Gravel & cycling events in the Midwest

120 upcoming events in the Midwest: gravel rides and races, road events, mountain bike and cyclocross.

November 2026

Roadrunner CX

Thu, Nov 5, 2026Closes Nov 5

Minneapolis, MN

O'Bannon Adventure Ride - It's a Mountain Bike Festival

Fri, Nov 6, 2026Open

Corydon, IN

165 registered

Bison or Bust! The Tertiary Trek: National Bison Day Ride to Midewin National Tallgrass Prairie

Gravel

Sat, Nov 7, 2026Open

Chicago, IL

43 / 76 / 93 / 125 mi · Free · 4 registered

Kern Park Kross

Sat, Nov 7, 2026Closes Nov 5

Milwaukee, WI

119 registered

The Route 66 Oreo Roubaix Gravel Ride

Gravel

Sat, Nov 7, 2026Open

St. Louis, MO

17 / 25 / 44 mi · $50 · 49 registered

NEOCX: Forest Hill Park Thunderdome CX

Sat, Nov 7, 2026Open

Cleveland Heights, OH

3.1 mi · $5 · 25 registered

Threat Level Midnight Endurance MTB Race Sponsored by Rah Law

Sat, Nov 7, 2026Open

Highlandville, MO

41 registered

The ArchMaker CX

Sat, Nov 7, 2026Closes Nov 6

Hiawatha, IA

62 registered

Groundhog PSI-Clocross Day 1 - 2026 ChiCrossCup #7

Sat, Nov 7, 2026Closes Nov 6

Woodstock, IL

86 registered

Muleskinner CX

Sat, Nov 7, 2026Open

Lone Jack, MO

33 registered

Sheboygan County Cycling Classic 2026

Sat, Nov 7, 2026Closes Nov 5

Sheboygan Falls, WI

40 registered

Iceman Cometh Challenge

Sat, Nov 7, 2026Open

Traverse City, MI

10 / 30 mi · $70–$140

Huntington Veterans Day 5K

Road

Sat, Nov 7, 2026Open

Huntington, IN

17 mi · $25

Riverside Rumble Cyclocross p/b Bishop’s Bicycles - OVCX Race #9

Sun, Nov 8, 2026Open

Milford, OH

129 registered

The Bubba Memorial Cyclocross Series Presented by The Cycling House

Sun, Nov 8, 2026Open

Richmond Heights, MO

250 registered

Groundhog PSI-Clocross Day 2 - 2026 ChiCrossCup #8

Sun, Nov 8, 2026Open

Woodstock, IL

101 registered

NEOCX: Series Finale

Sat, Nov 14, 2026Open

Cleveland, OH

3.1 mi · $5 · 4 registered

Spearhead CX

Sat, Nov 14, 2026Open

Fenton, MI

39 registered

Kringle Kross-Midwest Regional CX Championships

Sat, Nov 14, 2026Open

Waukesha, WI

5 registered

2026 MN State Cyclocross Championships

Sat, Nov 14, 2026Open

New Brighton, MN

30 registered

OVCX #10 - 2026 Treason Cross p/b Midwest NXT

Sat, Nov 14, 2026Open

Seymour, IN

26 registered

WIIL Assn-ABR 2026 Season Awards Party

Road

Sat, Nov 14, 2026Open

Barrington, IL

15 registered

OVCX #11 - Boiler Cross

Sun, Nov 15, 2026Open

Lafayette, IN

18 registered

Wisconsin State Cyclocross Championships 2026

Sat, Nov 21, 2026Open

Waterloo, WI

6 registered

Gravel Grovel

Gravel

Sat, Nov 21, 2026Open

Norman, IN

30 / 42 / 62 mi · $35–$85

Trees Trail Challenge

Sat, Nov 21, 2026Open

Fort Wayne, IN

10 / 20 mi · $40

Quarry Cross at The Forge - 2026 ChiCrossCup #9

Sun, Nov 22, 2026Open

Lemont, IL

27 registered

Straight Street Hill Climb

Road

Sun, Nov 22, 2026Open

Cincinnati, OH

