Gravel Training Rides

Registration is Live for the Grand Finale Ride May 14!

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Registration is Live for the Grand Finale Ride May 14! 〰️

Join us for a series of gravel training rides! These rides are intended to help you get ready for big gravel rides coming up early in the season. We’re going to be attending Unbound in Kansas early in June, so we’re aiming at that, but many of the people showing up to these rides have other gravel rides on their calendars such as Rasputitsa, D2R2, the Jam Fundo and more. You are welcome to join in regardless of your gravel goals for this year, however, you are required to take the distances, terrain, and self-support seriously.

You are welcome to join for one, some or all of these rides.

These rides are an opportunity to gain fitness and experience riding on dirt. This is also offers you experience packing your gear, food, water, and carrying the load on your body/bike. We have identified stores to stop at along the way to refuel, but are not offering support otherwise.

The last ride of the series is supported given the distance and logistics challenges. There is a fee to cover the costs of making the ride happen and paying someone to support you all day (and it’s a loooong day)!

These rides are full of dirt roads, with nice paved roads as well. Most of the routes are back roads, away from traffic and people. The routes were vetted in the past year or two, so there could be surprises. It is all part of the adventure.

Dates & Locations

  • Done & Dusted - Saturday, April 2:

This ride begins near the Oval in Milford, NH. There is ample street parking. We’re meeting up at Union Coffee Co.

Address: 42 South St, Milford, NH 03055

Details removed, it was a really awesome day, great group, and all ate exceptionally well!

  • Done & Dusted - Saturday, April 16:

This ride begins in Lincoln, MA. This is a holiday weekend so we’re keeping it closer to allow it to hopefully fit into your schedule a bit better. This is a former Honey 100 route of 65 miles, allow 6+ hours to ride it.

Starting time: 8:00am

Starting location: 160 Lincoln Rd, Lincoln, MA 01773 - MBTA Parking lot, where the red marker is here:

Route Notes: This route has not been vetted this year, meaning there could be some trails and parts that were rideable when the route was created that are not rideable now. If a sign prohibits cyclists, or if something doesn’t work, please figure out another way to reconnect up to the route. It adds to the adventure! Every rider is expected to come prepared with the route on a GPS device and battery that will last a minimum of 7 hours.

There are paved roads, trails, dirt roads, paths, etc. Expect anything terrain-wise. Your gravel bike with 32mm or larger bike has adequate tires, all bikes are welcome, just be prepared to take care of your own mechanicals. Skinnier tires are more likely to get flat tires. Mountain bikes will be slower on the roads, but faster on the trails. It’s a trade off. Bring what you want. This is a gravel training ride so bring what you want to get the riding you need and/or want!

We will have one person there at the parking lot to welcome everyone and get everyone rolling. We have one group who will be led at a steady, but not fast, pace. This leader will ride to a “zone 2” pace so if you wish to go faster or slower, you’re more than welcome to do that. The idea is that everyone gets the ride everyone wants and if people end up riding together due to mutually agreeable pacing, great!

Food & Water: Bring sustenance to survive 25+ miles without outside assistance. We have noted ice cream stops at miles 20 & 43. At mile 19, the route turns left - if you/your ride partners want to skip this, don’t do the dog leg and just veer right at that junction.

Water can be refilled in both ice cream stops if you’re not interested in ice cream! If you’re training for a big gravel ride, you’ll need to be able to carry A LOT of water on you and you’ll also want to test out calories, eating a lot and eating a variety of foods/calories in your water to see what your stomach can handle. The route isn’t far from civilization so if you’re running dry, it’s not that far off the route to find a gas station or other shop that has water.

  • Done and Dusted - Saturday, April 23:

This ride begins just south of the New Hampshire border in Winchendon, MA. Two routes are available so you can choose a 100km or 100 mile day. You can also make the decision as to which distance is right for you after starting the ride.

Group starting time: 8:00 am - it’s a long day regardless of distance you’re going. If you want to start earlier or later than this, please just let us know in your RSVP so we know where, generally, you’ll be on the route when.

Details are here: https://www.rideheadquarters.com/gravel-training-ride-3-april-23-2022

  • Done & Dusted: Saturday, April 30:

This ride begins in Barre, MA. It’s a 1 hr drive from Boston. This is a more technical mixed terrain route with 100km option and 100 mile option as well as multiple easy bail out spots. Ideal for Unbound training and equipment testing.

