13 running events in Windsor County, Vermont

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

• Ascutney Mountain Run [runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sat, May 30, 2026 at 9:00 AM

  Description

  ▼ Show more Show less

  Course

  Route: Start at the State Park entrance, run up the paved Auto Road 3.7 miles - 2300 Vertical Feet,

  Finish at the summit parking lot.

  A USATF Sanctioned Event.

  Headphones are permitted (per...

  Course

  Route: Start at the State Park entrance, run up the paved Auto Road 3.7 miles - 2300 Vertical Feet,

  Finish at the summit parking lot.

  A USATF Sanctioned Event.

  Headphones are permitted (per updated USATF rules) but baby strollers are

  strictly forbidden in the race

  Limited parking at summit parking lot near the finish line and also the location of post race festivities (awards, food, etc). $4.00 per vehicle to drive up the auto road. First come, first served. Mt. Ascutney State Park requires dogs to be on a leash and they must have a rabies tag

  Age Groups:

  M&F 14&under, 15-19, 20-39, 40-49, 50-59, 60+

  Lodging

  Mt. Ascutney State Park - Camping at the race site, 802-674-2060

  Holiday Inn Club Vacations at Ascutney Mountain Resort - Brownsville, Reservations: 800-315-2621,: 802-484-7711 (5 miles from race)

  Snapdragon Inn - Windsor 802-227-0008 (about 5 miles from race)

  Holiday Inn Express - Springfield 802-885-4516 (about 12 miles from race)

  Windsor Motel - Windsor 802-674-5584 (about 3 miles from race)

  3.7 Miles Run

  1826 Back Mountain Road, Windsor County, Vermont, 05089, United States
  OpenStreetMap Google Maps
• CBHM for Zack's Place [zacksplacevt.org] [Register at runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sun, Jun 07, 2026 at 6:00 AM

  Description

  ▼ Show more Show less

  Known as the best 13.1 mile race in New England.

  The Covered Bridges Half Marathon was first run in 1992. Race founder David Chioffi and a group of community members got together to create a half...

  Known as the best 13.1 mile race in New England.

  The Covered Bridges Half Marathon was first run in 1992. Race founder David Chioffi and a group of community members got together to create a half marathon along some of the best running routes around Woodstock, Vermont. The course they designed was unique because of the four covered bridges along the way, two of which the runners ran through. After building a mailing list of over 4,000 names, the race had nearly 400 runners that first year.

  Like many races, the course was adjusted several times in the first few years to address traffic and parking concerns, as well as the growing popularity of the race. The current course has been in place since 1997. The popularity of the race has continued to rise, reaching 2,900 registrants in 2001.

  The race was scaled back in 2002 to 2,000 registrants in order to maintain the small feel of the race and in response to reduced parking capacity.

  The race has grown very slowly to the present cap of 2,300 runners. The on-line registration fills quickly each year, usually in a few minutes from the time that it “goes live.”

  The race is organized by a completely volunteer staff, under the corporate umbrella of CBHM, Inc., a non-profit corporation formed specifically to organize running events and donate the proceeds to charity.

  13.1 Miles Run

  73 Central Street, Windsor County, Vermont, 05091, United States
  OpenStreetMap Google Maps
• Covered Bridges Half Marathon [cbhm.com] [Register at runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sun, Jun 07, 2026 at 8:15 AM

  Description

  ▼ Show more Show less

  Covered Bridges Half Marathon - a community based RUNNING ROAD-RACE-held on the first Sunday in June and is hosted by CBHM Inc., a 501(c)(3) nonprofit organization located in Woodstock, Vermont.

  CBHM...

  Covered Bridges Half Marathon - a community based RUNNING ROAD-RACE-held on the first Sunday in June and is hosted by CBHM Inc., a 501(c)(3) nonprofit organization located in Woodstock, Vermont.

  CBHM is the best 13.1 miles in New England! Experience some of Vermont's Covered Bridges.

  Each year CBHM runners give back over $75,000 in donations to our youth groups, non-profits and local recreation departments (the people who take care of you on our race course!)

  13.1 Miles Half Marathon Run

  Windsor County, Vermont, 05091, United States
  OpenStreetMap Google Maps
• Lace Up for Laura 2026 [laceupforlaura.com] [Register at runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sat, Jun 27, 2026 at 8:30 AM

  Description

  ▼ Show more Show less

  The Lace Up for Laura 5k walk/run fundraiser and Kids' Fun Run is a way to come together the last Saturday in June each year in celebration of Laura Cody McNaughton's life and her vision to bring...

