Boston

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Boston offers an exceptional variety of running routes that blend urban beauty, historic charm, and easy access to nature, making it not just a great place to run, but a city that truly lives and breathes the sport. The Charles Riverfront serves as the city’s signature route, with miles of paved paths ideal for everything from daily jogs to marathon training. Extending south from the city center, the historic Emerald Necklace links a series of green spaces, from Boston Common through the Back Bay Fens to Jamaica Pond and Franklin Park, providing a shaded, continuous escape that showcases Boston’s lush park system.

Outside the city limits, neighboring towns like Cambridge and Somerville add their own character to the region’s running landscape. For those seeking elevation and rugged terrain, the Middlesex Fells Reservation to the north and the Blue Hills Reservation to the south deliver technical trails, steep climbs, and sweeping vistas, proving that Boston’s running opportunities extend far beyond its iconic streets.

This rich tapestry of routes supports one of the world’s most storied and passionate running communities. Every April, the city becomes the global epicenter of the sport with the Boston Marathon, the oldest and most revered race in existence, embodying Boston’s enduring spirit and worldwide appeal. Locally, countless run clubs cater to every pace, personality, and neighborhood, fostering a deeply rooted culture of camaraderie and dedication. As both a cultural and commercial hub for running, Boston is home to leading running brands like New Balance and Tracksmith, as well as the locally owned Heartbreak Hill Running Company, a store and gathering space that reflects the city’s profound pride in the sport.

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City Runner’s Pick

ROUTES

Charles Riverfront is Boston’s premier running destination. A scenic multi-use path stretches for miles along both banks of the river, offering walkers, runners, and cyclists picturesque views through Boston and its neighboring communities.

The most popular stretch runs between Boston and Cambridge, where several bridges create endless loop possibilities. West of Boston University, the river narrows as the path winds through Cambridge, past Harvard, and onward through Allston, Brighton, and into Watertown.

A scenic jog along the river between Boston and Cambridge can be anywhere between 3 to 7 miles. A classic Boston-to-Watertown loop covers about 17 miles, perfect for long runs.

Distance: up to 17 miles out and back.
Profile: mostly flat, some street crossings.
Route Map: Strava

Charles Riverfront

The Emerald Necklace is a chain of interconnected parks, parkways, and waterways designed by famed landscape architect Frederick Law Olmsted in the late 19th century. Winding through its lush greenery are quiet, tree-lined multi-use paths that offer a serene escape from the city’s bustle.

This verdant corridor has long been a favorite among local runners, delivering shaded, scenic routes ideal for everything from easy jogs to long training runs, all within Boston’s urban core. One-way from Boston Common to Franklin Park spans about 7 miles, with plenty of options to shorten or extend your run along the way.

Distance: up to 18 miles out and back.
Profile: mostly flat, some street crossings.
Route Map: Strava

Emerald Necklace

Arnold Arboretum is a living museum of trees and woody plants, it is home to over 16,000 plants representing more than 2,100 species, including world-renowned collections of lilacs, maples, and crabapples. The arboretum is free and open to the public year-round.

A network of paved paths winds through rolling hills, providing a scenic setting for walking, running, or cycling. One of the arboretum’s highlights is the incline up Bussey Hill, popular with runners for hill repeats. The arboretum also offers a peaceful network of soft-surface trails that make it a favorite for runners seeking dirt and crushed-stone paths within the city.

Website / Trail Map

Arnold Arboretum

Fresh Pond is a scenic reservoir and public park in Cambridge, just northwest of Harvard Square, offering a calm, green escape from the city.

A flat, well-maintained 2.4-mile paved path circles the water, making it a favorite among Cambridge runners, walkers, and cyclists looking for an uninterrupted loop. Along the way, you’ll get open water views, shaded stretches, wildlife sightings, and a peaceful, almost meditative vibe that feels worlds away from nearby streets. It’s especially popular in the early morning and at sunset, when the light over the reservoir is at its best.

