2017 New England Dirt Road Events

March 26th Vermont Overland Maple Adventure Ride:
Reading, VT. Peter Volers has organized a spring dirt road ride for several years. This year he is inviting more folks to come up and enjoy the start of sugar season on Vermont dirt roads. 27 miles, 90%l dirt.

April 15th
 Greasy Joes Gravel Grind
West Greenwich, RI: early season dirt road event. 47 miles

April 22nd Rasputitsa
East Burke VT: The fine folks who put on the Dirty 40 last year are running a spring/mud season race again. This year the race will go through the challenging hills around Burke Mountain. Expect tough racing, interesting sag stops, and some hiking. 40 miles, 80% dirt road RACE! Sold Out!

April 29th The Muddy Onion
Montpelier VTVermont is now the heart of New England dirt road riding. I'm not entirely sure why, but there are a lot of great dirt roads & a bunch of bike nuts in the state. So here's another one, put on by the good crew at Onion River Sports. Low cost at $20 but limited to 100 riders. 32 miles 90% dirt.

April 29th Digression Ride
Sherborn, MA Same format as the popular RSC Diverged Ride. Breakfast, support, 3-4 hours of challenging mixed terrain riding. Start/end at Ride Head Quarters. 38 miles 50% dirt

May 6th Diverged Ride
Lexington MA. Last year the Ride Studio Cafe hosted this event to great reviews. I have a feeling this years ride will be much more. Overland Base Camp has taken over this & other past RSC events. A casual mixed terrain tour of the Boston 'burbs. Fast, medium, & casual pace groups self seeded. 38 miles 50% dirt. Breakfast before the ride at RSC.

May 7th Waterbury Gravel Grinder
Waterbury, VT A benefit ride for the Waterbury Area Trails Association.

May 13th NER Meshomasic
Hartford, CT. New England Randonneurs are branching into more mixed terrain rides. Expect brevet type support and an adventurous ramble through the dirt road offerings in eastern Connecticut. 73 miles 50% dirt?

May 13th Rhodekill Classic
West Warwick, RI. When is a ride a race? This may be one of the most competitive "non-competitive" events in New England. Designed as training for Battenkill, this course goes through the out of the way small towns in central RI & across 13 sections of dirt road. GU products & Narragansett beer at the end for replinshment, oh, and Hot Pie! 65 miles 35% dirt

May 20th: Westhampton Gravel Enduro
Westhampton, MA. A rugged single loop ride with 4 timed Strava segments for prizes & bragging rights. Post ride party with enchilada's & BYOB refreshments. 45 miles 90% dirt?

May 21st Farmer's Daughter Gravel Grinder
Chatam, NY. While this list is primarily New England dirt road events I am happy to include a few that are just outside the region. Here is a new one that Peter Volers recommended to me. 65 miles 75%+ dirt

May 20-21st Maneha 250
Lexington, MA: A new Overland Base Camp event, bike packing on mixed terrain from Lexington to NH and back the next day for a total of 250 miles! Sag support, meals, & campsite are included in the entry fee. Too many important details to list here, so read the ride description closely at the link above.

June 4th Raid Rockingham
Newmarket NH. Arlon puts on great events. Lately cycling events have become his passion. He is also the organizer behind Ted King's ride in October. 62 miles 45% dirt

June 4th Tour de Heifer
Brattleboro VT. This event supports local farms, so the ride is also fully supported with local food! 3 routes of 15, 30, & 60 miles. The course is a D2R2 lite (even using some of the same roads). 60 miles 80% dirt.

June 10th Neyoco
Westchester, CT New even from Overland Base, 62 miles

June 10th VT Monster Gravel Grinder:
Ludlow, VT: a new event at Okemo Mountain. A stiff 9000 feet of climbing, 70 mile route. Harpoon beer and b-b-que after the ride. Limited mechanical support and 2 stocked feed stations. 80% dirt

June 18th The Ranger
Tunbridge, VT: new for this year, a 32 mile route with 4k feet of climbing & 2 times Strava segments on class IV roads for prizes. Food, beer, and live music at the finish. 70% dirt? Segment KOM race

June 18th ECV Hell of the North Shore
Beverely, MA: a long tour of the north shore's secret squirrel 'cross terrain. The start is at the Atomic Café, self supported, limited to 50 riders so register early. One feed stop with fruit, granola bars, & water for your bottles. 50 miles 80% dirt

June 24th, The Kingdom Graveleur
East Burke, VT. This is a long very tough route put together by a very tough pair of cyclists. Mike & Cathy Rowell have a 125 mile loop in the North East Kingdom of Vermont mapped out. It will be hilly, it will be technical in parts. Expect it to be one of the hardest days on the bike you can imagine. It is a test event this year so limited to 20 or so folks that can ride a "Rowell pace" all day long.