  The Lace Up for Laura 5k walk/run fundraiser and Kids' Fun Run is a way to come together the last Saturday in June each year in celebration of Laura Cody McNaughton's life and her vision to bring health and wellness to all before she died in a tragic car accident on June 28, 2018. All proceeds support local high school scholarships, and thanks to our amazing participants and sponsors, we’ve awarded $50,000 in local scholarships so far! It is intended to be a fun activity families can participate in together with runners and walkers of all abilities.

  The event will consist of two races held on Saturday, June 27, 2026 in Weathersfield, VT:

  ---->8:30am- Approximately 1/3 mile Kids' (12 and under) Fun Run with COLOR RUN stations, BUBBLE stations, and a MEDAL for all. Plus all participants will receive a complimentary commemorative LACE UP DUCK for the Springfield Area Parent Child Center Duck Run happening in Springfield at their Family Block Party and Duck Run at 4PM! Ducks will have a chance to win cash and prizes at their event. A great day for local families!

  ---->9:00am- 3.1 mile (5km) race for all ages and abilities with professional timing, music, water stations, and uplifting energy

  The starting line for both races will be located near the intersection of Plains Road and Reservoir Road. The 3.1 mile race will be an out and back race on the scenic dirt road known for its lack of change in elevation. Proceeds from the 5K will benefit the Laura Cody McNaughton Memorial fund and its annual scholarship which will be awarded to a graduating senior who exemplifies Laura’s leadership and giving spirit, and is pursuing further education and training in a field where these principles may be put into practice.

  5k Fun Run Run Walk

  Intersection Of Plains Road And Reservoir Road, Windsor County, Vermont, 05151, United States
  OpenStreetMap Google Maps
• Firecracker 5K [runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sat, Jul 04, 2026 at 9:00 AM

  Description

  ▼ Show more Show less

  Join us for the inaugural Ottauquechee River Trail (ORT) Firecracker 5K on Saturday, July 4th, 2026. Part of Woodstock’s 250th Celebration honoring the signing of the Declaration of Independence, the...

  Join us for the inaugural Ottauquechee River Trail (ORT) Firecracker 5K on Saturday, July 4th, 2026. Part of Woodstock’s 250th Celebration honoring the signing of the Declaration of Independence, the Firecracker 5K also will raise funds to support the ongoing maintenance of the Ottauquechee River Trail.

  The Firecracker 5K is family-friendly, and the route is mostly flat, easy to walk or run, and surrounded by lots of great nature! The Walk/Run will start at 9AM at the ORT kiosk in Woodstock’s 0 Maxham Meadow Way and follow the Ottauquechee River as it runs along beautiful hay fields, a vernal pool, and Woodstock’s 150-year-old rail bed.

  Sign up early! Registration is limited. Parking is available but limited, either at East End Park or Sunset Farms, so please plan to carpool, ride a bike, or walk to the event if possible. Beverages and snacks will be available after the race.

  Bring the whole family, except your dog! Unfortunately, dogs are not allowed to join the participant during the event.

  The Firecracker 5K is not to be missed!! Mark your calendar and tell your family and friends!

  5k Run Trail Walk

  0 Maxham Meadow Way, Windsor County, Vermont, 05091, United States
  OpenStreetMap Google Maps
• Ragnar Trail Vermont [finishers.com] - Facebook
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Fri, Jul 10, 2026

  Run Trail

  Windsor County, Vermont, United States
  OpenStreetMap Google Maps
• Vermont 100 Endurance Race [vermont100.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Fri, Jul 17, 2026

  100k 100 Miles Run

  411 Cemetery Road, Windsor County, Vermont, 05089, United States
  OpenStreetMap Google Maps
• Triquest Gravel Triathlon 2026 [runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sat, Sep 12, 2026 at 8:00 AM

  Description

  We are so excited for year TWO!!! Registration is open and sign ups are robust

  Race date - September 12, 2026

  Course details

  • Swim 1 mile

  • Bike 28 miles

  • Run 7.5 miles

  Event options

  • Individual Triathlon

  • Aquabike (Swim/ Bike only)

  • Duathlon (3.5 mile run / Bike / 7.5 mile run

  • Relay ( Swim/Bike/Run) but with 2-3 total team members divvying up the legs

  All entries get a T-shirt and lunch!

  28 Miles 37 Miles Aquabike Cycling Duathlon Gravel Run Swim Triathlon

  2008 Scout Camp Rd, Windsor County, Vermont, 05149, United States
  OpenStreetMap Google Maps
• Vermont 50 Mountain Bike or Ultra Run [vermont50.com] [Register at runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Sun, Sep 27, 2026 at 6:00 AM

  Description

  ▼ Show more Show less

  33 Years of Supporting Vermont Adaptive

  The Vermont 50 is an annual race held during the last weekend of September at Ascutney Outdoors in West Windsor, Vermont. All benefits go to Vermont Adaptive...

