Regional Cycling Events

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 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. 

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.

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. 

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.

GREEN MOUNTAIN STAGE RACE – The largest stage race in North America in 2023

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-fifth edition of the GMSR! We hope you can join us.

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