Shore2Shore

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• Nassau Suffolk Trail Marathon & 15 Miler [runsignup.com]

  Sun, May 17, 2026 at 7:30 AM

  Description

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  Long Island has a rich and deep running culture. There are multiple events every weekend to choose from. However, runners that enjoy longer race distances or trail events have only a few options to...

  Long Island has a rich and deep running culture. There are multiple events every weekend to choose from. However, runners that enjoy longer race distances or trail events have only a few options to choose from over the course of the entire year. This event will provide an opportunity for those that enjoy ultra or trail running to participate in a great event. A portion of the proceeds will benefit the Long Island Greenbelt Trail Conference, who help maintain the trails on Long Island.

  23.5 km from Town of Smithtown
  99 Quaker Meeting House Rd, Plainedge, New York, 11735, United States
  OpenStreetMap Google Maps

  15 Miles 26.2 Miles Marathon Run Trail Ultra

• ENDURE- Last Man Standing [runsignup.com]

  Sat, May 30, 2026 at 6:00 AM

  Description

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  ENDURE – Last Man Standing is a Long Island endurance running event using a Last Man Standing format. Runners complete a fixed 4.2-mile loop every hour, on the hour. Finish the loop within the hour,...

  ENDURE – Last Man Standing is a Long Island endurance running event using a Last Man Standing format. Runners complete a fixed 4.2-mile loop every hour, on the hour. Finish the loop within the hour, and you earn the chance to start again. Miss the cutoff or decide you’re done, and your race ends. The event continues until one runner remains or the event time window concludes. To amp things up, every few hours we will lower the time cut-off.

  The course will use designated park trails and/or park roads with a centralized start and finish area and aid station. Exact venue and course details will be shared once park permits are finalized.

  22.9 km from Town of Smithtown
  Plainview Road & Manchester Dr, Bethpage, New York, 11714, United States
  OpenStreetMap Google Maps

  4.2 Miles Last Man Standing Run Trail

• SUFFOLK COUNTY MARATHON [suffolkmarathon.com] [Register at runsignup.com]

  Sat, Oct 17, 2026 at 12:01 AM

  Description

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  The 12th Annual Suffolk County Marathon, Half Marathon, 10K, Sunday, October 18th, and the 5K will be held on Saturday, October 17th, 2026.

  Sunday's races will start in the Village of Babylon and...

  The 12th Annual Suffolk County Marathon, Half Marathon, 10K, Sunday, October 18th, and the 5K will be held on Saturday, October 17th, 2026.

  Sunday's races will start in the Village of Babylon and Finisher in Gardiner Park, located at Montauk Hwy W, Bay Shore, NY 11706. Athletes running the Half & Full Marathon will run one of the most scenic courses on Long Island, as they cross the Robert Moses Causeway. Saturdays races will start and finish at Gardiner County Park.

  Each year, the Marathon raises money to benefit veterans and to date, the Suffolk County Marathon has raised over $1,000,000 for local veterans’ services.

  17.9 km from Town of Smithtown
  Bay Shore, New York, 11706, United States
  OpenStreetMap Google Maps

  1k 3.1 Miles 6.2 Miles 9.3 Miles 13.1 Miles 16.2 Miles 26.2 Miles 29.3 Miles Marathon Run

• ROB'S TRAIL RUN EDITION [runsignup.com]

  Sun, Nov 29, 2026 at 9:00 AM

  Description

  ROB'S TRAIL RUN EDITION

  Race 5K through the trails at Stillwell Woods Preserve, located in Woodbury, NY. This Race will benefit THE CENTER FOR DEVELOPMENTAL DISABILITIES.

  Rob’s Run is dedicated to the memory of Rob Lauterborn, an extraordinary human being, talented runner. Rob was a member of the Plainview-Old Bethpage Road Runner's Club

  20 km from Town of Smithtown
  72 S Woods Rd, Syosset, New York, 11797, United States
  OpenStreetMap Google Maps

  5k Run Trail