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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

NH Motor Speedway 2025 Bike Racing Series 7/17

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New England's favorite Thursday night racing series is back at New Hampshire Motor Speedway.

New racers are always welcome.  If you are a new racer and/or it is your first time at the series, please feel free to contact the race director with any questions or ask for assistance during registration.  The race series is a welcoming environment, and there are many experienced racers at the series who are happy to assist new racers. 

Mount Greylock Century

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Registration is now open for the 2025 Mt. Greylock Century!

Join us on Saturday, July 26th for this year’s edition, starting from the Stationery Factory in Dalton, MA. There's plenty of time to build up those miles before tackling the now legendary course that features over 12,000 feet of climbing. The Metric Plus route features 7,800 feet of climbing over 78 miles. 

Gravel Gallop for Okemo Mountain School

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Please join OMS for the Gravel Gallop bike ride on July 27. Riders can start at 8:30 am, but feel free to arrive at your convenience. 

We have 3 route options: 9 mile, 32 mile, and 45 mile loops, all through beautiful Plymouth, VT. The routes have great diversity and some challenging climbs. The start and finish will be at Plymouth State Park. The registration fee includes day use of the park for the whole day. Perfect for swimming in the lake after the ride!

Cycle-Smart Cyclocross Camp

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Cyclocross Camp — Cycle-Smart

The Cycle-Smart Cyclocross Camp is the original, most popular, and most emulated 'cross camp in North America. The camp's unique attraction lies in its beautiful setting, fun atmosphere, mix of ability levels and personalities, and the opportunity to learn and practice skills with America's best and most experienced 'cross coaches and racers.

Pan-Mass Challenge

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There’s A Lot Riding On Us

The PMC's mission is to raise funds for cancer research and treatment at Dana-Farber Cancer Institute. 100% of every rider-raised dollar goes directly to Dana-Farber.

The Ride

On August 2 & 3, 2025, the PMC community will come together from all corners of the world with one mission: raise funds for cancer research and treatment at Dana-Farber Cancer Institute. Together, we will get closer by the mile to a world without cancer. This is what a bike is meant to do.

24 Hours of Great Glen

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The magic of this race is the vibe. It’s about the encouragement from your fellow 500 riders. High fives, cheers, support from strangers, heartache, victory, and sore legs. It’s about perseverance, costumes, the music, the quiet riding at night, the beer, the party, bacon lap, the grilled cheese, the campground scene … come live the experience and become part of the history here at the Glen. 

Mt. Ascutney Bicycle Hillclimb

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Join us for an ascent up one of the USA’s most iconic climbs! The race takes place on a scenic state park road that’s completely closed to traffic. Compete head to head against some of the finest hill climbers on the east coast, or challenge yourself to conquer one of the hardest hills in the country. 

Our partner is once again the Ascutney Trails Association non-profit and all proceeds from the event will go to their important work developing trails for public use on Mt. Ascutney.

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Kearsarge Klassic

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The Kearsarge Klassic is, indeed, a gravel riding classic!

Launched by NHCC in 2012 the reins were turned over to GRVL Cycling in 2019. Ride HQ is in the the quaint village of Warner NH and includes many of the roads legacy riders have come to love.

Mt. Kearsarge Hillclimb

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The Mt. Kearsarge Hill Climb is an approx 8 mile climb up Kearsarge Mountain Rd.  onto the Mt. Kearsarge access road with a finish at the summit parking lot (elev. 2,937 ft).  The first 4.5 miles  is on a public road and includes some uphill, level, and downhill sections! The access road is 3.5 miles with an average grade of 8.7% and 1,738 feet in elevation gain.   When you reach the top, you'll be rewarded with a bare rock summit where, on a clear day, you can see as far as Boston and to the mountains in southern Vermont.

Mount Washington Hillclimb

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On Saturday, August 16, 2025, riders will race to the summit of Mt. Washington in what's been called, "the toughest hillclimb in the US, if not the world", the Mt. Washington Auto Road Bicycle Hillclimb (MWARBH). This race is hosted and benefits Tin Mountain Conservation Center.

TIMELINE: 
March 1st: MWARBHRegistration Opens
April 1st: Early Bird / Practice Ride Registration Opens 
July 13: Practice Ride
August 16 (17th raindate): MWARBH

Woodstock Triple Crown Throwdown

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We are offering a new event this year: a single day XC mountain bike stage race. Each of our trail networks will have a XC race stage on nearly 100% single track with chipped timing.  Win a stage or win the overall GC with lowest combined time. There will be enduro segments as well for good measure. Food and beverage by Ranch Camp included in registration fee. All proceeds go to building and maintaining the local trails. Get your legs race ready for the Overland the following weekend. Course will be approximately 38 miles total with 5000’ of climbing.

Race To The Top Of Vermont

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Every August the Delta Dental 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.