June 24th,  RAS Ride
Peru, VT: Described as a Overland Gran Prix lite, 37 miles of stiff climbing on Vermont dirt roads & jeep trails. Provisions from the Hapsgood General Store including a beer/beverage voucher for the first 30 registrants. 37 miles 80%+ dirt benefit ride

June 24-25th Dawn to Dusk Ride
Lexington, MA: Are you up for an adventure? How about a dirt road ride that starts at sunset and continues until sunrise the next day? Overland base is throwing just such a party, including a pre-ride dinner, mid ride bonfire & meal, post ride breakfast, snacks along the way, & support vehicle on route. They are doing it up right. Lights and night riding experience required. 90 miles 60% dirt

June 25th Dirt Road-a-Coaster
Hartland, VT A new race event of 100km with tons of climbing, 6100 feet of elevation gain. Registration on BikeReg.com 80% dirt roads

 June 25th Central Vermont Cycling Tour
Montpelier, VT. Fully supported tour/race around the middle of Vermont. Last year the organizers included chip timing in the long route, so riders who want to "race" the event can throw down. Fully supported stops & sag for the tour. 59 miles 90% dirt.

July 2nd Pemi Baker Adventure Ronde
Plymouth, NH A challenging long route with 3 water stops, 2 meals, and lots of climbing. Farm fresh breaksfast at D-Acres (mile 38) and lunch after the ride at Biedermann's Deli (with craft beer for those over 21). No sag support, KOM contest & prizes for top 3 finishers. 92 miles 60% dirt.

July 7th: Prouty Virtual Dirt Road Challenge
Hartford, VT A very tough benefit ride for the Norris Cotton Cancer Center, 108 miles, 75%+ on dirt roads with 11,300 feet climbing! Self supported but the route crosses 6 Vermont country stores. 10 Strava segments for cumulative time makes up the competition.

July 8th: Raid Lamoille
Stowe, VT: Arlon throws great events, and this is another. 62 miles of central Vermont goodness, which mean 6000+ feet of climbing too. But good food & beer from the Alchemist at the finish. A half distance option also. 62 miles/ 75% dirt

July 9th VO Pave' Madness
Woodstock, VT: Peter Volers & Ansel Dickey have designed a ride to push the very limits of what you can do on gravel bike. If you love the pave' sections of the Overland, this will be all that all the time. Be warned. "only" 23 miles of the most rugged terrain you can ride a rigid bike on. 95% dirt

July 16th Farm to Fork Fondo
Pittsfield, VT

July 16th Plymouth Gravel Grinder
Plymouth, MA: an event benefitting the MS Society and promoted by long time New England race organizers International Cycling. 100 km with 12 sections of dirt road. Chip timed and awards for top 3 in each age category. Tom's wood fired pizza and Independent Fermentation beer after the race. 62 miles 45% dirt

July 22nd JAM Fund Grand Fundo
Southampton MA. Technically with less than 25% of this course on dirt road, this event shouldn't make the list. But this ride is so much fun and supports such good people I have to include it. Jeremy Powers & Alec Donahue host the best cycling party/fund raiser for their development team. Fully supported including an ice cream truck stop, sag wagon, & a pig roast post ride meal. 68/88 miles 25% dirt.

July 21-32rd Nomad Bikepacking Adventure Ride
Lexington, MA: Overland base is all about helping cyclists get out and explore. This new event is designed to help push your boundaries but adding camping to your cycling skills. Over 3 days & 2 nights the ride demonstrate the basics of bike packing. Breakfast and dinner are included each day. Snacks along the route and a roving support vehicle too. Because this is a camping event read the equipment requirements thoroughly at the link above. Total distance is 150 miles approx. 55% dirt

July 23rd Endurance Society Gravel Grinder
Killington, VT a new event from folks who put on other distance races. A mid distance climby route of 40 miles & 4500 ft elevation. 2 feeds & a post ride b-b-que. Timed for results, 40 miles 70% dirt? Race

July 29th IRR 5.0 Irreverent Road Ride
Waterbury VT. Last year Adam St. Germain told me he would do this route on 53x39 gearing & 23c tires. I told him he was nuts, & he was. This year he is warning people to run a minimum 28c tire & 50x34 gearing with a big cassette. This is a long very tough route, after all it runs through the middle of Vermont Gap Land. Fortunately there are many bail out points. Donuts and swag at the start. Self supported 120 miles, 12k climbing,  75% dirt

