Gravel & cycling events in Wisconsin

21 upcoming events in Wisconsin: gravel rides and races, road events, mountain bike and cyclocross.

October 2026

High Plains Shootout Race 3 Hudson, WI

CX

October 31, 2026Registration Open

Hudson, WI

10 registered

Cross Fire

CX

October 31, 2026Registration Open

Sun Prairie, WI

15 registered

November 2026

Stump Farm Mountain Bike Races

MTB

November 1, 2026Registration Open

Suamico, WI

7 / 20 mi · $30–$50 · 50 registered

Kern Park Kross

CX

November 7, 2026Registration Open

Milwaukee, WI

19 registered

Sheboygan County Cycling Classic 2026

CX

November 8, 2026Registration Open

Sheboygan Falls, WI

2 registered

Kringle Kross-Midwest Regional CX Championships

CX

November 14, 2026Registration Open

Waukesha, WI

2 registered

Wisconsin State Cyclocross Championships 2026

CX

November 21, 2026Registration Open

Waterloo, WI

2 registered

January 2027

Snow Crown Series

RoadMTB

January 9, 2027Opens 11/29/2026

Suamico, WI

March 2027

Madison Shamrock Shuffle

Road

March 13, 2027Registration Open

Madison, WI

6.2 mi · $35

May 2027

The Bear 100

Gravel

May 1, 2027Opens 1/1/2027

Laona, WI

18 / 31 / 61 / 103 mi · $0–$69

Hungry Bear Gravel

Gravel

May 8, 2027Registration Open

Cable, WI

28 / 60 / 100 mi · $49 · 70 registered

June 2027

Gordon Pine Barrens 50

Gravel

June 5, 2027Registration Open

Gordon, WI

25 / 50 mi · $45 · 8 registered

Refo24

MTB

June 12, 2027Opens 1/1/2027

Suamico, WI

Horribly Hilly Hundreds

Road

June 19, 2027Opens 2/6/2027

Blue Mounds, WI

Loop the Lake - A bike ride to benefit our lakes

Road

June 19, 2027Registration Open

Madison, WI

July 2027

Catfish Days 50 Bike Tour

Road

July 10, 2027Opens 11/1/2026

Trempealeau, WI

50 mi · $30–$50

Dairyland Dare Presented by Incredible Bank

Road

July 31, 2027Opens 11/27/2026

Dodgeville, WI

31 / 62 / 93 / 124 mi · $95–$110

Pedal The Peace Rides

Road

July 31, 2027Registration Open

Afton, WI

9 / 25 / 50 mi · $15

Loon Ride at Mercer Bike Fest

Road

July 31, 2027Opens 12/23/2026

Mercer, WI

7 / 24 / 50 mi · $55

August 2027

Big Bull Falls Grand Fondo

Road

August 28, 2027Opens 12/3/2026

Wausau, WI

35 / 73 / 101 mi · $50

September 2027

Fall Color Festival

MTB

September 25, 2027Opens 2/28/2027

Whitewater, WI

5 / 13 / 18 / 31 mi · $25–$35