Regional Cycling Events

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. 

This marks the 253rd* year of the Massochistah, and after last year's abrupt cancellation due to a freak snowstorm that rendered most of the hill towns unreachable and without power... WE ARE BACK. AND READY.

This ride is intended to be a great day of training for those headed to Unbound and other early-season gravel events. It's also a terrific ride in terms of great terrain and a big day in the saddle; one can enjoy this for what it is (a big day of awesome gravel and mixed terrain) or use it specifically as training to put final touches on an Unbound training plan prior to tapering for the big event.

Mixed terrain race & gran fondo with overall & age group awards

61 miles, 45 miles, 23 miles 
20% dirt roads
Direct passes through the villages and hamlets of Southern Washington County, NY 
Registration includes:

Moto & sag support 

On-course mechanical support

2026 Course maps (PENDING)

Course signage 

Police controlled intersections

Chip timing & results

Personalized bib numbers if registered by April 1, 2026

Every Tuesday night. We close the shop doors at 5:30pm, so depending on the ride location, we aim to be riding by 6:15. All ability levels are welcome to join and it's a no-drop ride. If you'd like to join us please send us an email at info@omerandbobs.com and we will add you to our mtb ride email list.  

Some of our favorite places to ride...

Union Village Dam - Thetford, VT 

The Coös Frost Heave is a 15.5 mi (Short Course) or 27.5 mi loop (Full Course) starting in Jericho State Park and extending through scenic Berlin, NH. The best bike for the loop is rider's choice, the best cyclist for the loop is…definitely you. 

The Bike Hub is proud to announce our Sunday Epic ride series! These are all-day rides featuring some of the best mixed-terrain riding the tri-state area has to offer. Forgotten woods roads, fast gravel, rugged singletrack, and even a bit of hike-a-bike. These rides will be long, difficult, and absolutely beautiful. While there is no perfect bike for a Sunday Epic, anything with around a 2 inch tire will work. More details on terrain will be included in each event post. Sunday Epic's will be held the third Sunday of every month from April-September.

Race will start at 6 a.m. sharp.  Course closes at midnight.  

The course is 108 miles and features very challenging terrain, with a total of 14,500 feet of climbing.

The course is 78% unpaved.

Ride with GPS - https://ridewithgps.com/routes/50534057

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.

Race will start at 6 a.m. sharp.  Course closes at midnight.  

The course is 150 miles and features 8 mountain gaps with a total of 15,000 feet of climbing.

The course is 80% paved.

Ride with GPS - https://ridewithgps.com/routes/50318224

In its fourth year, Elevate will offer three days of clinics, group rides, socials, bike demos, and much more. Registration for this historically sold out event opens February 3rd, 2026 at 8:00am.

Review our Pre-Registration document for key details to know before registering.

Dirt roads. Farm stops. Barn dance.
 Welcome to year five of Vermont’s most community-driven gravel celebration — proudly supporting our local towns and the backroads that connect them.

Your day starts with strong coffee at our wedding-barn-turned-gravel-HQ, tucked into 1,000 acres of pure Vermont countryside. From there, you’ll roll out onto classic dirt roads (yes, a few spicy Class IVs), winding past working farms (where animals await you), mountain views, and the kind of quiet that makes you fall in love with riding all over again.

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.    

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.

Help take care of this wonderful 423-acre community gem!  Clear downed trees, drainage and treadway work.  Bring water, gloves, boots, tick & eye protection.

Cookout to follow.

Directions: Take Rt. 4 to Center of Town road. Turn onto Kings Highway. Turn right onto Reservoir Road. Go 1/2 mile to the Trailhead parking area.

For more information, contact Town Planner Matt Osborn at 802-478-1118

mosborn@hartford-vt.org

Hartford Conservation Comission

The 8th annual Analog 4x4 features 3 ride options for ‘26.  There's the classic 40 miler, with the rocky class 4 roads and the hike a bikes, but we're also introducing the 2x4 (25ish miles, two class 4 roads, over 2500' less climbing) and the 1x4 for folks who just wanna sample platter: a bit of rail trail, a bit of dirt road, a singular class 4 road. 

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. 

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
 

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).

The 2026 Dirty Project is on Saturday, June 27

We'll be live and in-person starting from Norwich Green, 22 Church St, Norwich, VT 05055. The finish is right up the street  at the Norwich Inn, 325 Main St, Norwich, VT 05055. We are capping the field at 200 riders, so sign up early! Our registration fee is $100, with one hundred percent going to The Prouty as a donation!

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 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.

General Event Information

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. 