0.4 mi · $17.50

December 2026

Rapture in Misery

Sat, Dec 5, 2026Open

Lee's Summit, MO

60 mi · $69 · 51 registered

Iowa State Cyclocross Championships

Sat, Dec 5, 2026Open

Altoona, IA

2 registered

Storm the Bluffs

Sat, Dec 5, 2026Open

Minnesota City, MN

9.3 mi · $45

Remember the Removal Walk, Ride, and Bike

Road

Sat, Dec 5, 2026Open

Steelville, MO

13 mi · $20–$35

The Keating Injury Law Montrose Beach CX - 2026 ChiCrossCup #10

Sun, Dec 6, 2026Open

Chicago, IL

29 registered

January 2027

Norpine Fat Bike Classic

Fri, Jan 8, 2027Open

Lutsen, MN

12 / 27 mi · $25–$90 · 23 registered

Snow Crown Series

Road
MTB

Sat, Jan 9, 2027Opens Nov 29

Suamico, WI

Triple D Winter Endurance Race

Sat, Jan 16, 2027Open

Dubuque, IA

26 / 31 / 35 / 70 mi +3 more · $35–$80 · 13 registered

Frozen Fat Fondo Fest 2027

Sat, Jan 30, 2027Open

Davenport, IA

3 registered

February 2027

City of Lakes Loppet Winter Festival

Sat, Feb 6, 2027Open

Minneapolis, MN

6.2 / 12 / 19 mi · $47–$68

Lake Macbride Fat Tire Classic

Sat, Feb 13, 2027Open

Solon, IA

15 / 30 mi · $0–$50 · 52 registered

Frozen Trailfest Trail Race

Sat, Feb 13, 2027Open

Fort Wayne, IN

12 mi · $30

The Abominable Snow Tri

Sun, Feb 21, 2027Open

Belmont, MI

6 mi · $50

March 2027

Michigan Off Road Championship MTB Race Series

Mon, Mar 1, 2027Opens Mar 1

Battle Creek, MI

Frozen Chain Gravel Classic

Gravel

Sat, Mar 13, 2027Open

Madison, IN

32 / 61 mi · 4,239 ft · $50 · 2 registered

Madison Shamrock Shuffle

Road

Sat, Mar 13, 2027Open

Madison, WI

6.2 mi · $35

Melting Mann Gravel Race - VOLUNTEERS

Gravel

Sat, Mar 20, 2027Open

Vandalia, MI

25 / 39 / 58 mi · 1,537 ft · $75–$100 · 83 registered

The Tour of St. Louis Omnium

Road

Sat, Mar 20, 2027Open

St.Louis, MO

11 mi · $0–$45 · 1 registered

Dirty 30 Gravel

Gravel

Sat, Mar 27, 2027Open

Saranac, MI

16 / 31 / 50 / 100 mi +2 more · $0–$87 · 98 registered

April 2027

Rough Road 100

Road

Sat, Apr 3, 2027

Morris, IL

40 / 62 mi · $75

Iowa Wind and Rock

Gravel

Sat, Apr 17, 2027Open

Winterset, IA

340 mi · Free · 84 registered

The Missouri OUTLAW Gravel Race

Gravel

Sat, Apr 17, 2027Open

St Genevieve, MO

45 mi · $59

Mohican Trail Jamboree 2027

Sun, Apr 18, 2027Open

Loudonville, OH

5.3 / 13 / 25 mi · Free

SHOW ME MO GRAVEL SERIES

Gravel

Sun, Apr 18, 2027Opens Dec 3

St Genevieve, MO

45 mi · $133

Coal Country Roubaix

Road
Gravel

Sat, Apr 24, 2027Open

Lisbon, OH

33 / 62 / 100 / 300 mi · $35–$125 · 15 registered

VeloScience Vintage Rally to support CHA Animal Shelter

Road

Sun, Apr 25, 2027Opens Dec 9

New Albany, OH

40 mi · $45

May 2027

The Bear 100

Gravel

Sat, May 1, 2027Opens Jan 1

Laona, WI

18 / 31 / 61 / 103 mi · $0–$69

The Steel Dynamics Garbage Mountain Gravel Grinder

Gravel

Sat, May 1, 2027Open

Terre Haute, IN

35 / 63 mi · $40

Mud, Sweat & Beers - The Lumberjack 17!!!