Distance: 2.4-mile loop
Profile: flat, uninterrupted
Route Map: Strava

Fresh Pond

The Middlesex Fells Reservation is a sprawling 2,575-acre park just north of Boston, popular with runners, hikers, and outdoor enthusiasts. The reservation offers a mix of maintained trails (marked with colored paint for easy navigation), scenic ponds, and city views, with terrain ranging from flat loops to challenging climbs.

Interstate 93 divides the Fells into west and east sections. On the west side, popular routes include the Skyline Trail (7.7-mile loop, 941 ft+, white) and the Reservoir Trail (6.0 miles, 456 ft+, orange), both dirt paths winding around three reservoirs. The east side features additional dirt trails and a mostly paved 3.8-mile loop (136 ft+) around Spot Pond. The Cross Fells Trail (9.1 miles one-way, 1,069 ft+, blue) connects the east and west sections, linking different trailheads in Winchester, Medford, and Melrose.

Website / Trail Map

Middlesex Fells

MIT Track is a standard 400-meter outdoor track at Briggs Field in Cambridge. It’s one of the most popular informal track workout spots in the Boston area because it’s easy to access, centrally located, and surrounded by great warm-up/cool-down routes along the Charles River Esplanade. It is usually open to the public when not reserved for official practices or events. Many local runners and run clubs (such as Heartbreak Run, Tracksmith) drop in early mornings, evenings, and weekends for speed workouts.

Address: 250 Vassar Street, Cambridge, MA 02139

MIT Track

COMMUNITY

Heartbreak Hill Running Company is a beloved run specialty store founded in Boston. It has three retail stores in Greater Boston, fostering a strong local running community with weekly group runs and special events year-round.

Address:
652 Tremont St, Boston, MA 02118
294 Massachusetts Ave, Cambridge MA, 02139
638 Commonwealth Ave, Newton, MA 02459

Group Run Schedule:

  • Tuesday 6:34am speed workout at the Reggie Lewis Center (winter) or MIT Track (summer).

  • Thursday 6:30pm speed workout at all stores.

  • Saturday 8am long run at the Newton store.

Website‍ / ‍Instagram: @heartbreak.bos

Heartbreak Run

Tracksmith is an independent running brand founded in Boston, crafting high-quality, heritage-inspired apparel and gear for dedicated runners. The Trackhouse on Newbury St serves both as a retail space, and a community hub that hosts multiple weekly group runs.

Address: 285 Newbury St, Boston, MA 02115

Group Run Schedule:

  • Wednesday 6:30pm speed workout

  • Friday 6:30am easy miles

  • Sunday 9am paced long run

Website‍ / ‍Events‍ / ‍Instagram: @tracksmithrunning

Tracksmkith

Bricklayers Union is a running collective that blends group runs, self-accoutable workouts, social vibes, competitive racing, and creative events.

Group Run Schedule:

  • Wednesday 6:45am at BU Bridge (Boston side).

  • More runs and events announced on IG.

Instagram: @bricklayersunion

Bricklayers Union

PIONEERS Run Crew is a community-focused, inclusive running group based in Dorchester, Boston. It is created to make running equitable and accessible, particularly for runners of color and anyone looking for a welcoming run crew.

Group Run Schedule:

  • Wednesday 6:30pm in Dorchester.

  • More runs and events announced on IG.

Instagram: @pioneersrc

Pioneers Run Crew

Metro Moovin’ Run Club is a community-based social running group, welcoming runners of various paces and abilities who want to run together, socialize, and make training more fun and communal.

Group Run Schedule:

  • Tuesday and Thursday 6:30pm at Mass Ave Bridge (Boston side).

Instagram: @metromovinrc

Metro Movin’

CAFÉS

Gracenote Coffee Roasters is a beloved (and The City Runner's favorite) specialty coffee shop and espresso bar in downtown Boston, steps from South Station. It is known for precision-roasted beans and expertly crafted espresso drinks in a small, intimate, and vibrant setting.

