Boston’s Best Running Routes

When it comes to running cities, Boston is one of the best you’ll find in the United States.  Most people know it for the Boston Marathon, which attracts thousands of celebrated marathoners from around the world every April, but what makes the city a regular runner’s dream is the fact that it has so many varied and lengthy running routes for everyone to enjoy, from the weekend warriors to the elite-level athletes. Over the past 18 months, I have tried to explore as many of these routes as the weather and my body’s limitations would allow. Having gained all that experience, I want to share my five favorites for any BC Law student—or anyone else who stumbles upon this post—to use as a guide for their own running adventures.

Over the years, this blog has had its fair share of posts about the positive aspects of running. However, there are dangers to this practice, as evidenced by one of my fellow bloggers, who recently wrote about ending up on crutches after an ill-fated run under the stars. With that harrowing tale in mind, I should say that, while I endorse running whenever the spirit moves you, readers should know that if you run one of these routes at night, you do so at your own risk. With that disclaimer now firmly established, here are my five favorite Boston-area running locations.

The Top Five

1. The Emerald Necklace

The Emerald Necklace is a unique and special urban running experience. The Necklace is an interconnected system of parks stretching over seven miles from end to end. It “begins” (depending on your perspective) near Fenway at the edge of the Charles River. You can then run through continuous green spaces all the way to the Arnold Arboretum in Jamaica Plain. Along the way, you will run beside stretches of river, woods, and numerous ponds. Small side trails also weave in and out of the paved sections of the Necklace, which can provide a nice change of terrain if you’re into that kind of thing. My favorite way to experience the Necklace is to start at the Fenway end and run to Jamaica Pond, ideally reaching it right at sunset to catch some tangerine and purple skies reflecting off the water’s surface. Conversely, you could start at the Arboretum or the Pond and finish up at Fenway. That route allows the runner to enjoy a beer or some food at the Time Out Market to reward their athletic endeavors. You can’t go wrong either way, or any way you choose to experience the Necklace.

Emerald Necklace Map: https://www.emeraldnecklace.org/wp-content/uploads/2015/11/Emerald-Necklace-Map.pdf    

2. The Fells

The Middlesex Fells Reservation, colloquially known as the ‘Fells’,  is a public recreation area with over 100 miles of mixed-use trails for hiking and running located just off I-93 in between Malden and Stoneham. Those locational markers may mean nothing to you, but if you are into trail running more than street running, then the Fells is the place for you. Despite the hum of traffic nearby, you will be completely submerged in trees and treated to lovely views of the Middlesex Reservoir and the Boston skyline as you traverse up and down the rocky hills that make up the terrain of the park. 

One great route for those who like to push themselves physically is the Skyline Traverse, an eight-plus-mile route that traces the park’s outer perimeter. It involves a fair amount of climbing, and I’d advise (from harrowing personal experience) that you bring water with you if you plan to tackle it in the warmer months. Other notes of warning: this place gets very busy on weekends when the weather is nice, so try to plan your excursion for weekdays or get used to getting up before the sun to beat those crowds.

Downloadable Map: https://www.mass.gov/doc/middlesex-fells-reservation-trail-map/download

Park Information: https://www.mass.gov/locations/middlesex-fells-reservation 

3. The Charles River Esplanade Et. Al.

This one is an easy one to get to from any part of the city and a staple for anyone bold enough to train for a marathon. I am highlighting the Esplanade, which runs along Storrow Drive near Back Bay, because that is the 3-mile section I hit the most often. My typical Charles River route begins with crossing the Boston University bridge. I then head east along Memorial Drive toward the North End, before crossing back over the river at Longfellow Bridge and running back up along the Esplanade in Back Bay toward Brookline. But do not let my desire for routine limit your running imagination. You’ve got the Paul Dudley White Bike Path and the Charles River Reservation area, to name just a few other ideal spots, where you can stretch those legs and build up to marathoning distance. The best part of the Charles River is that there is no shortage of entry points and no real limit to how far you can go, if your legs can take you there. 