Road
MTB

Sat, May 1, 2027Opens Nov 30

Traverse City, MI

4 / 12 / 14 / 25 mi +1 more · $15–$70

Hungry Bear Gravel

Gravel

Sat, May 8, 2027Open

Cable, WI

28 / 60 / 100 mi · $49 · 73 registered

Calvins Challenge 2027

Road

Sat, May 15, 2027Open

Springfield, OH

7 / 16 / 50 / 100 mi · $45–$100

Custer’s Last Stand

Sat, May 15, 2027Opens Jan 1

Augusta, MI

7.5 / 15 / 23 mi · $45

White Squirrel Roubaix

Road

Sat, May 15, 2027Opens Jan 1

Olney, IL

12 / 31 / 62 mi · $30–$55

Red Eagle Gravel Grinder

Gravel

Sun, May 16, 2027Opens Jan 1

Geneva, OH

12 / 23 / 44 mi · $50

American Triple-T Multisport Festival

Road

Fri, May 21, 2027Open

Perrysville, OH

26 / 52 mi · $30–$40

2027 Mohican 100 Mile/100K/50K MTB Race OMBC

Sat, May 22, 2027Open

Loudonville, OH

31 / 62 / 100 mi · $80–$180 · 153 registered

Dr. John Seaman Memorial 5k Run/Walk/Bike

Road

Sat, May 29, 2027Opens Jan 29

Vicksburg, MI

12 mi · $40

KEJ: Gravel 2027

Gravel

Sat, May 29, 2027

McArthur, OH

11 / 20 / 37 mi

June 2027

Gordon Pine Barrens 50

Gravel

Sat, Jun 5, 2027Open

Gordon, WI

25 / 50 mi · $45 · 16 registered

Walk & Roll Chicago

Road

Sat, Jun 5, 2027Open

Chicago, IL

9.3 mi · $20

Fort4Fitness Spring Cycle

Road

Sat, Jun 5, 2027Opens Dec 29

Fort Wayne, IN

22 / 36 / 50 / 63 mi +1 more · $30–$35

MCMBA MILFORD BIKE FEST AND TRAIL CHALLENGE

Road

Sat, Jun 5, 2027Closed

Milford, MI

Happy Soles 5k Run/Walk/Bike & Virtual Challenge

Road

Sun, Jun 6, 2027Opens Dec 6

Taylor, MI

3.1 mi · $35

Refo24

Sat, Jun 12, 2027Opens Jan 1

Suamico, WI

Pedal Putnam 2027

Road

Sat, Jun 12, 2027Opens Nov 25

Greencastle, IN

13 / 43 / 62 mi · $30–$70

Cogs and Kegs

Road

Mon, Jun 14, 2027Opens Mar 19

Birmingham, MI

10 / 30 mi · $45–$55

2027 - National 24 Hour Cycling Challenge (N24HCC)

Road

Sat, Jun 19, 2027Open

Hastings, MI

2 registered

Horribly Hilly Hundreds

Road

Sat, Jun 19, 2027Opens Feb 6

Blue Mounds, WI

Loop the Lake - A bike ride to benefit our lakes

Road

Sat, Jun 19, 2027Open

Madison, WI

Pedal Across Lower Michigan (PALM)

Road

Sat, Jun 19, 2027Opens Jan 1

TBD, MI

325 mi · $210

Michigan's Coast to Coast Gravel Grinder 204-Miler & Coast Loop 100-Miler

Gravel

Sat, Jun 26, 2027Open

Au Gres (204 start) to Ludington (204 and 100 finish), MI

100 / 204 mi · $70–$190 · 93 registered

Tour de Chi

Road

Sat, Jun 26, 2027Open

Chicago, IL

150 mi · $30 · 1 registered

KeyBank Gran Fondo

Road

Sat, Jun 26, 2027Open

Grand Rapids, MI

8.9 / 20 / 38 / 81 mi · $49–$209

Flat 50 (Adams County, IN)

