Hallowed Groad

Hallowed GroadHallowed GroadHallowed Groad

Hallowed Groad

Hallowed GroadHallowed GroadHallowed Groad

An autumn CELEBRATION OF NEW ENGLAND'S HISTORY & open SPACE

An autumn CELEBRATION OF NEW ENGLAND'S HISTORY & open SPACEAn autumn CELEBRATION OF NEW ENGLAND'S HISTORY & open SPACEAn autumn CELEBRATION OF NEW ENGLAND'S HISTORY & open SPACE

Self-supported scavenger hunt adventure mixed-terrain adventure ride through the backroads & trails of Metrowest Mass.

An autumn CELEBRATION OF NEW ENGLAND'S HISTORY & open SPACE

An autumn CELEBRATION OF NEW ENGLAND'S HISTORY & open SPACEAn autumn CELEBRATION OF NEW ENGLAND'S HISTORY & open SPACEAn autumn CELEBRATION OF NEW ENGLAND'S HISTORY & open SPACE

Self-supported scavenger hunt adventure mixed-terrain adventure ride through the backroads & trails of Metrowest Mass.

Hallowed Groad on InstagramHallowed Groad on StravaJillian on Strava

BE AWARE, BE CAREFUL, BE KIND

This is a self-guided, self-supported ride. Be cautious and use good rider judgment. The crypt keeper is waiting for you to make bad decisions. 


 Watch for signs and heed all warnings – No mystic portal or route will be out of reach of cyclist or others, so stay true and don't trespass.


You will find others traveling along the Hallowed Groad on bike, by foot or four footed beasties without understanding or inclination of the mystic path they tread. Pass politely and give warning as appropriate.


While we may never hear if you and your team were mean of spirit during your ride, we believe in the rules of karma - which is it always comes back.

Prepare for adventure

YOUR STEED

Gravel, cyclocross, and mountain bikes will all work and each will have their advantages and disadvantages along the way.  The trails are fully rideable on a gravel bike with the exception of necessary dismounting for fallen trees and high bridges.


In this case, size does matter – The larger the tire the better with a recommended minimum of 40mm. 


If you show up squeezing 32mm tires in your road bike, your team will eventually leave you for dead.

YOUR ARMOR

While a medievel helm may feel theme appropriate, we suggest a bicycle helmet. Charms or other wards are encouraged.

POTIONS AND ELIXIRS

The Groad is long – do not underestimate the time it will take!

While there may be places to seek sustenance, nothing in this life is guaranteed, so be sure to bring food and drink needed to sustain yourself and prevent you from fading into the darkness.

TOOLS OF THE TRADE

You and your team travel the Hallowed Groad without the support of mechanics or other tradesfolk. Follow the teachings of the Scouts of Girls and pack the tools you need to avert potential distaster.

ITEMS OF NAVIGATION

You will need a GPS device to follow the course.

Whether you are guided by the stars or by the gods and goddesses of Ride with GPS, be sure to bring the navigational devices needed to ensure your safe return home.


There are no course markings, although portions of the course are marked by the Bay Circuit Trail badges and other local trail blazes. It can work well to designate a primary navigator on your team, with others also following the GPS route as backup. 

"Adventure is worthwhile in itself."

BEFORE YOU RIDE

BEFORE YOU RIDE

BEFORE YOU RIDE

  • Gather your crew
  • Register your team using the form below
  • Join the Strava Club
  • Connect with "Jillian" on Strava
  • Review the route and waypoints (when made available)
  • Select your bike and await the route and mystic portals

AS YOU RIDE

BEFORE YOU RIDE

BEFORE YOU RIDE

Choose one member of your team to do the following:

  • "Announce" your team's departure on the Strava Club - share your team name and a team photo
  • Track your ride
  • Find each mystical portal (there are 7 in total) and document
  • Complete your ride
  • Add Jillian to your ride – THIS IS THE MOST IMPORTANT
  • Name your ride 2025 Hallowed Groad - TEAM NAME
  • Save to Strava with photographic evidence

FINISH YOUR RIDE & PREPARE TO BE JUDGED

Rides must be completed and documented by 11:59pm on Sunday, November 9, 2025 to be considered for prizes. Winners will be selected and announced no later than November 13, 2025.

From those who live to tell the tale

prizes will be awarded

For each Mystic Portal  passed and documented, your team will receive one entry for our prize – a gift card to Fireside Tavern Sherborn, a establishment of good repute for food and drink.