Address: 108 Lincoln St, Boston, MA 02111

Instagram: @gracenoteboston

Gracenote Coffee Roasters

Greystone Cafe blends excellent coffee with fresh, from-scratch pastries, sandwiches and brunch dishes. Their croissants are a real highlight: light and flaky with a generous, satisfying portion, making them a favorite among regulars. The space feels warm and community-oriented, with a walk-up window for quick stops and a relaxed vibe that’s perfect for a casual morning coffee.

Address: 123 Appleton St, Boston, MA 02116

Instagram: @greystone_southend

Greystone Bakery & Cafe

Broadsheet Coffee is a standout specialty coffee spot in Cambridge, located a short walk away from Harvard Yard, with an effortlessly smart, buzzy vibe. The café’s bright, modern space, masterfully crafted coffee drinks and rotating seasonal offerings make it a favorite stop for locals.

Address: 100 Kirkland St, Cambridge, MA 02138

Instagram: @broadsheetcoffee

Broadsheet Coffee Roasters

Third Cliff Bakery is a lovely neighborhood bakery and café in Jamaica Plain, offering a variety of pastries from the classics to creative twists like guava and kimchi flavored croissants and other seasonal treats, all in an airy, friendly space.

Address: 3531 Washington St Suite 103, Jamaica Plain, MA 02130

Instagram: @thirdcliffbakery

Third Cliff Bakery

More Resources

Training Groups

  • The B.A.A. Running Club is a training community for runners of various ages and abilities, emphasizing community, training, and competition both in local races and across New England.

    The club is part of the B.A.A.’s broader running programs, which also include the Racing Team (top regional competitors) and the High Performance Team (elite/professional athletes).

    Website / Instagram: @runteambaa

  • Battle Road Track Club is a Boston‑based elite post‑collegiate running team focused on helping athletes chase personal records and team championships in cross country, track, and road racing events.

    Website / Instagram: @battleroadtc

  • Boston Hares is the community based Boston racing team of Tracksmith Running, offering weekly team workouts and year-round racing opportunities. All ability levels are welcome.

    Instagram: @bostonhares

  • Cambridge Running Club (CRC) brings together runners of all abilities, united by a shared love of the sport and a commitment to continuous improvement. The club offers two weekly runs: a coached Thursday evening track workout and a member-hosted Saturday morning long run, complemented by regular social and community events.

    Website / Instagram: @cambridgerunning

  • The Central Mass Striders is one of the largest and oldest run clubs in New England. The Striders stays deeply involved in the Central Mass running scene, it welcomes runners of all ages and abilities, organizes regular group runs and workouts, and hosts and supports a bunch of local races.

    Website / Instagram: @centralmassstriders

  • The Dashing Whippets (Boston) is the Boston chapter of the larger Dashing Whippets organization originated in NYC. It focuses on fostering camaraderie, structured training, and competitive racing among runners of varied abilities. The race team hosts three weekly runs, including Wednesday track workouts and Saturday long runs.

    Website / Instagram: @dwrtboston

  • The Greater Boston Track Club brings together post-collegiate athletes, masters competitors, and dedicated runners interested in coached training, competition, and community support. The club hosts weekly coached workouts and long runs, as well annual meets, and has a long history of competitive excellence across track & field, cross-country, and road racing.

    Website / Instagram: @gbtcrunning

  • Notch Run Club (often associated with Meters for Liters) is a community running group centered around Notch Brewing locations in Brighton (Boston) and Salem, MA. It’s a free, inclusive group open to all abilities, from casual joggers to competitive club runners. It’s built around community, social running, and fun, while also has a race team and weekly coached workouts.

    Website / Instagram: @metersforliters

Community Events

  • 26.TRUE Marathon is a community-driven, unsanctioned marathon, held the day before the Boston Marathon. It is organized by the PIONEERS Run Crew and aims to offer a more inclusive, accessible, and culturally rooted alternative to the traditional Boston Marathon, and to celebrate Boston’s diverse neighborhoods and culture.

