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Very Special Ride: Highpoint Three-Day Ride

Some of the participants from last year stand atop Mt Greylock.

Some of the participants from last year stand atop Mt Greylock.

The Highpoint Ride does just that – brings us to the highest point in Massachusetts, and back down again – with a day of rest or western Massachusetts riding in between. This ride is so beautiful that we’re offering various distance options and we’re staying an extra day – so no one is left out and we have time to enjoy western Massachusetts on Saturday. All Highpoint cyclists are riding to the top of Mt. Greylock on Friday before sunset – regardless of which distance you choose.

UPDATES: All Highpoint riders can look forward to a 20-minute free massage upon arriving at Mt Greylock by Kimber Green. She is offering half-hour and hour-long massages on Saturday for riders, too. She’s offering dramatically discounted rates for the Saturday massages. $40 for an hour of bliss the day after this ride is awesome. Kimber is local to us here and is a top massage therapist.

The Highpoint Packing List is available now, too: How to Pack for Highpoint

Register Now HenryHighpoint

When Is This Event?

August 15th-17th, Friday through Sunday. For those doing the full 300+ miles, first rollout is at 6am Friday morning (earlier starting times will be available).  We’re all arriving at Greylock before sunset.  We’ll all be back home by sunset on Sunday evening. A complete schedule for start times at the remote starting locations will be published well in advance of the ride. Saturday will be spent riding or relaxing in western Massachusetts – your choice! We all roll out together on Sunday morning at 7am to return to the Studio or your remote parking location, depending upon where you started your ride on Friday.

Why Do This?

P1030777 Massachusetts is a beautiful place to ride, and the Highpoint route explores some of that beauty we don’t typically see; and it all culminates at the top of Mount Greylock – the highest point in Massachusetts.  At the top we’ll watch the sunset before we have a special private dinner at the Greylock’s Bascom Lodge.  And then we’ll sleep really well.  On Saturday, we’ll enjoy a nice breakfast and have various riding and non-riding options for the day. On Sunday morning we watch the sunrise from Greylock and then ride back to the Ride Studio Cafe (or your remote starting location). The Highpoint ride gives you a rare opportunity to push yourself – to ride further, to ride challenging terrain – all while having a very good safety net of a fully-supported tour.  We have one vehicle for every 15 riders so you’ll never be too far from support.


The Studio is providing all the food you could possibly want. We’ll have all of the sweet, salty, and savory treats you will want to fuel long, fun days of riding. Think Sul Posto x 4!   We’ve planned many rest stops where we’ll be providing food and drinks.  Expect breakfast, lunch, and dinner on Friday and Sunday, along with endless snacks. We will have food planned for all dietary restrictions.  Food will be on your own on Saturday considering everyone will likely choose a different plan for eating, riding, and recreating.BOHLYSaCMAA7mU-.jpg_large


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  • Bascom Lodge at the top of Greylock.  This is a beautiful rustic lodge with limited space.  The Studio has reserved the entire lodge for both Friday and Saturday nights so we’ll have it all to ourselves. Bunk beds and a few private rooms with a few queen-sized beds are provided at Bascom. Sheets, towels, and pillows are provided. You may also sleep in your sleeping bag on the lodge’s covered porch. We will give you a $100 RSC gift card if you choose to sleep on the porch instead of in a bed.
  • Bascom will provide dinner to everyone Friday evening when we arrive (buffet style that we arrange with them) and breakfast buffet-style Sunday morning.  Check out their menu. If you want to eat there Saturday for breakfast, lunch or dinner, their restaurant will be open. Food Saturday is on your own.

Accommodation preferences are based on sign up order; first to register (and pay) get first choice of lodging. We have room for 36 people to sleep in beds.


Remote Starting Locations

More information about exact parking areas for the remote starts along the route will be available well before the ride. If you are starting at a remote location, we will tell you where to park your car and when your ride will begin. (Only the riders starting at RSC have a very early start.) Luggage for all riders will be driven to Bascom Lodge so your things will be waiting for you when you arrive at the lodge. The details surrounding the remote starts and luggage handling will be announced once the route is finalized. The ride distance options are the following:

  • Option 1:  The Thermopylae Triple Century.  This ride departs from the Ride Studio Cafe on Friday morning – after a few kick starter espressos – and rolls beautifully through some of the most memorable roads you’ll ever see.
    • Start Time: 6am.  One-Way Distance: 163 miles. Starting Location: Ride Studio Cafe.
  • Option 2:  The Double Over Century.  Two hundred miles is quite an achievement; a distance about which most of us only dream.  With a good night’s rest at the midpoint, maybe now is the time to add this two-day-double-century to your list of ride accomplishments.
    • Start Time: 8:15am One-Way Distance: 100 miles. Starting Location: Westminster.
  • Option 3:  The Two-Times a Metric Century:  This challenging and unique two hundred kilometer route promises Greylock’s gift of exceptional multiple views.  And the company of tongue dragging cyclists.
    • Start Time: 11am One-Way Distance: 62 Miles. Starting Location: Erving State Park.
  • Option 4:  The Climbingest Century.  With 100-miles of amazing roads, this ride lovingly provides you the most climbing per mile of the four ride options.  This may well be the most rewarding century you’ll ever ride.  And you’ll get the prize of a sunset on Greylock.
    • Start Time: 12:30pm One-Way Distance: 50 Miles. Starting Location: Greenfield.


