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Boston · United States

Cycling & running events in Boston, 2026

490events this year

490 races within 80 km of Boston

Road, trail, gravel, MTB — you name it, we've got it. Find something worth telling your friends about.

With over 85,000 events in 2026, we have the largest endurance event database on the planet — built to be the fastest way to find a race near you.

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Top events

A few races to know in Boston

We all need a goal — why not think big? Pick one and start training for it. Already happened this year? Find some practice races to build toward next year's edition.
Run·Road
Boston

Miles for Migraine - Massachusetts

Miles for Migraine - Massachusetts takes place in July at Boston's Carson Beach. The event features a timed 5K run, a 2-mile walk, and a Relax option for those who prefer not to race. Participants will gather at the Mother's Rest Area for a morning start. This event supports migraine and headache awareness, with funds directed towards treatment, research, and Miles for Migraine's programs and services. The 5K run is professionally timed. The Walk and Relax options are free, though donations are welcome. The day will also feature speakers, sponsor booths in a festival area, finisher medals for all participants, and a prize for best purple attire. The event aims to unite the local migraine and headache community, serving as both a support gathering and a beachside race morning.

Road
Run·Xc
Boston

Trail Run 9/3

Trail Run 9/3 focuses on trail ultras and shorter trail races centered on dirt, rocks, climbing, and extended time outdoors. The most notable event is the Twisted Branch Trail Run, a 100K in the Finger Lakes Region of upstate New York. It begins at 5 a.m., sending runners into the woods before dawn. The Texmas Trail Run offers a Texas edition at Buescher State Park in Smithville, with distances ranging from 1 mile to 104K, including a four-person relay for the longest distance. Twisted Branch is the more challenging mountain-style run, covering approximately 64.5 miles with six major climbs, three exceeding 1,000 feet, and around 11,000 feet of elevation gain. Texmas utilizes repeated loops on narrow paths and singletrack, featuring rocky sections and smaller inclines, with about 450 feet of climbing and descent per loop. The 104K participants complete nine loops, while those in the 57K, 21-mile, 14-mile, and 7-mile races run fewer laps from the same start-finish point. Texmas limits participation to 500 runners and features Texas-themed aid stations stocked with drinks, sweets, salty snacks, PB&Js, bean burrito rolls, fruit, bandages, and Vaseline.

Xc
Run·Road
Boston

Fifteenth Charles River One Mile Swim

The Charles River One Mile Swim is a one-mile open-water race in Boston. It starts and finishes in the water at The River Dock near the Arthur Fiedler statue by the Hatch Shell on the Esplanade. The race takes place in early June, begins in the morning, uses chip timing, and is open to swimmers age 18 and older. It is part of the United States Masters Swimming New England Open Water Swim Series. Swimmers can earn a series prize by completing five of the seven listed swims. The course is a loop on the Charles River between the Harvard and Longfellow bridges, with the Esplanade alongside much of the swim. The Charles River Swimming Club organizes the event. This club was formed to organize competitive swims and support public swimming in the river. Its first one-mile race in the Charles basin was the first sanctioned public swim there in more than 50 years. The event acknowledges the river cleanup work that began in the mid-1990s. The race often fills up, and volunteers help make the small, tightly managed swim function.

Road
About cycling & running in Boston

Boston Base Miles And River Loops

Running: Boston runners use the Charles River paths, Comm Ave, Fresh Pond, Mystic Lakes, and Battle Road Trail. The Charles River paths keep long runs easy because they have limited road crossings, bathrooms, water fountains, and very little elevation change. Comm Ave through the Newton Hills gets busy every weekend with solo runners, training groups, and make-shift aid stations. The Heartbreakers, Trail Animals Running Club, BAA, November Project, Boston Bulldogs Running Club, Cambridge Running Club, and Heartbreak Hill Running Club give the week structure. The 11th Annual Run for Recovery 5K and Race to Cure Sarcoma Boston sit on the local calendar.

Cycling: Charles River Wheelers and CRW anchor the riding scene with hundreds of rides, a Ride With GPS club account, and a deep route library. Locals roll the Charles River paths, Minuteman Bikeway, Charles River loop, and Boston Marathon Course for steady Z2. The Boston Marathon Course runs 7 km with 220 m elevation through Newton, Wellesley, and Natick. Middlesex Fells Gravel Bike Route from Somerville runs 44 km with 489 m elevation and gives you gravel close to Somerville. Tip2Tip Quincy Gravel Mixer gives water views around Quincy Bay. Heartbreak Hill, Summit Ave, Comm Ave, and the Newton Hills hold the climbs.

Season: Fall in New England is the best time of year, with warm days, cool nights, and foliage that makes base miles feel easy. Summer keeps the Charles River paths useful because water fountains are available during the summer. Fresh Pond also helps in summer because water fountains sit on the loop and the ranger station has restrooms and water from 7 a.m. to 5 p.m. year round. Winter changes the feel for both sports because daylight gets short, rain or snow becomes more likely, and thirst response drops in colder weather. Cyclists change tires for better grip, and runners keep intervals simple when surfaces get slick.

Upcoming

Coming soon in Boston

All races within 80 km, sorted by date. Click any event for the route, registration link, and past results.
Popular elsewhere · next 30 days

What runners & riders are signing up for

If you're traveling — or just curious — here's where the action is across two of the most active markets on TrainerDay.