Gravel & cycling events in Massachusetts, October 2026

17 events in Massachusetts in October 2026.

2026 Greylock Go Around 50K Mountain Bike Fundraiser

MTB

October 3, 2026Past Event

Adams, MA

Berkshire Cross

CX

October 3, 2026Past Event

Great Barrington, MA

BOSSCROSS - Oct 3 - Westford, MA

CX

October 3, 2026Past Event

Westford, MA

King's Tour of the Quabbin

Gravel

October 4, 2026Past Event

Hardwick, MA

Great Pumpkin Smash

MTB

October 4, 2026Past Event

Westwood, MA

Fall Foliage Gravel Grinder (F2G2)

Gravel

October 4, 2026Past Event

Great Barrington, MA

South Beach CX #5

CX

October 6, 2026Past Event

Westwood, MA

Lancaster CX Festival - Lanterns & Legions p/b Midnight Ride & Minuteman CX

CX

October 10, 2026Past Event

Lancaster, MA

Great River Ride Century / Berkshire Brevets 2026

Gravel

October 11, 2026Past Event

Westfield, MA

South Beach CX #6

CX

October 13, 2026Past Event

Westwood, MA

Tree House CX

CX

October 16, 2026Past Event

South Deerfield, MA

Really Rad Festival of Cyclocross 2026

CX

October 23, 2026Past Event

Falmouth, MA

1000 mi · Free · 439 registered

Cycling-The Series + Partially Canceled

Gravel

October 24, 2026Past Event

West Yarmouth, MA

42 mi · $110 · 14 registered

Brutiful Cape: Gravel Bike & Fat Bike Adventure Rides - Oct 24 & 100 Miles for Fat Bikes Oct 25

Gravel

October 24, 2026Past Event

Eastham, MA

31 / 62 / 100 mi · $95 · 65 registered

Cider Cross

CX

October 25, 2026Past Event

Phillipston, MA

72 registered

NCF Batacular Bike Race 2026

Road

October 25, 2026Past Event

Nantucket, MA

35th Annual Cycle-Smart Northampton Cyclocross

CX

October 30, 2026Registration Open

Northampton, MA

274 registered