It is very important to be realistic in your riding abilities when choosing which distance to ride. This is a difficult route that is constantly going up or down and it will feel like there is a lot more up than down, especially on Friday. Riders are required to maintain at least a 12 mph average in order to finish in time for sunset. The 12 mph includes stopping time. If a rider falls behind the last support vehicle (which will be driving to maintain this 12 mph average), the rider will be expected to sag the rest of that day. There will be plenty of opportunities to stop for food, bathrooms and to snap photos if you choose. The time, however, can add up quickly making for rushed stops. In considering your pace, don’t forget the chance of mechanicals and how much slower it is to ride uphill than on terrain we usually find in the greater Boston area.  You won’t want to stop for too long.  Stopping often for short periods is better than a few long breaks.

Why Mount Greylock?

Here are a few fun facts about The Greylock:Greylock

  • Greylock is the highest point in Massachusetts at 3,489 feet, or 1,063 meters.
  • The Highpoint climb provides about 2,700 feet of continuous climbing from the river valley to the mountain’s peak.
  • Greylock is the only “Hors Categorie” climb in Massachusetts – by Strava’s standards.  This means that the climb is “beyond categorization” because it’s so difficult!
  • Greylock offers the longest climb in Massachusetts at 9.4 miles with an average grade of 5.9 percent.
  • Greylock provides a maximum grade of more than 22 percent.
  • Greylock is known for its memorable views of five states.

Requirements for All Participants

  • Your Bike is Safe:  Your road bike passes the Ride Studio Cafe’s safety check – and is tuned up by RSC.  This is a free service to all Highpoint registrants.
  • You wear a helmet: You must wear your helmet at all times you are on your bike.
  • Use a Garmin Computer:  You own a Garmin 200 or higher.
  • Know How to Use a Garmin:  If you’re new to Garmin the Studio is providing a training class.  This class is free to all Highpoint registrants.
  • Know How to Read a Cue Sheet:  The Studio has a document for this.
  • Know What Safe Riding Entails:  Participation in at least one of RSC’s Highpoint training rides.  These rides are free.
  • Agree to Ride Safely:  Sign the Ride Studio Cafe Liability Waiver if you haven’t already done so.
  • Complete the Highpoint pre-ride questionnaire (included in the online registration form).
  • Be Prepared:  Bring to the ride all the equipment specified in the Equipment section.
  • Capable of Completing the Ride:  You have completed a 100-mile ride this season.  You must have a GPS or RUSA record of the ride.  If you haven’t ridden a century yet there are many offered by us and other organizations before mid-August. We’ll update you on these options when the century rides begin.
  • Capable of averaging 12-Miles per Hour for 13-Hours:  This includes rest stops.  If can’t do this you will be in the van because we don’t want any cyclists riding unsupported or in the dark in the Greylock area.  If the last van passes you at any point, the van will pick you up.  This van will be maintaining a 12-mile per hour average speed.



$475 per participant. This price includes:

  • Comprehensive Rider Support: all day Friday from 4am until you arrive at Greylock and all day Sunday until you arrive at your destination.  We have multiple vehicles along the route; you’ll never be farther than thirty-minutes away from a van or car, good food, and technical support.  We also have backup bikes, wheels, and all things bike related so we can assure that your bike won’t stop you from riding.
  • Lodging:  Friday and Saturday evening lodging either at Greylock’s Bascom Lodge.  Lodging space is determined by those that sign up first; they get lodging preference.
  • All Food and Drink on Friday and Sunday, including:
    • Private dinner on Friday evening at Bascom Lodge
    • All food along the route on Friday and Sunday, including breakfast, lunch, and any snack you could possibly want
  • Please note that since everyone will have a different plan for Saturday, snacks for riding are included, but breakfast, lunch, and dinner are on your own.
  • Bike Tune-Up and Safety Check certification by Ride Studio Cafe.
  • Garmin Training:  A computer training class designed specifically for the Highpoint ride. (Date tba.)


  • Highpoint T-Shirt available for participants to buy ($25):  A limited edition US made organic t-shirt with a very special design.
  • Ride Saturday: We’ll lead a couple of ride options on Saturday from the top of Mt Greylock, around the area, and back again, if you want to ride.
  • Include your family or friends: Last year we had riders’ families and friends meet up with them at the lodge for dinner the first night and it doubled the fun for all! Now that we have Saturday, we encourage you to invite your family to come up and spend the day together doing something you’d all enjoy.
  • Massage on Saturday: We’re arranging for a massage therapist to come to Bascom on Saturday. What better time to be pampered?

Sunday evening after everyone returned, all were still on a high from Highpoint – and wearing their t-shirts.


The Equipment List is extensive & a printable version will be posted here. The good news is that most of everything you bring will ride in one of our support vehicles. The list contains suggested and required items so you have a good ride. Feel free to bring other personal necessities that we haven’t included. What’s most important for you to know at this time is that we are requiring use of a Garmin GPS so everyone stays on course (this is critical for full support and there isn’t a lot of extra time in the day to spend navigating). Other special equipment that is on the list that you may not have is the proper gearing on your bike. Our Endurance Team who regularly completes very long rides and races on difficult terrain such as this route all ride a small 34-tooth front chainring and biggest cog in the rear cassette has 32 teeth. Gearing much higher than this will make the ride much less pleasant. We can’t emphasize enough how challenging this route is and anyone who attempts the 163-mile ride really needs to be ready for the difficulty. We did the ride last year, so if you have questions, we can tell you what to expect. Where it comes to tires, nothing skinner than a 23 should be on the road and we advise wider than that for fewer flats and a more comfortable ride.


Contact the Ride Studio Cafe by email: highpoint@ridestudiocafe.com or Phone: 339-970-0187 After reading all of this through, hopefully you are as excited as we are about going on this adventure. We look forward to enjoying this weekend in the middle of August with you. Register Now

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