I will warn any wary or crowd-averse runner that many people love to use these paths, so expect some crowds, some speeding bikes and mopeds, and definitely expect some people to unexpectedly stop for their Instagram moments right in front of you. If you like crowds and obstacles when you run, though, you can also veer off the Esplanade and take your run through Back Bay, by the State Capitol Building, and down through Boston Common, which has the fun side benefit of squeezing a lot of sightseeing into a small timeframe. When the weather permits, Night Shift Brewing has a beer garden right alongside the path, which can make for a great post-run hangout spot or place to meet up with friends.

Charles River Esplanade: https://esplanade.org/wp-content/uploads/2016/06/Esplanade-Map.pdf 

Charles River Reservation Maps: https://www.mass.gov/locations/charles-river-reservation 

4. Chestnut Hill Reservoir 

Tipping my cap here to the BC undergrads by picking their number one running spot. A loop around the pond is about 1.5 miles, so if you’re into that kind of thing, you can just run nice circles with views of skyscrapers in one direction and the spires of The Heights in the other to your heart’s content. I tend to run to the Reservoir from my apartment in Coolidge Corner, do one lap around the water before heading back along the C line of the T. This makes for a nice 6+ mile journey with a nice mix of dirt paths and sidewalks. I also enjoy that it gives me a mix of urban running through more busy areas and a place to push the pace a bit more when I get to the Reservoir itself. The true sickos can really push themselves by running up the famous Million Dollar Stairs on BC’s main campus as a finisher after putting in some miles on the path. It involves a fair bit of suffering when the legs already feel tired, but the views at the top of the stairs make the pain worth it.

Chestnut Hill Reservoir Map: https://www.mass.gov/locations/chestnut-hill-reservation 

5. Margot Connell Recreation Center Jogging Track

Okay, readers will call me crazy for this one (if you’ve gotten this far though I would say you’re the crazy one so there), but when the temperatures plummet into the single digits, as they seemingly have for the past three months, you too may find yourself growing fond of the bouncy red loop on the fourth floor of the Rec Center. It takes 4.75 revolutions around this bad boy to achieve one mile of linear distance. That means if you want to stack the miles, ready yourself to become very familiar with the scenery: an overlook of the basketball courts (you might get to see volleyball games or fencing practice), the stretch between the bathrooms and the cardio equipment (treacherous), the small hill (unclear why it exists) that makes up the back straight over the indoor tennis courts, and the final stretch where the course zig-zags around the elevator bay (electrifying). I never thought I would learn to love this rat’s maze of a course. Yet somehow over the course of a diabolically frigid winter, I have come to appreciate all that it has to offer.

Track Map (in case you get lost): https://www.bc.edu/bc-web/offices/rec/about/facilities/margot-connell-recreation-center.html 

Honorable Mentions

Heartbreak Hill

Confession street: I’ve never run this particularly famous stretch of asphalt, but I can imagine it’s a great experience for those who have a real affinity for the Boston Marathon. Added benefit is that it’s so close to campus that you can run it without having to suffer for 20+ miles beforehand.

Blue Hills Reservation

Blue Hills is a lovely place and only relegated to honorable mention because it’s quite like the Fells, and I just so happen to prefer the Fells. But if you happen to live south or east of Boston, then this is probably the preferred place to get your trail running fix. 

Blue Hills Reservation Map: https://www.mass.gov/locations/blue-hills-reservation 

Hammond Pond Reservation

Hammond Pond is a nice, small alcove of woods and rocky climbs just outside of Newton. The reservation is not too expansive, but it does provide a nice taste of wilderness if you are crunched for time or not in the mood to negotiate Boston area traffic. The other benefit is that it’s basically right next to a massive shopping center, so you can tie it into an errand or grocery run if you want to make the trek doubly productive.Hammond Pond Map: https://www.mass.gov/locations/hammond-pond-reservation


Ian Hurley is a second-year student at BC Law. Contact him at hurleyia@bc.edu.

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