1. Mathias Kools
2. Running Trophy Case
3. Running Every Street of Brookline

Running Every Street of Brookline

On April 20th, 2023 I started a project to run every street of Brookline. I finished July 3rd, 2024.

Pre-ramble

At the end of my first marathon I knew I wanted to go again. I wasn’t addicted to running. I was embarrassed. I wanted to go faster. But another 6 to 8 months running the same roads again and again would be grueling. I thought: what if I do the opposite? I could strictly run new roads.

Thinking back to Tom7’s⁰ YouTube video where he runs all the streets of Pittsburgh I had a plan. Searching for existing tools, I found a website called CityStrides. CityStrides is a global leaderboard of runners and how many streets in each city they’ve run. I created an account and started browsing for targets. The Town¹ of Brookline was a lot more workable than the City of Boston. Not only is it where I live. But the town has 10 times fewer roads (100 vs 1000 miles) and five times less total area.

Additionally, I noticed that while the region had two dominant runners, no one had yet hit 100%. Jason Rossman and Michelle Ladonne² hadn’t moved from 95% for weeks. I grew an obnoxious confidence that I would be the first person to ever run all the streets of Brookline.

Here’s how I approached every neighborhood.

(0) Packard’s Corner

I just started running. I started with the streets closest to me: a greedy algorithm choice. With hindsight I’d rather save the quick local segments for busy work days.

One local secret is the clear flour bakery³. Every morning my neighbors line up for fresh bread, a slice of big city life.

(1) North Brookline

This second region, and most of the early days of this project, were completed like a caveman. I’d go to the computer and mark nearby turns and streets I still needed on a piece of paper. I’d leave my house with nothing but sneakers and a GPS to do the route. As a zoomer, I’m used to rotating maps on my phone to align myself. With just paper directions I often ran too far, took the wrong type of turn, and ended up lost.

The gem of this region is Amory park. The boardwalk is a natural treat. If you go at the right time in the year there are wood ducks and turtles.

(2) Corey Hill

Corey Hill rises 200 feet above Coolidge Corner and was my first athletic challenge. That elevation isn’t terrible. But to complete the geography, I needed to run up and down several times. That was difficult to do in 1 run. It’s so difficult, in fact, it’s an exercise of the November project⁴.

This hill was challenging in another way. It pushed how I made directions. What’s the fastest way to navigate these concentric ovals? Is the fastest route the clearest on paper? By the end of the project, I found it was true the other way. Simple directions were the fastest in the field. With precise directions I optimized for extra seconds in planning. But with simple directions I could save minutes from not having to check maps on my phone.

Some of the best secrets in Brookline are the paths. And the premier path is in Corey Hill. It’s the Summit Path. I show this to all my friends and family unfamiliar with Brookline. I’m that proud of it.

(3) Trader Joe’s

This region south of Trader Joe’s is where I first moved in my senior year at Northeastern. I took a chance on “cheap” rent and moved into a town I still called “Brooklyn”. I knew nothing about the place and only drove through it once or twice. In the sixth months of my sublet I fell in love and vowed to live in Brookline as long as I could.

Running through it was a blast from the past. I did have some difficulty with Foster St. getting fenced off for construction. While completing other regions the OSM dataset updated³ and CityStrides gave me the completion credit.

(4) Aspinwall Hill

This second hill of the project was time challenging at first. Round trip I was running 3 miles to get to new running segments, that’s a lot of lost time. To combat this, I enacted strategy one. I would start biking the segments I had already run. I locked up my bike at the base of the hill and would run from there. This allowed me to reach completion rates I had back in the beginning of the project. Once again I was climbing the table and hopeful for a first place finish.

(5) Brookline village

Brookline’s border is huge. And what I’ve found is that instead of one main hub, there are lots of little town centers. Brookline Village is one of them and my favorite. It has a big public library, mixed-use zoning, lots of restaurants, and the best green line.

The roads coil and smush together at odd angles. To tackle these wonky shapes I started using pictures for directions. This worked well with what I call u-shaped roads⁴.

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(6) Fisher Hill

By the time I got here in the project, I had grown in my cartography. By tracing through maps I created a muscle memory I could use on the trail without consulting my papers. I suspect my brain changed in the same way a London cabby’s does when preparing for their test. And that’s a little disheartening. I wasted neuroplasticity points on a skill I’m never going to exercise again⁵.

Fisher hill is a region I’d best describe as McMansion suburbia. Rows and rows of mansions with normal sized yards. I remember running home one day and passing by a William Raveis real estate office. In the window there was the typical printed grid of homes for sale. And it struck me. I’m running amongst millionaires.

This region has two little secrets I’d like to share. You can escape the traffic of Chestnut Hill Ave with the D line footbridge⁶. This became a major throughway for me to bike to West Brookline.

The second secret is Fisher Hill Reservoir Park. Completed in 2016 it is a lovely green carveout in an otherwise well-developed part of town.

