Vermont is well known for more than a few things. For example, its high-quality maple syrup, award-winning craft beer, more than 8,500 miles of rolling dirt roads, barns and covered bridges, the burgeoning dairy industry (think Cabot cheese), the von Trapp-inspired movie, The Sound of Music, and the senior U.S. Senator, Bernie Sanders. We can also add some fun, festive, and downright challenging trail, ultra, and backyard events to that list.
Since the winters in the Green Mountain State are extremely cold and snow-packed, Vermont really utilizes the time on trails from May through November to take advantage of the warmer weather. Here is a list of events during that precious time. And you can bet there will be plenty of historic covered bridges to cross and maple products to indulge in!
In addition to the events listed below, check out these additional Vermont races: Springfield Stars & Stripes 7.4K (July 4, Springfield, Vermont), Goshen Gallop (July 11, Goshen Vermont), The Magnificent Bastards Challenge (July 25, Corinth, Vermont), Lovers Lane (Aug. 8, Chester, Vermont), Westmore Mountain Challenge (Sept. 26, East Charleston, Vermont), Paine Mountain Trail Races (Sept. 27, Northfield, Vermont) and Mount Ascutney Vertical Backyard (Nov. 21, Brownsville, Vermont).
Looking for races in another state or region? Visit UltraSignup’s race finder.
Infinitus
May 21-30, Ripton, Vermont
888K, Deca-Marathon, 250 miles, Penta-Marathon, 88K, 100 miles, 26.2 miles, 9 miles
Race organizers keep upping the mileage ante with 100-mile races, 200-mile races, and now even 250- or 300-mile races. That’s when The Endurance Society, organizers of Infinitus, said, “hold my beer!” and dropped an 888K race. That’s 551 miles for those of you who don’t live near the Canadian border and don’t know how to convert metric distances.
Infinitus offers a welcoming, festival-like atmosphere and offers some very convenient amenities, such as camping for only $12, no matter how long you stay, 10 days of dorm lodging for only $150 available for participants and support crews, bathrooms and hot showers, a dining hall, and more. This sounds more like a lifestyle than a running race!
The course consists of two loops forming a figure-eight, sticking with the symbolism of the number 8 (when turned on its side it becomes the infinity symbol). Only six individuals have ever finished the 888K, giving it a lower finisher rate than the infamous Barkley Marathons. If you are not quite ready for a race that long, they offer shorter distances, like 250 miles. Who knew that all you needed was a 551-mile-race to make a 250-mile-race sound easier!
Organized by Endurance Society
Information and Registration: Infinitus
The Black Fly Trail Run
May 30, Westmore, Vermont
Half Marathon, 10 Mile, 5K
In keeping with traditional Vermont hospitality, this event welcomes people of all abilities to explore the beauty of North East Kingdom private and state land in the springtime. The 5K is a short jaunt on a mix of dirt roads and trails to circumnavigate Sentinel Rock State Park (600 feet of elevation gain) and finish with epic views. The 10 Mile is for those seeking a little more gain (1,200 feet), climbing Goodwin Mountain on ATV trails and singletrack trails.
The premiere event, the half marathon (13-ish miles), hits you with 3,300 feet of vertical gain on dirt roads and private trails, which will take you up and down two mountain summits. These courses are not PR courses, so be prepared to encounter some mud, mixed terrain, and proper climbing and descending.
The races are only a warm up for what’s to come once you cross the finish line. You will be treated to picturesque farmscape, which includes a North East Kingdom wedding venue, a “Vermont-style” meal with locally sourced farm-to-table ingredients, local vendors, refreshments from the local Red Barn Brewery or Athletic Brewing NA beer, and even a good ol’ barn dance party with live music from local band, Ashley Jane’s Hootenanny!
So lace up your trail shoes then pull on your boots for a fun-filled day on 1,000+ acres of private land. And why is it called The Black Fly Trail Run, you ask? It doesn’t matter, just be sure to wear bug repellent.
