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11 events in Windham County, Vermont

From big races to Saturday morning group runs—find running, cycling, triathlon, and swimming events and connect with the local endurance sports community.

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  • Starlit Snowshoe Hike presented by icebreaker at the Nordic Center [runsignup.com]

    Sun, Feb 15, 2026 at 7:00 PM

    Description

    Starlit Snowshoe Hike presented by icebreaker

    A Guided Snowshoe Hike at the Stratton Nordic Center

    Looking for a fun way to get on the snow after the lifts stop spinning and the stars shine bright in...

    Starlit Snowshoe Hike presented by icebreaker

    A Guided Snowshoe Hike at the Stratton Nordic Center

    Looking for a fun way to get on the snow after the lifts stop spinning and the stars shine bright in the southern Vermont sky? Look no further. We teamed up with Icebreaker, the official base layer of Stratton Mountain, for this family-friendly (10+) guided snowshoe hike. The hike will take place from 7-8:30pm at the Nordic Center, which is located in the Sun Bowl Area of the resort. icebreaker has provided 25 beanies (men) and 25 headbands (women) for the first 50 guests who sign up. After your hike has concluded, hang out, get warm by the fire, and enjoy complimentary hot drinks and s'mores. Sign up includes (1) guided hike and (1) pair of rental snowshoes.

    Family Sign Up Promotion: Sign up as a family! One child between the ages of 10 and 17 is FREE with each adult sign-up. One child 10-17 is free with one paying adult. If signing up together, please use the Adult Sign Up options and the $0 child option. If signing up a Child only participant, please use the $49 option.

    • 7 - 8:30PM

    • Fire with smores and hot drinks

    • Multiple guides

    • 10-20 guests per guide

    • Approximately 3 to 4 mile loop based on exertion comfort

    • Limited amount of icebreaker beanies and headbands for registrants while supplies last

    3 Miles

    41 Sunbowl Road, Windham County, Vermont, 05360, United States
    OpenStreetMap Google Maps
  • Kids Night Out 2/15 [runsignup.com]

    Sun, Feb 15, 2026 at 6:30 PM

    Description

    Drop your kids off for a fun night of crafting creating a winter glow lantern and a Nordic hike under the stars. All equipment provided, kids must be between the ages of 7 and 13. Location will be...

    Drop your kids off for a fun night of crafting creating a winter glow lantern and a Nordic hike under the stars. All equipment provided, kids must be between the ages of 7 and 13. Location will be the 3rd floor of Sun Bowl base lodge. Please be prompt with pickup.

    Kids must be dressed appropriately in winter gear to participate in the hiking portion. This will require a moderate amount of exertion.

    Kids

    43 Sun Bowl Rd, Windham County, Vermont, 05360, United States
    OpenStreetMap Google Maps
  • Kids Night Out 2/28 [runsignup.com]

    Sat, Feb 28, 2026 at 6:30 PM

    Description

    Drop your kids off for a fun night of crafting and tubing! All equipment is provided, and participants must be between the ages of 7 and 13. The event will take place on the 3rd floor of the Sun Bowl...

    Drop your kids off for a fun night of crafting and tubing! All equipment is provided, and participants must be between the ages of 7 and 13. The event will take place on the 3rd floor of the Sun Bowl Base Lodge. Please plan to arrive about 10 minutes early for check-in, and be prompt for pick-up at the end of the event.

    Kids must be dressed appropriately in winter gear to participate in the tubing portion. This activity will require a moderate amount of exertion.

    Kids

    43 Sun Bowl Rd, Windham County, Vermont, 05360, United States
    OpenStreetMap Google Maps
  • HOMESICK Snowboard and Culture Festival [runsignup.com]

    Fri, Mar 20, 2026 at 8:30 AM

    Description

    Stratton Mountain and East Street Archives join to celebrate the history, tradition and progression of a sport that got its start right here at Stratton, Vermont. HOMESICK is back for its fourth...

    Stratton Mountain and East Street Archives join to celebrate the history, tradition and progression of a sport that got its start right here at Stratton, Vermont. HOMESICK is back for its fourth season on southern Vermont's highest peak from March 20-22, 2026. Three days of events with legends, pros, up-and-comers, and YOU. Sign up for one, sign up for them all, and send it all weekend with the best in class.

