Photo: Roy Luck · CC BY 2.0
Pittsburgh · United States

Cycling & running events in Pittsburgh, 2026

268events this year

268 races within 80 km of Pittsburgh

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 Pittsburgh

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
Pittsburgh

Run Around the Square

Run Around the Square is a neighborhood race in Regent Square, Pennsylvania, offering a 5K and a 1.5-mile run/walk. The shorter event begins the morning, followed by the 5K. Packet pickup is available the evening before and the morning of the race. The 1.5-mile option is a more relaxed, family-friendly part of the day. The 5K is a sanctioned race with specific rules: no strollers, no animals, and dogs are not permitted in that event. The 5K starts with about a mile on Regent Square streets, then enters Frick Park on cross-country trails and finishes in Fern Hollow. Runners will also cross the Fern Hollow Bridge, staying on the sidewalk. The 1.5-mile run/walk remains on Regent Square streets, and leashed family dogs are welcome if each dog has a registered owner or handler. Children 13 and under can earn awards in the 1.5-mile event, provided they finish the course unassisted. Toddlers in strollers do not qualify for awards.

Road
Run·Road
Pittsburgh

DICK'S Sporting Goods Pittsburgh Marathon Weekend of Events

Listed in our event index as 2025 DICK'S Sporting Goods Pittsburgh Marathon.

Road
Run·Road
Pittsburgh

UPMC Health Plan Pittsburgh Half Marathon Walking Division

One of Pittsburgh's recurring annual races.

Road
About cycling & running in Pittsburgh

Pittsburgh Training Notes

Running: Pittsburgh runners live on river miles, park loops, and hills that show up fast. Locals stack Z2 on the Three Rivers Heritage Trail, the South Side Riverfront Trail, the Eliza Furnace Trail, and the GAP trail when they want steady footing. Fleet Feet Pittsburgh keeps the week simple with Recovery Runs at Fleet Feet Bakery Square on Mondays at 6:30 PM, Track Club at Schenley Park Oval on Wednesdays at 6:30 PM, East End Pub Runs on Thursdays at 6:30 PM, and Long Runs on Sundays at 7:30 AM. Pittsburgh Pharaoh Hounds Running Club meets Tuesdays at 6:30 PM at the Schenley Oval. North Park lake gives about 5 miles per loop with short hills, long hills, and flat parts. Frick Park is big enough for a get-lost long run. The anchor races are DICK'S Sporting Goods Pittsburgh Marathon Weekend of Events, EQT Pittsburgh 10 Miler, The Big Run 5K, and Run Around the Square.

Cycling: Pittsburgh riding feels better once you stop fighting the map. The city has over 117 miles of marked bike routes, and the rivers make easy links from Oakland over the Hot Metal Bridge into Southside, along the GAP trail to the Point, and back by the sister bridges. Mt. Lebanon Cycling & Caffeine Club has been bicycling the roads and trails of Pittsburgh and beyond since 1988, and it rides over Mount Washington every Saturday morning. Flock of Cycles usually rolls out of Oakland, Major Taylor Cycling PGH runs a Wednesday no-drop city tour of 12 to 18 miles, and Pittsburgh Randonneurs handles 100 to 600 km work. Allegheny Cycling Association gives you Tuesday and Wednesday evening racing at the cycling oval. Pittsburgh Masters Velo Club makes Friday Night at the Track a summer anchor. The climbs sit on Mount Washington, North Park's Big Hill, and the steep two-lane roads between neighborhoods.

Season: Pittsburgh gives runners and cyclists the best rhythm in spring and fall, when mild weather makes intervals, long runs, and base miles feel clean. Summer brings warm, humid days, but it also brings the most sunshine, so locals start early, carry fluids, and use river trails before the heat index builds. July is the warmest month, and the city still works if you respect the hour. Winter changes the kit more than the attitude. Cold, snowy weeks push runners toward cleared paths, Schenley Park Oval, and steady Z2, while riders split time between weekend road rides, track sessions, and singletrack when Frick Park or Hartwood Acres Park is in shape.

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Coming soon in Pittsburgh

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.