Trail Sisters Half Marathon & 10k

September 14th • Buena Vista, CO

Where to Run in Boston, Massachusetts

Jackie St. Louis is a trail and ultra runner, rock climber, and molecular biologist based just outside of Boston, Massachusetts. She enjoys the opportunity to have one foot in the city and the other in the outdoors, and is proud to be a weekend warrior of the trails or crag.

Share This Article!

In the city of champions, it’s perhaps no surprise that there is a large running community here in Boston. Maybe you’ve heard of a little annual race here called the Boston Marathon? While a majority of folks are pounding the pavement throughout the city – and admittedly, one of my favorite trails to run and bike along is pavement – there are a few trails just outside of the city where a smaller community of runners are drawn to play. While most of the local trails here contain “hills” and not mountains, don’t let their short stature fool you! The northeast packs quite a punch into a few hundred feet with it’s technical, steep and rocky ascents and descents. You’ll have a hard time drifting off into your head on a few of these trails, as you’ll need to be looking for foot placements, but these trails are a great way to train for larger objectives by making you stronger and more confident on techy terrain!

Middlesex Fells Reservation: Skyline Trail Loop

 7.6 miles, 1000 feet elevation gain


Sunrise from the Skyline Loop at Middlesex Fells.

The trail: just north of the city, and accessible without the need for a car. The Skyline Trail Loop circumnavigates the North, Middle and South Reservoirs of Winchester, MA. The trail is varied with sections of single track, some rocky climbs and descents, and spots where it widens into a fire road at intersections with other trails. There are great spots to catch a sunrise or sunset on some of the high points throughout the loop, and Wright’s Tower offers a view of the Boston skyline from the North Reservoir. Sometimes I think this trail can be cruel in sections – it makes you do a technical climb just to take you right back down practically where you started. But if you are a true city-dweller without access to a vehicle, this is a great loop to run to get in some technical training as well as some elevation!

Brews nearby: a short 10 minute drive will get you to one of my favorite breweries in the city – Night Shift Brewing. When it’s busy, parking can be tough, but the brews are worth the effort! The space is large and open with lots of seating, rotating food trucks outside to satisfy that post-run hunger, and an outdoor seating area to cool down with your pint and enjoy the sunshine.

Minute Man National Park: Battle Road Trail

9 miles out and back, 380 feet elevation gain


Wooden bridge along Battle Road Trail.

The trail: While Battle Road Trail is a relatively flat trail, mostly on a packed gravel road, this is one that is not to be missed! Along the trail you’ll find yourself following the path that Paul Revere took on his Midnight Ride, as well as his capture site. You’ll also pass by the locations of several skirmishes between the British troops and the Colonial militia. If you make it out to the park for an early morning run, you may find yourself alone on this trail, giving it an eerie yet stoic vibe.

Nearby coffee: Only a mile or so from the park, tucked in the heart of Concord’s historic downtown is Haute Coffee shop. All home-made, from scratch baked goods and pour over hot coffee, this place is a haven for cyclists, locals, and those who enjoy a great cup o’ joe.


Blue Hills Reservation: Skyline Trail Loop

12 miles, 2700 feet elevation gain


View of Boston skyline from the summit of Buck Hill.

The trail: Being that Boston is a city located right at sea level, there aren’t many spots close by where you can get much elevation training done. This trail, however, is a great way to squeeze some solid hill work in! As an out-and-back, the Skyline Loop at Blue Hills will not only make you go up AND down, but it’s also quite technical and rocky, which is a great resource if you’re doing a large portion of your training within the city limits on pavement. Located south of the city, the trail offers several wonderful views of the Boston skyline as well as varied terrain along fire roads, pine needle covered paths, and steep rocky scrambles. The nice part is that you can build up your elevation endurance slowly. There are several flat trails at the bases of most of the hills to bail on and get back to the parking if you are feeling the burn!

Nearby brews: Skip over to Canton to Trillium Brewery after a day on these trails to enjoy one of their Permutation series small batch brews or one of their clever fruity sour ales with the perfect amount of sweet and tart (my personal favorites is the Peach Fated Farmer….yum!). Or if you like something a little more rich, the Peanut Butter PM Dawn is a stout with cold brewed coffee that is sure to rejuvenate you after the tough, rocky hills in Blue Hills Res.


Charles River: Bike Path Loop

23 miles, 400 feet elevation gain


The view from Longfellow Bridge.

The trail: The Charles River Bike Path Loop is primarily used as a bike path, the entire loop is paved. There are several sections that offer a small dirt path that runs parallel to the paved part and gets you a closer view of the Charles River. There are many bridges along the loop, so you can weave your way back and forth to spice things up and gain a bit of extra elevation along the way. The views of the skyline are stunning and in my opinion, never get old, so if you are limited to the city limits due to lack of a car or bike, this path is a wonderful way to do longer training runs!

Nearby coffee & brews: There are endless places to stop along this trail – on either side of the river – for a bite to eat, cup of coffee or pint of craft beer. My favorite place is in Cambridge at Lamplighter Brewing Co. This location is small, but has such a delightful charm. If you enjoy getting a coffee and beer all in one cup, try their Cuppa – a British ale with cold brewed coffee and an under 5% alcohol content, it really hits the spot after a run. Their Helles lager after a run is also light, and very refreshing.

Boston is an historic town, so don’t forget to check out some of the sites downtown along the Freedom Trail, catch a Red Sox game at Fenway Park, or take a cruise around Boston Harbor aboard Old Ironsides, also known as the USS Constitution. Grab a bowl of clam chowdah, some fresh oysters and a lobstah roll (ask for it warm! GAME CHANGER!) at Neptune Oyster or the Saltie Girl, and finish it off with an Italian cannoli from Mike’s Pastry! I promise, you won’t be disappointed.

About the Author

Jackie St. Louis is a trail and ultra runner, rock climber, and molecular biologist based just outside of Boston, Massachusetts. She enjoys the opportunity to have one foot in the city and the other in the outdoors, and is proud to be a weekend warrior of the trails or crag.

Share This Article!

Read More


Leave a Reply

Your email address will not be published. Required fields are marked *

Join Now

Team Trail Sisters

Sept. 14th 2024

Buena Vista, Colorado

Half-Marathon & 10k

Shop & Support