravel Run Trail Walk Wheelchair

  • Fitchburg's Brewery Ride [runsignup.com]

    Sat, Jun 06, 2026 at 10:00 AM

    Description

    Take a bike tour of Fitchburg's local breweries, including the Great Dane Pub & Brewing Company, Delta Beer Lab, and Hop Haus Brewing Company. This ride will give riders an opportunity to explore...

    Take a bike tour of Fitchburg's local breweries, including the Great Dane Pub & Brewing Company, Delta Beer Lab, and Hop Haus Brewing Company. This ride will give riders an opportunity to explore local bike trails along the way and discover what makes Fitchburg a top biking destination! Each stop will have snacks and beer samples to try (for those 21+), and swag giveaways. Every brewery has non-alcoholic beverages available, too!

    All proceeds from the 2026 Brewery Ride will go to Fitchburg's Cycling Without Age Chapter, a local non-profit on a mission to offer people who cannot ride a bike themselves an opportunity to feel the wind in their hair as they ride as a passenger on a trishaw with a certified, trained pilot.

    29.7 km from Town of Blue Mounds
    Verona Road, Fitchburg, Wisconsin, 53719, United States
    OpenStreetMap Google Maps

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  • Wisconsin Triathlon Series [runsignup.com]

    Sun, Jun 07, 2026 at 7:00 AM

    Description

    WTS

    38.7 km from Town of Blue Mounds
    2829 Royal Ave, Madison, Wisconsin, 53713, United States
    OpenStreetMap Google Maps

    Triathlon

  • Loop the Lake - A bike ride to benefit our lakes [cleanlakesalliance.org] [Register at runsignup.com]

    Sat, Jun 20, 2026 at 9:00 AM

    Description

    Support clean, healthy lakes with Clean Lakes Alliance’s 14th Annual Loop the Lake Bike Ride. Join us in person on the official Monona Lake Loop by starting and ending at Olbrich Park on Saturday,...

    Support clean, healthy lakes with Clean Lakes Alliance’s 14th Annual Loop the Lake Bike Ride. Join us in person on the official Monona Lake Loop by starting and ending at Olbrich Park on Saturday, June 20th, 2026.

    Loop the Lake is more than a bike ride – it’s an opportunity for our community to rally around our lakes! All registered participants* will receive a super-soft event t-shirt, while supplies last (Shirt sizes range from youth small to adult 4XL). Event proceeds will support Clean Lakes Alliance’s work to protect and improve our lakes through on-the-ground projects, educational programs, and water quality monitoring.

    REGISTER SIX (6) RIDERS AND RECEIVE 25% OFF! DISCOUNT WILL BE APPLIED AT CHECKOUT AFTER ADDING INFORMATION FOR SIX OR MORE RIDERS. Not valid for Virtual Riders or combinable with other discounts.

    Registering from out of town and need a place to stay? Check out Discover Monona for all your lodging needs.

    *Loop the Lake is a rain or shine event, your registration is considered a donation and is non-refundable

    43.1 km from Town of Blue Mounds
    Madison, Wisconsin, 53714, United States
    OpenStreetMap Google Maps

    Cycling Virtual

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