The north east is an amazing backdrop for XC MTB racing…. We have the mountains, we have the dirt, the forest cover and a dense population with thousands of passionate cyclists. What we don’t have is a consistent XC series or a unified cross country racing community. As a veteran promoter and a dedicated racer, that is a challenge that has intrigued me for years. I am proud and ready to accept that challenge. 

Bike Ride | Middletown | Tour-de-slate

The Tour de Slate 'ride to end addiction' is a bicycle ride that raises funds for Adult and Teen Challenge Vt. The rides are centered in and around Middletown Springs, Vt. and the neighboring towns. 

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.

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

The Kearsarge Klassic is, indeed, a gravel riding classic. Launched in 2012 the reins were handed over to GRVL Cycling in 2019. Now based out of the quaint town of Warner NH the ride includes many of the same roads legacy riders have come to love.

The Highs & Lows Tour is a one-day cycling event featuring a variety of routes designed to showcase the natural beauty and terrain of New Hampshire. Riders can choose from traditional road routes, mixed-surface gravel adventures, and—new for 2026—a mountain biking option that opens up even more ways to explore.

The north east is an amazing backdrop for XC MTB racing…. We have the mountains, we have the dirt, the forest cover and a dense population with thousands of passionate cyclists. What we don’t have is a consistent XC series or a unified cross country racing community. As a veteran promoter and a dedicated racer, that is a challenge that has intrigued me for years. I am proud and ready to accept that challenge. 

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.

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.

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 –

Vermont’s premier Cross-Country and Enduro stage race is BACK! With the amazing success of our inaugural Woodstock Triple Crown Throwdown last summer, we are bringing back this fundraiser that supports the Woodstock Area Mountain Bike Association (WAMBA)! This event is truly one-of-a-kind, featuring some of the best riding in Vermont! The Triple Crown Throwdown is an unparalleled adventure to support our amazing trails and to test your endurance. One day, three networks, three XC “Superstages”, 4-6 Enduro “Substages,” food and beer included, and all-day stoke and good times.

The 11th Annual Rose Mountain Rumble (RMR) takes place Saturday, August 29th, 2026. 

Registration opens 7:00 AM, rolling starts begin 7:30 AM.

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.

We are excited to announce that we are planning to host two half-day clinics for adults who are interested in learning more about mountain biking. The clinics will run from 9 am to 12 pm with lots of hands-on learning led by Stuart Lander, our Gear Shifters leader. There will be options for a trail ride experience to work on new skills!

If interested in attending the half-day clinics, please register online at LebanonNH.gov/Register or by clicking below.

Fall Clinic – September 5th from 9 am to 12 pm at the Landmark Trails

Celebrate the 21st Annual Kelly Brush Ride on Saturday, September 12, in Middlebury, Vermont. Traverse the beautiful Champlain Valley on one of six different routes and end your ride with live entertainment, delicious BBQ, cold beverages, and family fun at Middlebury College.

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).

What is the Vermont Super 8 Grand Depart?​

It's a self-supported bikepacking adventure that takes place at the end of September. Most riders start and finish in Montpelier. The course is self-navigated using GPS devices. Riders are provided with a route and a list of resources, but they otherwise must carry their own gear and make their own camping arrangements. The course features some of Vermont's extremely rugged roads and trails, and it covers very hilly terrain.

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"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

 Vermont Rare

What to Expect 

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

2026 marks the 39th Anniversary of the Great River Ride. Over the years the GRR has been recognized by the League of American Bicyclists (LAB) and Bicycling Magazine as one of the top century rides in America. A variety of routes are offered to match the skill levels of all participants. Event proceeds will benefit the programs of the Friends of the Columbia Greenway Rail Trail (FOCGRT), a 501 3c nonprofit organization.  

Staffed refreshment stops along the ride as well as a post-ride buffet with live entertainment from 2:00 PM to 5:30 PM. 

Race on the Northeast Kingdom's "wild side” in this reincarnation of the popular CircumBurke race (2010-2018).  Our club is not a commercial race promoter. 100% of proceeds are reinvested in trail maintenance on Victory Hill.   

Welcome to the 11th Annual Keene Pumpkin Cyclocross Race on Sunday, October 5th.  The event is held at the Surry Mountain Recreation Area just outside of Keene in Southwest NH.  The race is on Surry Mountain lake with beautiful  hillside vistas during what is typically peak foliage for the region.

The Dirt -Hosted by Bicycle Express- Bringing gravel riding back to reality - no podium….no timing….just riding a bike

49% of extremely biased twitteratti agree:  this race is basically the World Championships