  33 Years of Supporting Vermont Adaptive

  The Vermont 50 is an annual race held during the last weekend of September at Ascutney Outdoors in West Windsor, Vermont. All benefits go to Vermont Adaptive Ski and Sports. A wonderful place where youth and adults with disabilities gain a measure of self confidence and independence by participating in adaptive sports programs and activities year-round.

  Since 1993 the Vermont 50 has been a destination for mountain bikers and ultra runners to enjoy a challenging and scenic Vermont landscape course that is like no other. There is something for everyone. We offer the Vermont 50 mile Mountain Bike Race, Womens 2-person Bike Relay, Over 60 2-person Bike Relay, 50 mile Ultra Run, 50K Endurance Run, 2-3 Person 50 mile Run Team Relay and the Kids Fun Runs and Bike Rides.

  NOTE-This race does NOT allow E-Bikes.

  We are a family friendly event offering lots of kid centered activities such as the Hay Bale Treasure Hunt, The Fun Runs and Rides, clowns, face painting and more! Join us and find out why the Vermont 50 has become so popular. (Subject to change as COVID-19 rules and regulations apply.)

  Spots fill-up quickly so early registration is a must!

  50k 50 Miles Fun Run Run Ultra

  Ski Tow Road, Windsor County, Vermont, 05037, United States
  OpenStreetMap Google Maps
• Zacks Place Thanksgiving Turkey Trot in-person and global [zacksplacevt.org] [Register at runsignup.com]
  • Subscribe to My Calendar (sign in required)

  • ---

  • Download single event

  Thu, Nov 26, 2026 at 10:00 AM

  Description

  ▼ Show more Show less

  Hi Everyone,

  Please note that you can pick up race packets on the 26th of November between 3-5:00P at Woodstock Elementary School, 15 South St., Woodstock, VT 05091

  Registration on race day is at the...

  Hi Everyone,

  Please note that you can pick up race packets on the 26th of November between 3-5:00P at Woodstock Elementary School, 15 South St., Woodstock, VT 05091

  Registration on race day is at the Woodstock Elementary School. WE WILL HAVE LIVE MUSIC "JOHN SNYDER'S BAND!" BE SURE TO REGISTER BETWEEN 8:00 a.m. AND 9:30 a.m. SO THE RACE CAN BEGIN ON TIME!

  Thank you for registering for this enjoyable family event to support Zack's Place. On Thanksgiving Day, whether you are in Woodstock, the surrounding towns, Vermont, other states, or beyond, we are hoping to see your pictures or even see you in town walking or running the Zack's Place 5K Turkey Trot to support programs at Zack's Place.

  We have a couple of changes. Due to some canine issues last year, we are unable to host your dog or pets in this event. Please do not bring your pets to the Turkey Trot. Also, parking was somewhat difficult last year, and this year we will be providing you with parking suggestions below.

  The Zack's Place Turkey Trot, a 5K run and walk held on Thanksgiving Day, was established in 2007 and has become a dependable annual fundraiser ever since. In 2007, almost 200 people participated. In 2024, over 1,600 people participated and raised $119,000. All of the proceeds of the race are dedicated to our operational costs.

  In years past participants would line up and register for the race a band entertains them on a flatbed truck. Refreshments are offered. The race begins in front of the Woodstock Elementary School at 10:00 AM, with the more skilled runners in front and the rest following. The run meanders through the historic Village of Woodstock, then towards Billings Farm, around Mountain Avenue, and back around The Town Green, ending at the starting line. An award ceremony with refreshments and a band follows the race, where medals are presented.

  Families run together as college students and relatives gather for the Thanksgiving celebration. Grandparents and young children in carriages participate as walkers. It has become a tradition for many in the Woodstock area; however, we also have "satellite participants" who cannot be in Woodstock but run with family wherever they are: Hawaii, Italy, New York City, etc. This is indeed a day of thanks where individuals help support our enrichment center and simultaneously give thanks for their gifts.

  Suggested parking:

  1. Mill Building 21710- 41F Maxham Meadow Way Woodstock, VT 05091

  2. Sunset Farms 21710 Maxham Meadow Way, Woodstock, VT 05091

  3. East End Park 217-03 Maxham Meadow Way, Woodstock, VT 05091

  4. OHC/Masonic Temple 30 Pleasant Street, Woodstock, VT 05091

  5. Billings Farm and Museum 69 Old River Road, Woodstock, VT 05091

  6. Woodstock Rec. Ctr. 54 River Street, Woodstock, VT 05091

  7. Woodstock Country Club 78 South Street, Woodstock, VT 05091

  8. Village of Woodstock Street Parking: Elm Street, Central Street and Pleasant Streets only

  No parking around the Woodstock Village Green*

  3.1 Miles Run Walk

  Windsor County, Vermont, 05091, United States
  OpenStreetMap Google Maps