August 6th NEBRA August Adventure
South Deerfield MA. An event benefiting the New England Bike Racing Association on familiar roads to veterans of the D2R2 & Tour de Heifer. Two routes 75 or 45 miles, both more than dirt than pavement. Post ride meal provided by Hillside Organic Pizza & Harpoon Brewery. 75/45 miles 65% dirt

August 13th Honey 100
Lexington MA. No one throws a bike event like Overland Base Camp. This is a tour of a secret stash of trails suitable for 'cross bikes. Starts and ends with a treats from the Ride Studio Cafe. Fully supported. 62 miles, 65% dirt.
August 19th Deerfield Dirt Road Randonnee D2R2
Deerfield MA, This is the grand daddy of New England dirt events. Almost a 1000 riders will attempt one of 5 routes from 60 miles to 115 miles. The long routes are very challenging with up to 12,000 feet of punchy climbing. The ride has no sag support, but many food stops, a full lunch & post ride meal. This year there is a pre-ride bonfire on Friday night with food & beer from the People's Pint! So many people are riding the routes that finding help with a spare tube is easy to come by. Every New England cyclist should do this ride at least once. Varied, long route=115 miles, 70% dirt

August 26th Honey 101
Sherborn, MA Another great ride by Overland Base. Modeled on the 100 but on a secret stash of trails & dirt roads in Southern Massachusetts. Pre-ride breakfast, 2 sag stops, full support, post ride meal. What more could we want? 65 miles 50% dirt

August 26th Rose Mtn Rumble
Lyndeborough, NH. A ride in south west New Hampshire to benefit the Piscataquog Land Conservancy. 4 different routes, 20 (billed the family ride), 40, 50 & 62 miles. All approximately 70% dirt roads. The 50 mile route last year had 4800 ft. elevation gain, so expect to climb on the longer routes. various 70% dirt

August 27th Farm to Fork Fondo
Freeport, ME

August 27th  The Overland
Woodstock, VT. Peter Volers puts on a dirt road race like no other! He has picked a spectacular finish & a very tough course. 5500 feet of climbing in a 51 mile route. The finish in at the Suicide 6 ski area going down the slope! Food stops with local baked treats for those riding this event as a tour. A post race meal with local beer & kombucha included. Some New Englands fastest cyclocross racers will push the pace at the front, but there is a ton of fun at the back of the field. 51 miles 80% dirt RACE!

September 2nd Detour de Connecticut
Manchester CT. This is a long one, 118 miles long. No support, but plenty of new friends to ride with. The route is a figure 8 so you have a chance to shorten the ride if you like. 118 miles 50% dirt.

September 2nd Rogue Ride
Newport, VT

September 3rd Labor Day 130k
Peru, VT. A new hard ride from RAS Ride. Unsupported but plenty of stores on route. That route is stiff with 7500 feet of climbing over 85 miles. funds benefit Rare Disease Research. 85 miles 50% dirt.

Septermber 7-11th: Five by Five
Boston, MA: A new challenge from Overland Base, a 500 mile 4-5 day semi supported race. Yes, RACE. You'll touch every state in New England while racing back to Boston, details TBA 500 miles 40% dirt

September 9th Kearsarge Klassic Dirt Road Randonnee
Newport NH. The New Hampshire Cycling Club puts on a fine event over a scenic route. 100, 90, or 60 mile routes including a few long stiff climbs. Food stops with water & snacks, mid point lunch, and a post ride meal of home made chilli & baked goods. Starts & ends at a historic barn with a view of Mt. Kearsarge. Various 75% dirt.

September 10th: Cabot Ride the Ridges
Cabot, VT. Cabot VT: Vermont is offering up another hilly dirty charity ride. This one has something for every age, from a 10km family spin to a steep climbing 100km grinder. Aid stations on route, support vehicle, and at the finish wood fired pizza & local ice cream. Family discount on registration for 2 or more, kids under 12 enter Free! Sounds like another good way to spend a Sunday. 100km, 75-80% dirt?