(7) High Street

This is the most romantic region of Brookline. The proximity to Olmsted park and the muddy river makes for great promenades. I ran here as a freshman in undergrad. I joined the running club and the group ran us right down the Emerald Necklace at night. I remember running like hell to keep up because otherwise I felt surely lost.

(8) Brookline Reservoir

When I first reached the Brookline reservoir, I knew that I needed yet another change. The bike ride to my starting spot had become so draining that I could only muster up one or two miles of running. I noticed the further I got from home, the less people on foot I saw. I suspected no one would notice my belongings if I left them next to my bike. This meant I could start packing food and water and being more brave about trying to run 5 or 6 miles.

There are two striking spots in this area. The first is the namesake, the Brookline reservoir. This has enough elevation that there is a pretty view of the Boston skyline at night.

The second striking spot of this area was Single Tree hill⁷. The homes here ranged from classy to supervillian mansion. I felt watched as I ran through this neighborhood.

(9) Jamaica Pond

I know the neighborhood watched me as I ran through this opulent area. Private security patrol greeted me as soon as I stepped on these roads. I think they would have harassed me to leave if not for my running LEDs and complexion. Through thick walls of trees I glimpsed what they were guarding. These were the versailles gardens of Boston’s elite⁸. U-shaped driveways with Teslas and other sports cars. And what can only be best described as chateaus and compounds. The lack of light pollution, peace, and quiet was amazing.

The best greenery in this region isn’t Jamaica Pond, but Larz Anderson park. This park is huge and cut into two parts. There was a watery section with a beautiful water fountain in the middle. This was perfect for a picnic. And rising above the water the second half: a wide grassy knoll. This hill comes with yet another view on Boston’s skyline. On the edge is a car museum that looks more like a castle. I haven’t gone yet but vow to before I leave.

(10) West Brookline

A quirky mini-nucleus so separated from Brookline that it should join Chestnut Hill. To get here required a long trek. I went back to the old D-line footbridge trick. I fought through bush overgrowths on the sidewalk of Boylston street. And then dashed across the intersection by the mall.

(11) Walnut Hill

This part of town was quiet and modest. Much of the border here was with nature reserves. The best secret is the western border “service road”. Curious pedestrians can follow the asphalt to a former landfill turned park. I love when towns reclaim land for the living like this. I spent a few minutes running the trails here. It wasn’t worth any points in CityStrides but was worth the joy only fields of grass can bring.

(12) South Brookline

Yet another odd little nucleus of Brookline. The Veterans of Foreign Wars Parkway should be the border. It has a lovely tree meridian down the middle. I suppose enclaved residents wanted to stay after the road came in.

I should say this was hard to bike to. I want to call out the Hammond’s here. Hammond Pond Parkway had no sidewalk at all. And Hammond Street’s sidewalk was broken and dotted with blind driveways.

I used one final strategy to finish this neighborhood. I started walking. A year of looping through Brookline meant my task had become one disconnected avenue at a time. This meant I spent significant minutes in two places: locking up my bike and running back through a completed segment. My adjustment was to only get off the bike, start strava, walk, and when finished get on the bike again.

From what I’ve spied Allandale farms is the hidden treasure here. From what it looks like on the road, it’s a farm selling produce right here in the middle of the Greater Boston Area!

(13) Holyhood Cemetary

I saved these two graveyards of Brookline for last. Holyhood⁸ was the closest so I approached it first. I knew I would have to be careful with these roads. The groundskeepers closed the gates at night. Additionally, I knew I wanted to be respectful as I passed through these parks. I didn’t want to dash by people mourning their loved ones⁹. For Hollyhood I overdid it on being proper. I walked through it the first time around with a polo shirt. And because I didn’t want to disrespect the dead by wearing a hat, I put on lots and lots of sunscreen instead.

(14) Walnut Hills Cemetary

This was a huge cemetery that took two trips to finish. The first time around I ran out of phone battery.

No secrets here but a little story. A woman came up to me asking how she could get to i90: left or right? I guessed right. Looking on maps it looks like she had no hope either way. We were almost exactly parallel to that highway.

Final Thoughts

Photo from Perrin Road.¹⁰

My girlfriend and I took this photo on my last street. I felt overwhelming joy. I was so thankful that I could lead a life like this. It was a dream that I had early on when I started running. And my circumstances allowed me to pursue it. My work life was balanced enough that I had time and energy to get after my goal. My personal life was full of people who were interested in what was important to me and who encouraged me. And my health allowed my feet to take the beating of all those streets.

I loved this goal.

• It challenged me to take something to completion.
• It couldn’t be taken from me.
• It could be paused and resumed around life circumstances without regression.
• It was super accessible by cost. And the on-ramp was low. It was real bare bones planning, logistics and energy required in the beginning. I was walking the streets next to my apartment. How easy is that?
• And finally this goal rewarded creativity whilst also requiring hard work. There wasn’t a trick to invalidate all my previous efforts. But there were little gains to be had here and there.

I recommend running all the streets of your town. If you aren’t a runner, maybe bike every street. This goal created joy in the town I otherwise treated as my mundane. And I think you’d be surprised at what you could find in your own adventure.