Events Calendar

Welcome to the VT Sports calendar of regional outdoor events.

If you would like to have your event featured in our print and online calendars Submit Here.

May
5
Sun
Middlebury Maple Run
May 5 2019 @ 9:00 am – May 5 2020 @ 1:00 pm
Middlebury Maple Run
USATF-certified half marathon and 2-person relay, and a 3-mile fun run. Beautiful, scenic routes with views of the Green Mountains and Adirondacks. 50/50 mix of paved and dirt roads for the half marathon, all paved for 3-mile fun run. Well organized, great t-shirts, live music on course from Middlebury College student bands, post-race pancake breakfast with Vermont maple syrup. New for 2019—prize money and age group awards for the fun run. One of New England’s “must do” races.
Apr
4
Sat
Berkshire Highlands Pentathlon @ Berkshire East Resort
Apr 4 @ 10:00 am – 3:00 pm
Berkshire Highlands Pentathlon @ Berkshire East Resort
The annual Berkshire Highlands Pentathlon features many of the best outdoor adventures in our area, and can be done solo or as a team. The five events – a 4.2 mile road/trail run, a 16 mile cycling leg, 2 mile kayak, a 2 mile obstacle run, a mile hike to the top of the mountain and a downhill ski to the finish – can only happen on the same day at the turn of the seasons. It may be a bit cold for road biking and kayaking and a bit warm for skiing, but where else can you do it all the same day?
Apr
18
Sat
Rollin Irish Half-marathon
Apr 18 @ 9:00 am – 12:00 am
Rollin Irish Half-marathon
A scenic half-marathon on the country roads of Essex Town.
Apr
26
Sun
Dream Big 5K: Run, Walk, Roll @ Essex Middle School
Apr 26 @ 10:00 am – 12:00 pm

A community 5K, 1K and Fun Run for folks of all ages and abilities.
The Dream Big 5K is a fundraiser to support EDD Adaptive Sports programs.
We welcome runners, walkers, wheelchairs, power mobility and handcycles.

All racers receive a medal for participating, a race t-shirt, swag bag, and
special recognition for top 3 finishers in each division.

Adult $25 * Student $10 * Fun Run is free.

Sleepy Hollow Mountain Race
Apr 26 @ 12:00 pm – 2:00 pm
Sleepy Hollow Mountain Race
This race is part of the USATF New England Mtn Running Series. It’s a challenging 10km mtn/trail race on a combination of wide mowed cross country ski trails and single track. We have fun prizes, burrito bar after the race, an awesome Vermont atmosphere and you will most definitely see a few Star Wars costumes out on course!
May
2
Sat
13th Annual Waterbury Gravel Grinder
May 2 @ 8:00 am – 8:00 pm
13th Annual Waterbury Gravel Grinder

The Traditional Grinder at 25 miles or the Big Grind at 50 miles with lots of climbing and lots of dirt winding through the hills of Waterbury and beyond.

This is our largest annual fundraiser. All proceeds from the event directly support trail building and maintenance in the Waterbury Area–Perry Hill, Little River State Park, and elsewhere. They also help fund our long-range plans to link WATA trails to other local trail systems. So, come on out for a great day of riding!

May
3
Sun
Run/Walk for Jim 5K and Kids Races @ Collins Perley Sports Complex
May 3 @ 8:30 am – 11:00 am
Win an apple pie! 5K race is run on paved loop. First mile fast. Second mile a gradual uphill and finishes fast. Apple pies for age group winners! Walkers start at same time/ same route. The Kid’s Races varied according to age and start at 8:30am at the track with the 5k race/walk starting at 9:30am.
Middlebury Maple Run
May 3 @ 9:00 am – 12:00 pm
Middlebury Maple Run
USATF-certified half marathon and 2-person relay, and a 3-mile fun run. Beautiful, scenic routes with views of the Green Mountains and Adirondacks. A mix of trail, paved and dirt roads for the half marathon, all paved for 3-mile fun run. Well organized, great t-shirts, live music on course, post-race pancake breakfast with Vermont maple syrup, maple syrup nips for all finishers. One of New England’s “must do” races.
May
10
Sun
Persist 5K
May 10 @ 8:30 am – 11:00 am
Beautiful 5K walk/run along the banks of lake Champlain to support the Vermont Women’s Fund.
May
16
Sat
PUMP IT UP 5-MILER @ Jericho Elementary School
May 16 @ 9:00 am – 10:30 am
PUMP IT UP 5-MILER @ Jericho Elementary School
A perfect marathon tune-up! The Pump it up 5-miler is an out-and-back race on Jericho’s Old Pump Road, which is all smooth dirt and rolling hills. Post-race refreshments and prizes to top runners in each age group.
Grafton Bike & Brew Festival @ Grafton Trails & Outdoor Center
May 16 @ 11:00 am – 6:00 pm
Grafton Bike & Brew Festival @ Grafton Trails & Outdoor Center
The Grafton Bike & Brew Festival will be bustling with local food & craft beer options, not to mention a variety of bike demos available on site and vendor booths too. Trails will be open…so come and enjoy some of the earliest riding in Vermont! Enjoy live music all day and bring the kids to take advantage of youth specific events & clinics.
May
17
Sun
Vermont Sun Half Marathon, 5K & 10K
May 17 @ 9:00 am – 3:00 pm

5k, 10k, & Half-Marathon
Lake Dunmore, Vermont
Nestled against the Green Mountains, just below Rattlesnake Point is Branbury State Park. The lake region is a most spectacular and pristine place to run. Novice and advanced athletes alike marvel the beauty of our courses and enjoy the mountains, lakes and streams of Central Vermont.