We said that the routes will be posted here by 12pm April 29. Change of plan: we are emailing everyone who has RSVP’d for the ride with a password to access the information by 12pm April 29. Please email us (connect@rideheadquarters.com) if you haven’t received anything in email by April 29 at 12pm.

If you RSVP after 12pm April 29, please allow 3 hours for us to email you the information. We are often in front of customers during the day and email when we are not taking care of people. We email as quickly as possible and appreciate your patience if you’ve waited until the very last minute to RSVP.

Before emailing us: Check your spam inbox to be sure our email hasn’t arrived there. Also, check the calendar. If it’s before April 29 at 12pm, you haven’t missed anything yet.

Starting time: 7:00am - Why so early? Part of Unbound training is the morning routine and backing up the start time is all part of this.

Note: if you RSVP and do not attend without telling us via email that you can’t come, you are compromising the safety and experience of the riders who come out. If you want the route but don’t want to ride with us, please email us and ask.

  • NEXT UP: The Grand Finale Training Ride! Saturday, May 14: 150 miles / all day + Shorter Distance Options

This ride is the most important of all for Unbound readiness! The route we offer is 150 miles in length for a FULL day. It is also an easy route to cut shorter in a number of ways so if you’re not up for a full 150 or aren’t completely sure what you are up for, you’re welcome to give it a shot and cut the route if necessary.

We’re excited to have Red Apple Barn in Phillipston, MA be our home base for this ride! They are offering us parking, restroom facilities for riders before and after the ride, and car camping if you’d like to come out the night before.

Routes that we will provide to you are 67 miles, 100 miles, and 150 miles. We’ll explain how to cut the 150-mile route in case you need to cut it short.

This is a 150-mile figure-8-like route starting/ending in Phillipston, MA, approx 1 hr drive from the Boston area.

If you’d like to join, visit BikeReg now!


There is little to no cell coverage on many parts of the routes.

Assume there will not be a ride leader with you, even if you ride with a group; you’ll be following your GPS computer, therefore owning a GPS computer is a must with at least one back-up power source. 

We will not shuttle riders anywhere or fix your bike on the ride, it’s your responsibility to have a plan in case your bike or legs stop working.


Proper Bike for this Ride

  • 35mm-45mm tires are best suited for the ride. Err on the side of bigger, especially if you’re newer to gravel riding. Feel free to use bigger tires. Your gravel bike is the most appropriate bike for the ride. Mountain bikes and flat-bar bikes are welcome. Narrower than 28mm are strongly discouraged. There is some loose gravel on the roads. Narrower tires are more likely to pinch flat and are less stable than 28mm or bigger. We welcome mountain bikes, fat bikes, and any bike that you feel comfortable completing the distance on in the time frame allotted for the ride.

  • Clipless pedals and shoes. These are important elements of bike control.

  • A bike that’s in safe working order. Make very certain your bike comes clean, lubed, safety checked with fresh brake pads, and tires in good shape. If it's wet on the road or raining, please put a rear fender on your bike to keep you from getting wet. If you’ll be riding with others and it’ll be wet, please be nice to your co-riders and use full-coverage fenders.

Weather: We will ride rain or shine. HOWEVER, if Saturday is looking gross and Sunday is looking pleasant, we are likely to move the ride to the next day for sanity purposes. Dangerous weather is definitely a no-go.

Last Minute Information: This page will be updated with the latest information. We will only email riders if some exceptional thing has happened after 12pm the day before the ride. We will post Tweets when this page is updated so you know to look here!

Unregistered riders or riders who haven’t signed the waiver may not participate.

Waiver: Ride Headquarters requires a signed waiver before your first ride. Please fill it out online prior to your first ride.

Contact Information: Email connect@rideheadquarters.com with questions.

We are reacahable at the ride at 413-461-7433. If you need to reach us IMMEDIATELY, please do not txt, but ring twice if we can’t get to the phone for your first call.

Riding Rules, What to Bring, How Our Rides are Different: All riders are required to read and are expected to abide by These Rules. Note: ALL rules stated here on this page override any conflicting rules you see on our typical ride rules.