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Top 12 Running Hills of (Greater) Boston


The Best Running Hills in the Best Running City – Boston

Boston is running city. We complain about the nor’easter that hits every April, we yell is disbelief if the Pats don’t have a perfect season and we crowd the streets with fans for 26.2 straight miles of Boston Marathon glory. At indoor track meets, national and world records are broken every year by stars of the sport like Galen Rupp, Edward Cheserek and Shalane Flanagan. A deep running culture is cultivated by prominent clubs like The Heartbreakers, Trail Animals Running Club, the BAA and November Project. As a non-grid city, there is seemingly endless access to safe and varied running routes. Hit Charles River or Commonwealth Ave where you’ll likely spot a sub 2:20 marathoner. Did I mention we have a marathon? Additionally, Boston has great running hills, which is the focus of this article.

A photo of the Boston Marathon at Mile 20 in front of Heartbreak Hill Running Company
Mile 20 of the Boston Marathon before Heartbreak Hill. Photo: Josh Campbell

Boston is a runner’s dream. Why then, do I sometimes hate it?

I am a mountain runner living in a city. I’m training for races with 10,000ft+ of vertical gain, but nothing can replace the fresh mountain air whiling ripping through single track trails. Running up and down makes me feel alive. Luckily, I am easily entertained. Hill repeats are my jam. Incorporating elevation makes me faster when I’m running an ultramarathon or any distance

Luckily, these benefits aren’t only for crazy people like me. Running hills – particularly in speed workouts – significantly improves running economy and lactate threshold. These two endurance traits are important indicators of fitness for 5k and marathon runners alike. Getting in a hill workout here isn’t hard – if you know where to look. And for all you crazies, putting in 5,000ft or even 10,000 feet of elevation gain isn’t unrealistic weekly goal, either.

Listed below are the insiders scoop on the best running hills in Boston. Each neighborhood is only allowed one hill, sometimes accompanied by an honorable mention. There is no particular order other than you will find the most classic hills, i.e. my personal favorites, towards the top. Proceed with caution. Hills are not for the faint of heart. Whether you are visiting Boston on a trip or looking to take your running to the next level, here you can find your vert. Did your hill make the list?

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Listed in order: Summit Ave (Brookline), Heartbreak Hill (Newton), Beacon Hill (Back Bay), The Great Blue Hill (Milton / The Blue Hills), Bussey Hill (Jamaica Plains), Eastern Ave (Arlington), Bear Cage (Roxbury), Spring Hill (Somerville), Wright’s Tower (Medford / The Fells), Savin Hill (Dorchester), Prospect Hill Park Auto Road (Waltham), Bunker Hill St (Charlestown) and Hospital Hill (Quincy).

Heartbreak Hill (Newton) – Strava Segment

Distance: 0.34 miles Elevation Gain: 83 feet Grade: 4.5%

Heartbreak Hill, a true classic. The best running hill in Boston? Definitely not. Nonetheless, this is a popularity contest and Heartbreak wins.

Located at mile 20 of the Boston Marathon, I prefer to run Heartbreak starting at Grant Ave to avoid a busy intersection. With carriage road access, you don’t have to worry about traffic. The hill is pretty easy, just run up it! The entire Heartbreak Hill actually has 95 feet of elevation gain.

Honorable Mention: Washington Street to Heartbreak encompasses of the Newton Hills of the Boston Marathon, a 3.3 mile stretch featuring 243 feet of elevation gain. An alternative hill, Newtonville Ave from Cabot Park to Summit St is nastier with a 7.8% grade.

Summit Ave (Brookline) – Strava segment

Distance: 0.37 miles Elevation Gain: 180 feet Grade: 9.2%

Some hills have magic. Summit Ave is one of them. Start at the base of the hill at Beacon Street. The hill has a subtle increase in steepness half way through. The hill flattens at the top, but continue all the way to the park. That wasn’t so hard, was it? The November Project runs a morning Friday workout, if you’re looking to meet a few friends.

Honorable Mention: My friends would kill me if I didn’t include Fisher Hill and Aspinwall Hill to the list. Brookline has the best hill running in Boston outside of trail reservations like the Blue Hills and the Fells.

A picture near the summit of Summit Ave for the article Top 12 Running Hills in Boston
You’re so close to the top of Summit Ave, but also so far!

Beacon Hill (Back Bay) – Strava Segment

Distance: 0.12 miles Elevation Gain: 52 feet Grade: 8.2%

Beacon Hill has at least nine ways to run it, but I picked Joy Street because of the name. The area is very pedestrian friendly, but watch out for traffic. Enjoy cobble stone sidewalks! You can extend this route to Mt. Vernon Street for another 25 feet of elevation gain. As I said, Joy Street is not your only option. Any of the surrounding streets will also bring you Joy.

Fun fact: Boston originally had three prominent hills. Beacon Hill still remains after the big dig. What is the best way to run up Beacon Hill? That is a tough question – comment below if you have strong opinions and I’m open to reconsidering.

Honorable Mention: Beacon hill has plenty of opportunities for vert. One of my favorite Boston city workouts is to run every road north of Beacon Hill, from Grove to Temple.

The Great Blue Hill (Milton / The Blue Hills) – Strava Segment

Distance: 0.40 miles Elevation Gain: 364 feet Grade: 16.7%

Are you a masochist? Great, this one if for you.

There is a parking lot at the base of the ski hill. Park there. See the ski slope. Run Up. Don’t stop until you pass go. Collect $0. At the top, you have the option to join Summit Road for another 80ft of elevation gain to make it to the buildings at the top of the Great Blue Hill. Many runners will use Summit Road instead of the ski hill instead.

