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Regional Cycling Events

This is a list of regional cycling events. Many of the events are based around gravel roads in VT and NH and have a variety of routes accommodating all skill levels. The courses vary from 16 miles to 50+ miles and can be smooth gravel or challenging class 4/6 roads with significant elevation changes. The Prouty is the exception as it includes road-only courses varying between 20 and 200 miles!

For more events, try the events calendar at BikeReg:  BikeReg.com - online cycling event registration

Winterbike 2026 - Burke, VT

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Mountain Bike Vermont and Kingdom Trails have partnered again for Vermont's favorite fatbike fest!

Join us Saturday, February 7th in East Burke, VT! Presented by Lawson's Finest Liquids, Winterbike is Vermont’s premier Fatbike Festival! Now in its 14th year, the event continues to be the favorite among fatbike enthusiasts. The event is headquartered at Mike's Tiki Bar and hosted on the Kingdom Trails network, boasting miles and miles of cold-rolled singletrack!

Widestock Fatbike Rodeo - Woodstock, VT

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Join Mountain Bike Vermont and Woodstock Area MTB Association (WAMBA) for our second annual fatbike fest in Woodstock, Vermont!

Presented by the Woodstock Area Mountain Bike Association, von Trapp Brewing, Ranch Camp, and Mountain Bike Vermont, we're proud to bring you Woodstock's second annual fatbike festival!

Join us Saturday, Frebruary 28th, 2026 for a day of fatbiking, feasting, and hearty brews around warm fires.

Pavement Ends gravel race 2026 - Henniker, NH

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State 9 Racing presents to you the Pavement Ends gravel bike race and ride.

Registration includes post race meal inside the Pats Peak Ski Area lodge, professional timing, an awesome marked course and a hell of a good time. 

Course will be revealed as we get closer to the race. Expect 40-50 miles of gravel and some class VI roads. Expect 4,000' or more elevation.

We've added Pavement Ends light. This category is geared towards those that may not have trained as much as they would have liked to over the winter or those that are new to gravel.  

Massochista 2026 - Ashfield, MA

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The Massochistah is a challenging recreational gravel ride to raise money for youth and adaptive cycling.

We are completely volunteer-run to maximize our support for the expansion and growth of cycling for all people. 

Location: Coming soon…

Lodging:  Coming soon…

Parking: Coming soon…

Historic Routes, But Stay Tuned For Updates: 

Crank the Kanc Hillclimb 2026 - Conway, NH

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Crank the Kanc :: Mount Washington Valley Bicycling Club

The annual Crank the Kanc bicycle time trial hill climb takes place each May on the beautiful
Kancamaugus Highway- a Scenic New Hampshire Biway through the White Mountain National Forest.
This time-trial hill climb race is approx 21.3 miles with 2340 ft. net elevation gain. (+2426 ft./-86 ft.)

The Dandy 2026 - Derby, VT

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Last year we added bikes to our Dandelion Run held on gravel roads through the world-famous Dandelion Fields of Derby, Holland, and Morgan.  It was such a hit that we are bringing it back for another year and inviting runners to join us on the full marathon distance.  It is hilly, challenging, and spectacularly beautiful.  The course is sprinkled with musicians.  So if you're not a racer, but more of a wanderer, you can stop along the way and hear some wonderful music.  Fees include a lunch after the event at the Derby Beach House.

Bikes for Bovines MTB race - Keene, NH

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We are excited to bring back the Bikes for Bovines Mountain Bike Race.  The race will be once again held at Stonewall Farm in Keene, NH with the opportunity to show off this great venue.  This is a great family and spectator friendly race with proceeds supporting the Keene High School Nordic Ski Team Booster Club and Stonewall Farm.    

The Ranger - Tunbridge, VT

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GRAVEL ADVENTURE FOR EVERYONE

The Ranger offers multiple ride distances and a gravel-enduro format, so while it’s not a race, there’s competition available for those seeking it. Sunday’s ride options include a 5-mile family/Junior Ranger; an 18-mile course with a community no-drop group-ride option; a 40-mile gravel enduro; and a 60-mile gravel century.

Raid Rockingham - Newmarket, NH

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Raid Rockingham Gravel Event, Newmarket, NH — GRVL Cycling

Are you are looking for a cycling challenge, a great ride with friends and an opportunity to kick back afterward to swap stories?

Well, we have the ride for you. Raid Rockingham combines elements of the area’s best roads on a supported course, with a great party awaiting you at the finish. Our post-ride party is legendary - there will be craft beer on tap and some tasty grub to match. 

CCNS 200on100 - Troy, VT

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Join us for a bucket-list one-day ride down Vermont’s legendary Route 100, tracing the entire length of the state from the Canadian border to the Massachusetts line. Soak in pristine New England scenery as you take on this iconic double-century adventure, fully supported by CCNS coaches and athletes every mile of the way.

Let us take care of everything.
All you have to do is show up ready to ride.


What to Expect
 

Class VI Classic 5.0 - Hanover, NH

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The fifth annual Class VI Classic contains some of the finest class VI roads in and around Etna, NH. Some of these roads are well maintained and frequently traveled, others... not so much. While some of the ride could be mistaken for a pleasant gravel grinder, other parts are unspeakably heinous and simply unrideable. Knowing when it's faster to dismount and walk is a necessary skill to finish the ride. The first year had no finishers (out of seven riders).

