Gravel & cycling events in Massachusetts

10 upcoming events in Massachusetts: gravel rides and races, road events, mountain bike and cyclocross.

October 2026

35th Annual Cycle-Smart Northampton Cyclocross

CX

October 30, 2026Registration Open

Northampton, MA

274 registered

November 2026

The Dirty Pilgrim

Gravel

November 1, 2026Registration Open

Plymouth, MA

24 / 34 / 42 mi · $15 · 142 registered

NCC Trail Blasters Youth Cyclocross Racing Team 2026

CX

November 8, 2026Registration Closed

Northampton, MA

42 registered

Secret Squirrel CX

MTBCX

November 21, 2026Registration Open

Raynham, MA

37 registered

December 2026

The Ice Weasels Cometh

CX

December 5, 2026Registration Open

Southwick, MA

56 registered

The Sandy Neck Fat Bike Winter Classic!

MTB

December 6, 2026Opens 10/31/2026

West Barnstable, MA

15 mi · $100

January 2027

Rhino Racing Winter Race

MTB

January 10, 2027Registration Open

Marshfield, MA

March 2027

Winterräden

MTB

March 7, 2027Registration Open

Uxbridge, MA

2 registered

June 2027

2027 Tour de Barnstable

Road

June 6, 2027Registration Open

Barnstable, MA

19 / 29 / 40 / 69 mi · $300 · 35 registered

Carolina Hill MTB Classic 2027

MTB

June 27, 2027Opens 4/1/2027

Marshfield, MA