Events in Windsor County, Vermont | 2026-2027

Runamuck 50k [facebook.com] [Register at ultrasignup.com] - Facebook

Sat, Apr 11, 2026 at 8:00 AM

50k Run Ultra

247 Stage Rd, Windsor County, Vermont, 05067, United States
OpenStreetMap Google Maps

Divided Sky Fun(d) Run, 2026 [raceroster.com]

Sat, May 16, 2026 at 9:00 AM

Description

Divided Sky Fun(d) Run

Join us in beautiful Ludlow, VT for the 5th annual Divided Sky Fun(d) Run! Participate in this in-person or virtual 5K to support addiction recovery and build community with...

Divided Sky Fun(d) Run

Join us in beautiful Ludlow, VT for the 5th annual Divided Sky Fun(d) Run! Participate in this in-person or virtual 5K to support addiction recovery and build community with runners, walkers, and good people of all kinds.

Please note, this is a sober event and all proceeds benefit Vermont addiction recovery programs.

Once again, we have a registration discount available for local participants who reside in Windsor or Rutland County. Email dividedskyfunrun@gmail.com for additional information.

Jackson Gore is offering 20% discounted room rates. Call 855-945-0553 and use the code SOKDSF26 or make reservations here.

The Fun(d) Run is part of Divided Sky's BIG Weekend which includes the 3rd Annual Music on the Mountain. Get all the details and tickets at bigweekend.org.

We are still accepting sponsorships at this time. Please reach out for more information.

REGISTER BY MARCH 25th TO GUARENTEE SHIRT SIZE.

5k Run Virtual Walk

Jackson Gore Ice Skating Facility, 36 Jackson Gore Road, Windsor County, Vermont, 05149, United States
OpenStreetMap Google Maps

BarnArts Race Around the Lake [runsignup.com]

Sun, May 17, 2026 at 10:30 AM

Description

Race Around the Lake 2026

Sunday, May 17

Silver Lake State Park

Events

5K Run/Walk

10K Run

Early Registration Fees (through May 9)

5k Adults: $40

10k Adults: $50

12 & under: $25 (age-based pricing...

Race Around the Lake 2026

Sunday, May 17

Silver Lake State Park

Events

5K Run/Walk

10K Run

Early Registration Fees (through May 9)

5k Adults: $40

10k Adults: $50

12 & under: $25 (age-based pricing kicks in automatically!)

Race routes circle Silver Lake on town roads, dirt roads and single-track wooded trails with intermittent views of the lake.

Sign up by April 30 to receive our Race Around the Lake T-shirt with your registration!

10K Race begins at 10:30am
5K Race begins at 11am
Post-race activities include a Chef's Table lunch, awards and live music along the lakefront

Awards will be given to the top 3 finishers in each race, plus the top finishers in age categories.

Schedule of Events

9:00 – Registration/Check-in begins

10:30 – 10k Start

11:00 – 5k Start

11:30-12:30 – Post-Race Activities: Chef’s Table, Live Music

12 noon – Awards

Virtual 5k or 10k

Adults: $25

12 & under: $15 (age-based pricing kicks in automatically!)

Virtual participants: race on your own wherever and whenever you wish, and still support BarnArts and our youth programming! Share your photos with us! Sign-up by April 30 to get a race T-shirt!

Thank you for supporting BarnArts!

All funds raised directly support our Youth Programming and make this summer's Summer Youth Theater camp possible! Race funds allow us to provide scholarship support for all Summer Youth Families in need.

5k 10k Run Trail Virtual Walk

Windsor County, Vermont, 05031, United States
OpenStreetMap Google Maps

Ascutney Mountain Run [runsignup.com]

Sat, May 30, 2026 at 9:00 AM

Description

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]

Sun, Jun 07, 2026 at 6:00 AM

Description

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]

Sun, Jun 07, 2026 at 8:15 AM

Description

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]

Sat, Jun 27, 2026 at 8:30 AM

Description

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]

Sat, Jul 04, 2026 at 9:00 AM

Description

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

Fri, Jul 10, 2026

Run Trail

Windsor County, Vermont, United States
OpenStreetMap Google Maps

Vermont 100 Endurance Race [vermont100.com]

Fri, Jul 17, 2026

100k 100 Miles Run

411 Cemetery Road, Windsor County, Vermont, 05089, United States
OpenStreetMap Google Maps

Lover's Lane [facebook.com] [Register at ultrasignup.com] - Facebook

Sat, Aug 08, 2026 at 8:00 AM

Ultra

Chester Municipal Pool, Windsor County, Vermont, United States
OpenStreetMap Google Maps

Triquest Gravel Triathlon 2026 [runsignup.com]

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]

Sun, Sep 27, 2026 at 6:00 AM

Description

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]

Thu, Nov 26, 2026 at 10:00 AM

Description

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:

Mill Building 21710- 41F Maxham Meadow Way Woodstock, VT 05091
Sunset Farms 21710 Maxham Meadow Way, Woodstock, VT 05091
East End Park 217-03 Maxham Meadow Way, Woodstock, VT 05091
OHC/Masonic Temple 30 Pleasant Street, Woodstock, VT 05091
Billings Farm and Museum 69 Old River Road, Woodstock, VT 05091
Woodstock Rec. Ctr. 54 River Street, Woodstock, VT 05091
Woodstock Country Club 78 South Street, Woodstock, VT 05091
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

15 events in Windsor County, Vermont

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