Honorable Mention: Literally anywhere in the Blue Hills. Particularly the Skyline Trail.

A picture at the base of the Great Blue Hill, which is a very long and hard hill to run
Cmon, it doesn’t look that bad, right?

Bussey Hill (Jamaica Plains) – Strava Segment

Distance: 0.57 miles Elevation Gain: 117 feet Grade: 3.7%

The Arboretum is such a lovely place, at least for those seeking vert. This route looks like a lollipop or a poop emoji, your choice. If you enter through the visitor center, continue on the main road. After about a half mile, the road u-turns and rises. This is the start. Continue up and slowly loop left until the road ends. You’ll have a nice view of the Arb and some of the city.

Honorable Mention: Peter’s Hill features nice gain. Starting at Bussey Street, you follow Peter’s Hill Road to the right and follow a footpath to the top for great city skyline views. 131 feet of elevation.

Eastern Ave (Arlington) – Strava Segment

Distance: 0.86 miles Elevation Gain: 303 feet Grade: 6.7%

Start at Hillsdale Rd and Spring St. Be aware of traffic. Spring Street will eventually turn into Eastern Ave and if you keep going you make it all the way to the water tower. If water can make it uphill, why can’t you? Alternatively, shorten the hill for a more intense grade and less traffic. Start at Highland Ave to gain 163ft at 8.2% grade.

Honorable Mention: Nearby, Menotomy Park offers trails and hills to avoid traffic.

Bear Cage (Roxbury) – Strava Segment

Distance: 0.17 miles Elevation Gain: 52 feet Grade: 5.8%

Short and sweet, Bear Cage is infamous in the Boston Cross Country scene. Local 5k and 8k races will feature this nifty little trail hill. Follow a dirt-gravel trail starting at Pierpont Road near White Stadium. Hang to the left when you get to the top. You’ll notice abandoned structures that used to cage bears for the Franklin Park Zoo, which is how the hill was named.

Spring Hill (Somerville) – Strava Segment

Distance: 0.25 miles Elevation Gain: 87 feet Grade: 6.5%

Sorry Somerville, you are my least favorite neighborhood to run in. That doesn’t mean you don’t have a few nice hills! Start at the base of the hill on Lowell Street and Somerville Ave. Do you see how the road goes up? Run on the right side of the road until you reach the park awaiting your arrival.

Honorable Mention: Prospect Hill and Winter Hill are also popular spots. Summer Street will provide a most gentle ascent.

Wright’s Tower (Medford / The Fells) – Strava Segment

Distance: 0.16 miles Elevation Gain: 120 feet Grade: 13%

TRAILS! This is a technical, type II fun ascent. Park your car at Bellevue pond and enter the park via the wide trail to the right of the pond. After the pond, take the first right, which will be marked by a white blaze. This is the beginning of the hill. Follow the white-blazed trail to the top where you get a spectacular view of the skyline!

A view of the Boston Skyline from Wright
Beautiful views await those who climb hills

Savin Hill (Dorchester) – Strava Segment

Distance: 0.08 miles Elevation Gain: 68 feet Grade: 14.6%

Start at Savin Hill Ave and Caspian Way. At 0.08 miles, you’re basically already there. Tell that to your butt as it tries to defy gravity during this steep climb! Great for short burst workouts to build muscular strength.

Prospect Hill Park Auto Road (Waltham) – Strava Segment

Distance: 0.82 miles Elevation Gain: 341 feet Grade: 7.9%

In terms of epic Boston hills, this is second only to the Great Blue Hill in terms of magnitude. This route has you starting from Totten Pond Road and running the auto road to Prospect Hill. You have a long steady climb ahead of you. Is this fun yet?

Additionally, there is a decent network of trails allowing for you to run a variety of routes.

Bunker Hill St (Charlestown) – Strava Segment

Distance: 0.26 miles Elevation Gain: 83 feet Grade: 5.8%

Begin at the intersection of Main St and Medford Street. One direction is uphill. That’s the one for you! Be aware of cross traffic, run on the West side of the road. Finish at the Catholic Church at the top. Hallelujah!

Hospital Hill (Quincy) – Strava Segment

Distance: 0.45 miles Elevation Gain: 107 feet Grade: 4.5%

Start at Dixwell Ave and Whitwell Street. The climb is a good one that increases in grade about halfway through, giving you an extra burning sensation in the legs. That is normal. Finish at the library.

Best Running Hills in Boston

That concludes my list of the Best Running Hills in Boston. Do you feel inspired? Go, get out side and have some fun. Running is about the journey, not the destination. And running hills is certainly a ‘journey.’

A big thank you is due to friends in The Heartbreakers Running Club and Trail Animals Running Club who offered a lot of advice. If you loved my list or want to contribute, comment below. I will happily update certain neighborhoods if a hill is missing.

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This Post Has 3 Comments

  1. Brandon

    Great list, Joe! Finding the best hill for a particular workout is definitely an exercise in patience and pain – but when you Goldilocks your way there and find it…Sweetness. Looking forward to the next article!

  2. Carlos

    Great compilation! I’m interested in your honorable mention for a weekend vert vacation within reasonable driving distance from Boston. franconia notch? Entire Pemi? Maybe something less choked with people?

    1. Avatar photo
      Joe McConaughy

      The Pemi Loops is great. Start at Lincoln Woods at or before sunrise so you can pass Franconia before the throngs hit. 10,000ft of elevation is no joke! Mt. Watatic is great, and if you’re looking for something longer with vert you can do that Wapack Trail. Additionally, Wachusett Mountain and the Berkshires have a variety of options!

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