    Instagram: @26.truemarathon

  • The Charlie Card Challenge is an unsanctioned running event where participants race against the MBTA’s Green Line B Branch train. The race starts from Boston College Station and finishes at Park Street Station in downtown Boston, with a distance of about 6 miles.

    Instagram: @rundirtywater

  • Organized by local run club Bricklayers Union, Dawn to Dusk is a continuous relay that loops around Jamaica Pond in Boston from sunrise to sunset. Usually held on a summer day, the event is a celebration of community where participants are encouraged to stay around and spectate.

  • Organized by Heartbreak Hill Running Company, Mob Mile is a community-focused timed trial for runners who want to test their speed and enjoy a lively, inclusive race atmosphere. Heartbreak also offers a 8-week training plan before the race.

Local Races

  • Boston Marathon is the world’s oldest marathon and one of the most prestigious road racing events. It's held every year on the third Monday in April, with BAA 5K happening the day before.

    Instagram: @bostonmarathon

    Boston Athletic Association, the organizer of Boston Marathon, also hosts a 10K (June) and Half Marathon (November).

  • Flat and fast, Baystate Marathon and Half Marathon held in Lowell, MA every October is popular among New England runners.

    Instagram: @baystatemarathon

  • Cambridge Half Marathon is part of the CambridgeSide race series (also including two 5Ks), and held in late October / early November.

    Instagram: @csraceseries

  • New Bedford Half Marathon is a historic, scenic, and challenging race typically held on the third Sunday in March, serving as an early-season tune-up race for many local runners.

    Instagram: @nbhalfmarathon

  • Falmouth Road Race is a 7-mile road race held each August on Cape Cod, 70 miles south of Boston. It is one of the most celebrated non-marathon races in the country, attracting elite athletes, recreational runners, and thousands of spectators every year.

    Instagram: @falmouthroadrace

  • Beach to Beacon is a 10K road race help every August in Cape Elizabeth, ME, founded by Olympic marathon gold medalist Joan Benoit Samuelson. The Point-to-point course starts at Crescent Beach and finishes at Portland Head Light (the “Beacon”), one of the most famous lighthouses in the U.S.

    Instagram: @tdbeach2beacon

  • The Harpoon 5-Miler is a popular race that combines running, community, beer, and charity, organized by Harpoon Brewery each year in May.

  • An extremely challenging uphill running event, the legendary Mount Washington Road Race is held every June on Mount Washington in New Hampshire, the tallest peak in the Northeast.

Getting Around

like the city runner

Public Transit

MBTA (Massachusetts Bay Transportation Authority) is the agency that runs the buses, subways (the “T"), commuter rail, and ferries in the greater Boston area.

Network: The subway features four color-coded lines that primarily serve Boston, Cambridge, and Brookline. Combined with an extensive bus network, this core system provides convenient access to most running destinations

The Commuter Rail covers a much broader geographic area. While it runs less frequently and has higher fares than the subway, it’s invaluable for reaching more distant areas, such as Middlesex Fells Reservation or coastal towns along the Northern Strand Trail.

Fare Payment: Fares can be paid using a reloadable CharlieCard (best for frequent riders), a disposable CharlieTicket, or contactless payment via smartphone or credit/debit card at fare gates and onboard buses.

Getting in

Logan International Airport is seamlessly connected to downtown Boston via the MBTA’s Silver Line, a bus rapid transit service that runs between all airline terminals and South Station.

South Station (in the Financial District) and North Station (in the West End) are Boston’s two primary intermodal transit hubs, connect Amtrak regional trains, subway lines, MBTA buses, and Commuter Rail services.

Bike Share

Bluebikes is the bike share program in the greater Boston area.

Plans include single ride, day pass, monthly pass, and annual pass. Bike stations are plenty and spread across the metro area, especially Boston, Brookline, Cambridge, and Somerville.