Vermont Overland

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The Overland is a 55-mile (distances fluctuate based on years/course) dirt road bicycle ride featuring close to 7,000 feet of climbing, eight sectors of Class4 Roads (unmaintained ancient public through-ways), two sag stops, a magnificently scenic route and an awesome party afterwards. It’s the ultimate overland adventure ride. Open dirt roads, amazing scenery and an epic course unlike any you’ve ever ridden before, all within a beautiful Vermont pastoral setting.

Green Mountain Stage Race

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Thank you for your interest in the Green Mountain Stage Race. In 2023 the GMSR was the largest stage race in North America! Velo has selected the GMSR as one of the top ten stage races in the US two years in a row! Come experience what it is like to be treated like a Pro regardless of your catagory. This will be the twenty-third edition of the GMSR! We hope you can join us.

Racers must be a Cat. 4 or higher to enter all stage race events except the Women's 3/4/Novice and Mad River Open Road Race. 

Finding Flow on the Trail @ ORO, Montpelier, VT

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This exciting NEW mountain bike skills clinic is all about finding more FLOW on the trails! Do you feel clunky riding around berms? Do you have trouble keeping up with your pals through rhythm sections? Do you want to gain more speed on the trails and have a more cohesive ride? Then this clinic is for YOU! The skills we’ll cover are geared toward the intermediate rider. We’ll gather tools around pumping technique and cornering technique, helping you gain more confidence and find your FLOW!

TriQuest Gravel Triathlon @ Ludlow, VT

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TriQuest is the new breed of triathlon incorporating the spirit of gravel and trail running to bring multisport to a new dimension.

Participants should note that the bike and run course times will be slower due to gravel & trail conditions and consider training for the same duration as a fast 70.3 triathlon.  

The course distances are:

  • 1 Mile Swim
  • 28 Mile Gravel bike
  • 8 mile Trail Run

Come join our inaugural event in central Vermont, September 6, 2025.

USAT Accredited

UVTA Tour de Taste 9/7

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Like to eat? Like to ride?
Join us for the Tour de Taste – a scenic, pedaling picnic through the Connecticut River Valley!

Bring your bike and enjoy autumn’s vibrant foliage at your own pace. Along the way, you’ll meet local food producers and community members at various tasting stops, featuring a delicious harvest bounty from nearby farms and restaurants. The event starts and finishes at Samuel Morey Elementary School in Fairlee VT.   Pre-registration is required.

Choose from three thoughtfully planned routes:

Cabot Ride the Ridges

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Cabot Ride the Ridges is a collection of great rides, runs, walks, and community enthusiasts. Register for a ride that best fits you, start at the Cabot Common, and witness our beautiful Vermont scenery.  100k, 60k, 30k, and family ride options.

All proceeds benefit the Cabot Mentoring program, a community organization dedicated to the development of Cabot youth. 

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PeterB says:  One of my favorite events for non-racers.  Very low-key, beautiful routes.

Tour de Creemee

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Most longtime Vermont cyclists have heard of the Central Vermont Cycling Tour, Vermont's original, classic gravel grinder ride. We're thrilled to announce that the host of this ride, the wonderful folks at Cross Vermont Trail Association, have just passed the baton to Onion River Outdoors!

Jumping 101 @ ORO, Montpelier, VT

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Join Christsonthy, a PMBIA Level 2 AIR certified Instructor, MTB skills coach and owner of Blue Sky MTB for a morning of learning to JUMP! Have you ever wanted to safely and confidently get your wheels off the ground? Do you feel like you’ve gotten all sorts of advice, but nothing is working? Do you struggle with getting in the air consistently?

VT 50

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The 32nd Vermont 50 Race will be held on September 28, 2025
Race Registration Opens on May 25, 2025 at 7 PM ET
Location: Base Camp-451 Ski Tow RD, West Windsor, Vermont
Race Weekend Schedule:
Saturday, Sept. 27 noon-7 PM-Bib/Bike Plaque Pick up, Vendor Fair, Kids Races 
Sunday, Sept. 28-Mandatory Race Meetings 5:30 AM for ALL 50 Mile; 7:30 AM for 50K
Race Waves Start at 6:10 AM  ( near Ascutney Outdoors Lodge)

Vermont Rare Gravel Ride @ Peru, VT

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Year 11~ We're Back ~Vermont Rare Gravel!

Glad to have you back for another year!  You'll see some new, some old and somewhere in between.  Keeping it around 40miles this year….but we're turning up the climbing on a few new roads.  

Why not #vermontraregravelride this Year?

"Grassroots GRavel" at its Finest!

It's not a Race, It's an Adventure!  

The Hidden Gem of Southern VT

Use your GPS - minimal signage

Start/Finish and post ride gathering at Wild Wings XC ski center

HBRN8R 6.0 @ West Burke, VT

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Our last 2-day weekend was so popular we are bringing it back with gravels on Saturday & a fully charged MTB race on Sunday!  Saturday features our 50k , 100k, & 100k+ mixed terrain gravel course options (NOT A RACE), which are nothing to sneeze at and fully marked/gps'd.  Sunday will feature our fully flagged 50 mile mountain bike race (strict limit of 200 riders) looping the best of what Kingdom Trails and surrounding area has to offer.