Road

Sat, Jun 26, 2027Opens Dec 16

Berne, IN

50 mi · $35

Lutsen 99er

MTB
Gravel

Sat, Jun 26, 2027Opens Dec 1

Lutsen, MN

31 / 47 / 60 / 97 mi · 5,105 ft

July 2027

The Cedar Blitz: Gravel War on Wheels

Gravel

Sat, Jul 10, 2027Open

Cedar Springs, MI

18 / 36 / 50 / 128 mi · $35–$100 · 4 registered

Freedhem Gravel

Gravel

Sat, Jul 10, 2027Opens Feb 1

Little Falls, MN

46 / 76 mi · $49–$59

Miner Tough Weekend

Sat, Jul 10, 2027Opens Jan 1

Park Hills, MO

1.2 / 5 / 9 / 13 mi · $0–$75

The Big Rub

Gravel

Sat, Jul 10, 2027Open

Sedalia, MO

16 / 31 / 62 mi · $35

Catfish Days 50 Bike Tour

Road

Sat, Jul 10, 2027Open

Trempealeau, WI

50 mi · $30–$50

Wreath's Across America: Ride to Remember

Road

Sat, Jul 10, 2027Open

Findlay, OH

Shelden's BIG Bang XC MTB Race

Sat, Jul 17, 2027Opens Feb 1

Utica, MI

8.5 / 17 / 26 mi · $45

Hot Summer Singletrack Trail Race

Sat, Jul 17, 2027Open

Fort Wayne, IN

30 / 60 mi · $30

Tour Da Yoop, Eh™ 2027

Road

Thu, Jul 22, 2027Open

Manistique, MI

600 / 720 / 840 / 960 mi +4 more · $245–$1960 · 26 registered

Dairyland Dare Presented by Incredible Bank

Road

Sat, Jul 31, 2027Opens Nov 27

Dodgeville, WI

31 / 62 / 93 / 124 mi · $95–$110

Pedal The Peace Rides

Road

Sat, Jul 31, 2027Open

Afton, WI

9 / 25 / 50 mi · $15

9th Annual Megan's Ride and Walk 2027 Benefiting Nine13sports

Road

Sat, Jul 31, 2027Opens Mar 14

Westfield, IN

20 / 50 mi · $35

Amishland and Lakes Weekend Bike Tour

Road

Sat, Jul 31, 2027Opens Jan 1

Lagrange, IN

Loon Ride at Mercer Bike Fest

Road

Sat, Jul 31, 2027Opens Dec 23

Mercer, WI

7 / 24 / 50 mi · $55

August 2027

Tour De Dickinson

Road
MTB

Sat, Aug 7, 2027Open

Iron Mountain, MI

18 / 20 / 40 / 62 mi +1 more · $20–$45

2026 Lake Antoine Classic

Road

Sat, Aug 14, 2027Opens Feb 14

Iron Mountain, MI

9.3 mi · $20

RAMBA Shenanigans

Fri, Aug 20, 2027Open

Ishpeming, MI

27 registered

Fast Fitty Gravel Road Race

Gravel

Sat, Aug 21, 2027Opens Jan 1

Charlotte, MI

19 / 36 / 54 mi · $50

Northwoods Stage Race

Wed, Aug 25, 2027Open

Cable, WI

Hancock Flat 50

Road

Sat, Aug 28, 2027Open

Greenfield, IN

25 / 50 mi · $59.99–$74.99

Tour de La Porte 2027

Road

Sat, Aug 28, 2027Opens Jan 1

La Porte, IN

Big Bull Falls Grand Fondo

Road

Sat, Aug 28, 2027Opens Dec 3

Wausau, WI

35 / 73 / 101 mi · $50

2027 Shawnee Pebble Pounder - Gravel Race & Adventure Ride / QCW Queen City Wheels

Gravel

Sun, Aug 29, 2027Opens Dec 25

West Portsmouth, OH

36 / 45 mi · $65–$110

September 2027

Firefly Trail Festival

Sat, Sep 4, 2027Open

Fort Wayne, IN

6.2 / 12 / 19 mi · $20

HMFA’s Tour de Heartland Fundraiser

Road

Sat, Sep 11, 2027Opens May 10

Greenview, IL

12 / 17 / 45 mi · $35–$45

PEDALS

Gravel
Road
MTB

Sun, Sep 12, 2027Opens Dec 31

Cannonsburg, MI

10 / 20 / 32 / 62 mi · $65

Dirtworx MTB Fest 2027

Fri, Sep 17, 2027Opens Jun 1

Findlay, IL

Marji Gesick

Fri, Sep 17, 2027Open

Ishpeming, MI

15 / 50 / 100 mi · $150–$195

Mora Bike Tour and GraveLoppet Race

Gravel
Road

Sat, Sep 18, 2027Open

Mora, MN

4.5 / 25 / 50 / 100 mi · $10–$50

Chequamegon MTB Festival

Sat, Sep 18, 2027Opens Dec 1

Hayward, WI

16 / 40 mi

IWP Ride Against Suicide 2027

Road

Wed, Sep 22, 2027Opens Jan 15

Forest Lake, MN

73 / 86 / 300 mi · $100

Fall Color Festival

Sat, Sep 25, 2027Opens Feb 28

Whitewater, WI

5 / 13 / 18 / 31 mi · $25–$35

October 2027

The Big Wild

Sat, Oct 2, 2027Open

Atlanta, MI

25 / 76 mi · $75–$95 · 49 registered

ROJR 2026

Road

Sat, Oct 2, 2027

Holmesville, OH

40 / 67 mi

Opal Wapoo Gravel

MTB
Gravel

Sat, Oct 9, 2027Opens Feb 7

Excelsior Springs, MO

20 / 30 / 45 / 85 mi · $30–$120

Walk. Run. Bike. for Remember Nhu.

Road

Sat, Oct 23, 2027Opens Nov 17

Warren, OH

15 / 30 / 50 mi · $40

2027 I Love Gravel Racing Points Series

Gravel

Sun, Oct 31, 2027Opens Nov 15

Garden City, MI