    Spectate the on-snow events, get nostalgic and share stories in The Dawning Exhibit, send it at the Welcome Party, ride demo snowboards, get your East Street Archives book signed by the biggest names in the game, and après with live music and legends of the sport.

    A valid lift ticket or season pass is required to ride all lifts or Gondola during HOMESICK.

    Age Divisions

    MEN & WOMEN

    • 16 & Under

    • 17 - 25

    • 26 - 39

    • 40 - 49

    • 50 & Over

    Register now, spots are limited.

    Each event will be broken up into Male/Female and age categories.

    Registered riders will be able to purchase a discounted lift ticket this year AT REGISTRATION Check-In. A valid Lift Ticket or season pass is required for EACH day of competition.

    Zebulon Rail Jam Under the Lights - Friday, March 20

    Stratton Mountain School grad, XGames Gold Medalist and snowboarding superstar Zeb Powell will be back in 2026 to design and host the Planet Zebulon Rail Jam. Jib with the pros in this jam style format on the bottom of Suntanner. You won’t want to miss this event, brought to you by East Street Archives and Planet Zebulon. This event will start on Friday during the day, with Finals happening under the lights.

    Powers Retro Pipe - Saturday, March 21

    The Stratton Parks Crew will cut the Powers Retro Pipe on East Byrnes Side, scene of landmark events in the 80's and 90's. Olympic medalist Ross Powers is back for his fourth year of setting the tone for his signature halfpipe event. HOMESICK has seen dozens of legends return to the Stratton halfpipe along with local and regional rippers. HOMESICK 2026 is set to be another historic gathering of riders at Stratton in March. Be sure to register early, and who knows, you may find yourself at the top of the halfpipe getting ready to drop in with Ross, Shannon Dunn, Jeff Brushie, Shaun White, and Tina Basich, next to you.

    OG Downhill - Sunday, March 22

    Before there was a halfpipe, slopestyle or rail jams... snowboard events were all downhill. Here's your chance to strap in like it's 1983 - the year Stratton first welcomed snowboarding. This dual slalom race includes gates, rollers, and many turns on a red and blue course down Suntanner. Race your gear with a run on each course, sending it sideways on your board just like the snowboard contest pioneers did when and where it all began years ago.

    You will need a valid season pass or lift ticket in addition to registering for the event.

    Discounted tickets will be available at Guest Services on the day for registered competitors only. Guests can purchase the lift ticket for DAY THEY ARE COMPETING ONLY for 35.00 + tax. at inside ticket window.

    Run

    Windham County, Vermont, 05155, United States
    OpenStreetMap Google Maps
  • Stratton Pond Skim [runsignup.com]

    Sat, Mar 28, 2026 at 11:00 AM

    Description

    It's time to Sink or Skim. Try not to take a dip during the Annual Pond Skim at Stratton on Saturday, March 28th. Participants will try to skim across the water's surface and make it out the other...

    It's time to Sink or Skim. Try not to take a dip during the Annual Pond Skim at Stratton on Saturday, March 28th. Participants will try to skim across the water's surface and make it out the other side just as dry as they entered. This event is just as fun to watch as it is to enter. Join us to see who sinks and who skims.

    Come ready to skim the pond on your skis and snowboards, dressed in your favorite costume. We'll select multiple winners who will be judged on Best Costume, Best Crash, and Best Skim. Online Registration is open to the first 150 participants. Each Pond Skim participant will receive a 2026 Giveaway. Lift tickets for participants without a season pass will be sold for $45* plus tax at check-in on the day of the event.

    All participants must wear helmets for their runs, or they will be turned away. Participants must go down individually; for safety, no double skis, pulling items, or ski poles are allowed. Breaking any of these rules will disqualify participants with no refunds.

    Participants will be allowed to purchase a discounted ticket on the day of the event at the ticket window. All participants must have a valid season pass or lift ticket to participate.

    *Price is subject to change

    Run

    5 Village Lodge Road, Windham County, Vermont, 05155, United States
    OpenStreetMap Google Maps
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