An additional gift card will be awarded to the team that best exemplifies the spirit of the Groad (or have really awesome costumes)

THE MYSTIC PORTALS

Mile 1.1 Take a Seat

Mile 5.3 A Cemetery in Braggville

Mile 5.3 A Cemetery in Braggville

On the shores of Lake Winthrop you are invited to take a seat and enjoy the view – but don’t linger for long for your journey has just started.

Mile 5.3 A Cemetery in Braggville

Mile 5.3 A Cemetery in Braggville

Mile 5.3 A Cemetery in Braggville

"We think you can" find inspiration from the children's classic starring a determined train as authored by a descendent of the Bragg family buried here.

Mile 7.8 Along Holliston Highway

Mile 5.3 A Cemetery in Braggville

Mile 7.8 Along Holliston Highway

A wooded highway paved with good intentions (but little else) leads to this portal which may leave you feeling out of balance.

Mile 11.7 Ready to Run

Mile 14.1 At Trails End

Mile 7.8 Along Holliston Highway

Generations of those fleet of foot (and some would say, less than sound of mind) have started their own journey here.

Mile 14.1 At Trails End

Mile 14.1 At Trails End

Mile 14.1 At Trails End

The trail certainly ended here for this possibly polygamist family, but yours is not quite done. 

Mile 18.1 In the Ruins

Mile 14.1 At Trails End

Mile 14.1 At Trails End

Recently threatened by modern forces, these ruins remain intact thanks to neighborly interventions and one skeletal guardian.

BONUS: Mile 21.1 Mother & Child

BONUS: Mile 21.1 Mother & Child

BONUS: Mile 21.1 Mother & Child

Should you choose to continue your travels, a bonus awaits. Follow the trail of gold and orange leaves to where a mother and child look down (because she's tall, not because she's judging) upon our travelers. 

The Route

GROAD NOTES

COURSE DETAILS

The more you pay attention to this section and preview the course map, the smoother your ride will go. 


  • MILE 0.8: Enter the woods at the end of the park road. You will immediately encounter a narrow trail with plank bridges that need to be walked. 
  • MILE 1.3: Exit the cemetery over the stone wall onto the trail. Follow the trail along the lake behind the houses (one more plank to cross), which will lead to a sidewalk path up to the street. 
  • MILE 6.4: Enter the dirt Adams Street lot. Here you will run the gauntlet of mountain bikers as they groan and point at the funny drop handlebars that have clearly lost their way. Continue into the singletrack at the back corner of the lot. You have entered the most technical section of the course. It’s fully rideable by some, with quick hike sections for some others. As you finally exit the woods you’ll pass College Rock - a popular rock climbing training area. 
  • MILE 15.6: You will pass the entrance to Hopkinton Conservation North Mill Trail Head on your left. The GPS course keeps you on the road, but if you’re feeling adventurous and want to break up this road section, this trail “shortcuts” the road. Your GPS should have these trails on the map. (Hint: we think the wider loop accessed from the middle connector is better than the inner loop).
  • MILE 20: Hey there’s my car. So this is the end….or is it?
  • If you keep following the GPS course there is a quick 1.7 mile loop to another bonus waypoint. It’s fully off-road. 

OTHER DETAILS

PARKING 

If you are driving to the start in Holliston, public parking for the rail trail is available around Blair Square. You can use 1 Front Street for GPS guidance.


FOOD

  • COFFEE HAVEN
    Coffee Haven is right at the start along the rail trail. They have beverages, pastries, and great lunch sandwiches.
  • BOSTON HONEY
    Boston Honey has a retail store at the intersection where the course enters the Holliston Rail Trail. They sell beverages and ice cream. Typically open weekends. 
  • MUFFIN HOUSE
    Muffin House is a little off the course in downtown Hopkinton. If you travel down the sidewalk from the Hopkinton Green you’ll find the Muffin House in a small white building. Other options are also across the street. 

HOW TO JOIN

Anyone may ride the Hallowed Groad, but to be in contention for our prize, you must register and follow the rules of engagement (above)

  1. Find some friends, line them up in a row, and now pick your favorites dodgeball style. Teams of 3 –6 are ideal. The rejects can form another team hellbent to defeat you.
  2. Now think of a team name – no extra points for creativity.
  3. Use the form below to tell us about your team.
  4. Join the Hallowed Groad Group on Strava.
  5. Follow Hallowed Groad on Instagram for updates! 
  6. Follow the rules above.

Copyright © 2025 Hallowed Groad - All Rights Reserved.

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