September 10th The Dirty Pizza
Alstead, NH. Orchardhill Breadworks hosts this ride as a benefit for the Putney Ski Club. The ride itself is a 40 mile loop with a bunch of climbing around southwest New Hampshire, as in 4400 ft elevation gain. But the pay off is wood fired oven organic local grain pizza at the end. This is a self supported ride. 40 miles 80%+ dirt

September 16th Ashford Metric Century Gravel Grinder
Ashford, CT. A 65 mile ride to support 3 area charities. Self supported but for good causes. 65 miles 40% dirt

September 16th The Stone Valley 50 Gravel Grinder
Poultney, VT A 50 mile race or 20 mile tour benefiting the Kellen Sam Scholarship. No neutral support so bring tubes & inflator. 2 stocked feed zones. Awards and lunch afterward at Taps Tavern with a pint on the house for racers over age 21. 50 mile Race 75% dirt

September 23rd, NER Fall Classic
Montpelier, VT. The New England Randonneurs Fall Classic has two routes, 114km & 200km. The 114km is approximately half paved & half dirt. The long route is 70% dirt roads. Low cost but brevet type support, which means you, what you carry, and the company you ride with. Good times with good riders
September 24th: Farm to Fork
Berkshires, MA

September 24th, North Woods Gravel Grinder
Rangeley ME, Maine's one dirt road event returns for 2016. Three routes including a new long 78+ mile course. Race results timed in the long route with cash prizes for the top male & female finishers. Rest stops & limited rolling support. Race (in the long route) 35 or 75 miles. 70% dirt

September 24th, Westhill Grinder
Dummerston VT, The good folks at the Putney Westhill shop have been running dirt road rides for decades. Now they are putting on an event. 3 routes, the long one goes over 4 gaps in southern VT. Roughly 45 miles with 4500 feet of climbing so bring your low gears. 19 or 37 miles, 70% dirt

October 1st Fall Foliage Gravel Grinder
Becket MA. A tour through the Berkshires during foliage season. Full support and post ride meal. Starts and ends at a historic bed & breakfast with camping on site. 66 miles 75% dirt

October 1st les 100 B7 
Bromont QuebecNew England cyclocross loves Lyne Bessette (she's married to Tim Johnson after all). Last year she put on a ride around her home roads in southern Quebec. This year it's back using a Strava segment Gran Fondo format. That means the "racing" will be only on the timed segments along the course. Lowest cumulative time for the segments wins. Awards, raffle prizes & post race food at the finish.n 100km (62miles) 95% dirt/gravel road. C'est Bon!

October 1st GUS Adventure Ride
Newmarket, NH

October 7th: Braintree 357 Gravel Grind
Randolph, VT. Short, hard, and very steep but worth the ride. Braintree Gap is one of the hardest climbs in New England. The route covers the 5 roads that cross Braintree Hill. 3 different routes this year, either 18, 35, or 50 miles, all of them very climby. Strava segment KOM contest for the climbs. Post ride burgers & local beer. 35/50 miles 80% dirt, Strava KOM contest.

October 8th: The Kingdom Marathon
Newport, VT. 26.2 miles of dirt road goodness with Pie at the finish. Seriously, Pie, and pizza and Hill Farmstead beer! Plus prizes for top finishers 26.2 miles RACE 90% dirt

October 8th, Apple Grinder Group Ride
Montpellier, VT 35 miles 80% dirt

October 14th: The Formidable Terra Ride
Lexington, MA: Overland Base is adding a dirt road/trail option to their Formidable ride this year. The Terra route is approximate 40% dirt over 110 miles & 8000 feet of climbing. 5 timed sections if you want to get your race on. Breakfast, 2 sag stops, & dinner at the end. Mechanical support provided. Overland organizes some of the best & toughest events in New England.

October 20-23rd: Fall Exploits
Lexington, MA: Another multi day bike packing trip from Overland Base. Details TBA

October 22nd: Vermont Forrest Fondo
Lincoln, VT 42 miles 75% dirt?

November 5th: Mad River Monster Cross
Moretown, VT. Very hilly, self supported, who knows what weather might bring. 50 miles 8700 ft climbing. 2 country stores for refueling. 75% dirt?

November 11th: ESB 100k (Season Ender Bender)
Colchester, VT. Adam St Germain is throwing a last hurrah for the season ride. Packed dirt roads and minimal pave. Self supported with 5 country store stops. 61 miles, 4k feet climbing. 50% dirt?

November 11th, Grafton Cheese Grater
Grafton, VT. A casual ride with 30 & 45 mile options. Mid route stocked sag stop. Benefit for the Grafton Pond trail network.


  1. This is great. Thanks for putting this together.

  2. This list was AWESOME and so appreciated in 2017. Can't wait for the 2018 update!! *hint hint*