Gravel & cycling events in Vermont

12 upcoming events in Vermont: gravel rides and races, road events, mountain bike and cyclocross.

November 2026

Unrouted

MTBGravelRoad

November 1, 2026Registration Open

Jericho, VT

40 / 75 mi · $35 · 4 registered

The 35th Annual West Hill Shop Cyclocross Race (RVCX Series #5)

GravelCX

November 7, 2026Registration Open

Putney, VT

49 registered

Annual Spicy Twicy Enduro Race

MTB

November 7, 2026Registration Open

Lyndonville, VT

3 registered

The Dirt

Gravel

November 8, 2026Registration Open

Waterbury Village Historic District, VT

31 / 42 mi · $45 · 48 registered

May 2027

The Dandy 2027

GravelRoad

May 22, 2027Registration Open

Derby, VT

26 mi · $75

Crazy 8 - Gravel Hundo - 14,500 Vertical

Gravel

May 23, 2027Registration Open

Ripton, VT

108 mi · $80 · 2 registered

Crazy 8 - 150 Miles - 15,000 Vertical

Road

May 23, 2027Registration Open

Ripton, VT

150 mi · $88

June 2027

The 2027 Black River Grand Prix & Epic

MTB

June 19, 2027Registration Open

Craftsbury, VT

16 / 31 mi · $35–$80

July 2027

XC Race Series presented by Stratton Bike Park ***POSTPONED****

MTB

July 21, 2027Opens 7/10/2027

South Londonderry, VT

September 2027

Peacham Fall Fondo

Gravel

September 25, 2027Opens 3/21/2027

Peacham, VT

50 mi · $99

October 2027

Vermont Rare Gravel Ride

Gravel

October 2, 2027Opens 2/28/2027

Peru, VT

45 mi · $20–$80

Fly to Pie 2027

Gravel

October 2, 2027Registration Open

Coventry, VT

6.2 / 14 / 17 / 26 mi · $50–$75