Photo: Pierre André Leclercq · CC BY-SA 4.0
Watertown · United States

Cycling & running events in Watertown, 2026

31events this year

31 races within 80 km of Watertown

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

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Top events

A few races to know in Watertown

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
Watertown

1812 Challenge Weekend

The 1812 Challenge Weekend is a Saturday-to-Sunday race series held at Sackets Harbor Battlefield in Sackets Harbor, New York. Saturday features shorter races: a children's run, a 5K, and a 5-mile race, all starting and finishing at 1812 Brewing Company. Sunday offers longer distances: a half marathon and the 18.12-mile Challenge. The format allows runners to participate in multiple races over the weekend. The Patriot Challenge combines the 5K with the half marathon. The Victory Challenge pairs the 5K with the 18.12-mile race, and the Liberty Challenge links the 5K and 5-miler. The ultimate option is the Freedom Challenge, including the 5K, 5 miles, and 18.12 miles, totaling a marathon distance. Runners completing one of these multi-race challenges receive an additional medal or pin. The event has run for over ten years.

Road
Bike·Road
Watertown

Tour de Lewis

Listed in our event index as Tour de Lewis: 2026.

Road
Bike·Gravel
Watertown

North Winds Gravel Classic

The North Winds Gravel Classic is a timed gravel race in the remote Tug Hill region of northern New York, organized by the Adirondack Foothills Cycling Club. Participants can select from various distances, accommodating faster racers, consistent gravel riders, and those seeking a shorter ride on challenging roads. The event is known as “the fastest gravel in the Northeast,” a claim supported by its location: Tug Hill features long, well-maintained gravel roads developed for year-round outdoor activities. The event's name originates from the winds that sweep across Lake Ontario and ascend Tug Hill, the same weather phenomenon responsible for the area's numerous windmills and its status as the snowiest region east of the Rocky Mountains. The route consists of clear, secluded gravel roads, distinct from urban streets or paved cycling paths. An after-party follows the race. Proceeds from the event benefit the Adirondack Cycling Club’s All Kids Bike program, in collaboration with Encompass Recreation, connecting the race to a local initiative focused on teaching children to ride bicycles.

Gravel
About cycling & running in Watertown

Watertown-Fort Drum Training Notes

Running: Locals run Fort Drum steady, with Magrath Sports Complex and Remington Park handling a lot of 5K rhythm. The Fort Drum Army Ten-Miler Team gives faster runners a clear target, and the qualifiers at Magrath keep the pace honest. Sackets Harbor pulls people west for the Sackets Harbor Marathon & Half Marathon, the 1812 Challenge Weekend, and the Summer Solstice 5K. The route runs 95 km and gains only 15 m, so locals use it for clean pacing. The route to Watertown runs 28 km and gains 276 m when Z2 needs bite.

Cycling: Locals ride pavement, gravel, dirt, stone, wooded trails, singletrack, country roads, and rolling hills. JeffCoBiking keeps the road and gravel crowd plugged in, while Rec & Res Bike Studio and Black River Adventures anchor the Watertown bike scene. The Watertown loop runs 6 km and gains 89 m for base miles close to town. The Fort Drum loop is 6 mi. Tug Hill holds the harder climbs, and JeffCoBiking calls them hill climbs for fun, training, and competition. Ward Hill Mountain Bike Trail brings designated singletrack.

Season: May, June, July, August, and September give runners and riders the best block for intervals, long Z2, and anchor events. June stacks the 1812 Challenge Weekend and Bikes, Brews, and Burgers Poker Ride, while July brings the North Winds Gravel Classic in Rodman and August brings Winona Forest Backyard Ultra energy. Summer opens up Lake Ontario routes, Guffin Bay, Sawmill Bay, Chaumont Bay, and country roads. Winter shifts the mood toward Fort Drum 5Ks and the Holiday Triple Crown Run Series, with Spooky Dash, Turkey Trot, and Ugly Sweater 5K carrying the calendar.

Upcoming

Coming soon in Watertown

All races within 80 km, sorted by date. Click any event for the route, registration link, and past results.
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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.