Prouty Ultimate

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The Prouty™ began in 1982 when four Cancer Center nurses, inspired by the courage of their patient, Audrey Prouty, committed to cycling 100 miles through the White Mountains of New Hampshire.

The annual 2-day Prouty Ultimate is an unparalleled ride experience honoring the origin of the event: two days of scenic and fully supported riding through the beautiful New England countryside, meals, and camaraderie. This is the Prouty at its best!

Prouty Ultimate takes place on July 10 & 11 in Hanover, NH.

The Prouty

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The Prouty is northern New England’s largest family–friendly fundraising event benefiting Dartmouth Cancer Center–where thousands of cyclists, walkers, rowers, golfers, tennis players, volunteers, and supporters unite for one powerful mission: to end cancer.

The Prouty started in 1982 after four Dartmouth Cancer Center nurses, inspired by their cancer patient Audrey Prouty, rode 100 miles through the White Mountains to honor her journey and raise money for others facing the same battle.

Raid Lamoille - Craftsbury, VT

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Raid Lamoille Vermont Gravel Event — GRVL Cycling

Lamoille - say it like a local, "lah-moyl" - rhymes with olive oil. Got it?

This ride is hosted out of the Craftsbury Outdoor Center in lovely Craftsbury, Vermont. Since 2012 Raid Lamoille has traversed some of the most sublime gravel in the Northeast. Combine that with an incredible after party and this is one ride you won't want to miss. 

24 Hours of Great Glen - Gorham, NH

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BIG DAY Brewing - 24 Hours | Great Glen Trails Outdoor Center

CELEBRATING 26 YEARS | AUGUST 1-2, 2026

Big Day Brewing 24 Hours of Great Glen, the most beloved and iconic mountain bike race in New England, returns again in 2026. This year, we’re going back to prehistoric times, camping, parties, kids events, live music and bash celebrating the most delicious suds around made by Big Day Brewing.

Eastern Grind XC MTB Race - Stowe, VT

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This is a EFTA (Eastern Fat Tire Association) Event - No License is Required.

We're excited to Host the 2026 Eastern Grind Race at Trapps Family Lodge in Stowe Vermont.  The event will consist of a 1 or 2 lap race that will feature tons of Singletrack mixed with just enough double track. Course is ~11.5 miles long/ ~1500ft of Climbing per lap

This a fundraiser for the Bicycle Express Junior Team.  Race to be held rain or shine - cancellations dependent on severe weather or trail conditions. Sorry No Refunds

Mt. Washington Auto Road bicycle hillclimb - Gorham, NH

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We are excited to return to the “rock pile” for the 53st Mt. Washington Auto Road Bicycle Hillclimb (MWARBH) presented by Tin Mountain Conservation Center! Tin Mountain Conservation Center is a non profit which provides opportunities to experience nature as the ultimate classroom.

In fact, this summer you have two opportunities to pedal to the top of Mt. Washington!  These event notes are for the main event, the supported, timed, exciting, and not-to-miss festival.

D2R2 2026 - Greenfield, MA

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The Deerfield Dirt-Road Randonnee was conceived in the 1990's as just a favorite dirt-road loop in the hilltowns of Franklin County, Massachusetts.  Since its birth as an organized event in 2005, many have hailed D2R2 as the hardest, most beautiful, most fun, most traffic-free, most unique, and overall best ride that they have ever done. However, D2R2 will continue to maintain its original character as just a bike ride –

Race to the Top of Vermont - Stowe, VT

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Every August, the Race to the Top of Vermont draws hikers, bikers, and runners from across the U.S. and Canada to climb Mt. Mansfield, Vermont’s highest peak. Our course ascends the historic Mansfield Toll Road – 4.3 miles in length and 2,564 feet of up! For some, it’s all about trying to achieve a fast time on this challenging course.

Cabot Ride the Ridges 2026 - Cabot, VT

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Cabot Ride the Ridges 2026 marks Year 13 of this fantastic gravel grinder, with each and every year better than the last. For returning riders, we continue to have the features that make our event Cabot RTR-special - 4 different gravel distances, beautiful views, friendly volunteers with positive attitudes, wood-fired pizza as the post-ride meal, lots of well-stocked aide stations, laughs, fun, and all to support a great cause.  We will continue to have Cabot RTR merchandise available for pre-sale, as well as day-of purchase (supplies may be limited).

Fly to Pie 2026 - Coventry, VT

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Fly to Pie is run on largely dirt roads through "the gut" of the Northeast Kingdom of Vermont,  26.2, 17. 13.5 and 6.2 mile options.  We schedule it during our Fall Foliage Season.  It is a running and a biking event.  We start at the Airport in Coventry and end at Parker Pie in West Glover with all the pizza you can eat and with a cash bar with Hill Farmstead bear on tap.  The primary biker route is 26.2 miles 

Marathoners start at the airport at 11:30 am

13.5 mile family challengers start at the airport at 10:30 am