Organized by CrossCycle Fitness & Adventures
Information and Registration: The Black Fly Trail Run
Race to the Top of Bradford
June 6, Bradford, Vermont
5K, 1.5 miles
We all love the trails that we get to run and recreate on, that is why the Race to the Top of Bradford supports those who build and maintain those trails, with all proceeds of the event going back to the Friends of Wrights Mountain Fund. This race will take you on a 850-foot ascent and descent of Wright’s Mountain on the beautiful, single-track trails of Bradford’s town-owned forest. If you are wanting something a little more mellow, the 1.5 Mile fun run course stays on the lower wooded sections of the forest and is open to kids 13 and under and walkers. Don’t forget the post race refreshments and musical entertainment which you should come to expect from any Vermont trail race. And a special thanks to those who care for our trails!
Organized by Race Mozey
Information and Registration: Race to the Top of Bradford
SINduda
June 18, Rupert, Vermont
48 Hours
SINduda can be best defined as an “Adventure Race unlike anything you have ever experienced before.” It takes place in the mountains of Rupert, Vermont and it could take up to 48 hours to complete. There is no advertised distance or designated course, so be prepared for anything. And by anything I mean: hiking, rucking, running, swimming, escaping, locating water sources, wood carving, negotiations, physical calisthenics, briefings, bushwhacking, origami, exams, sensory deprivation, haiku, application and efficacy of advanced interrogation, saving the lives of countless people, and probably most importantly, pizza making. That is actually all in the race description!
So, if this is the type of race that appeals to you, be sure to show up with a strong body and mind…and perhaps some culinary skills.
Organized by Endurance Society
Information and Registration: SINduda
Catamount Ultra
June 20, Stowe, Vermont
25K, 50K
This race will take you into the scenery of The Sound of Music, as it is run on the grounds of the famous Trapp Family Lodge just outside of Stowe, VT. You’ll be able to feel the magic as you roll through the wide trails surrounded by highland pastures, grazing cattle, hardwood forests, and maple trees from where some of that delicious maple syrup comes from that you’ll probably be consuming after your race, or perhaps during the race if you use local Vermont race nutrition brand, UnTapped.
The 25K will circumnavigate the well-maintained trail system at the foot of Vermont’s highest peak, Mount Mansfield. The 50K course will complete the loop two times with an elevation gain and loss of about 5,000 feet. Local VT trail rippers, like Eric LiPuma and Mead Binhammer, have some of the fastest times ever run on the 50K course.
And the experience wouldn’t be complete without an award-winning Kölsch or Helles Lager from von Trapp Brewing located right on property.
Organized by Ironwood Adventure Works
Information and Registration: Catamount Ultra
The Aliza Lapierre Fan Club Trail Race
July 18, Richmond, Vermont
26K, 50K 2-Person Relay, 50K
Named for the prolific US ultrarunner and local Richmond resident, Aliza Lapierre, the event started in 2020 when a group of friends hiked and ran what has become the 50K course, plus an additional 20 miles along the Winooski River. Lapierre was supposed to join the group, but had to pull out at the last minute because of pet sitting duties. The group jokingly named the adventure, “Aliza Lapierre Fan Club 50” and created awards for themselves. What started as a joke, is now a full-fledged trail event!
The 50K course is made up of approximately 8 miles of road and 23 miles of rugged trails through the towns of Huntington, Starksboro, Hinesburg, and Richmond and accumulates over 5,000 feet of elevation gain. The more mellow 26K traverses approximately 4 miles of road and 13 miles of rugged trails with 2,500 feet of elevation gain. Or you can choose a partner and complete the 50K relay. And, yes, Aliza Lapierre will be there…unless she has a pet sitting gig that she forgot about.
Organized by Richmond Trail Running Club
Information and Registration: The Aliza Lapierre Fan Club Trail Race
Moosalamoo Ultra
Aug. 1, Goshen, Vermont
36 miles, 14 miles
This favorite amongst the local Vermont trail runners will challenge runners to an option of 14 miles (Heavy Half) or 36 miles (Ultra) and take you on long, demanding climbs where you might possibly experience black bear sightings and will definitely experience stinging nettle along the way. The rugged-but-beautiful trails of the Mossalamoo National Recreation Area are loaded with mountain singletrack trails which will take you to the top of Mount Mossalamoo and offer spectacular views of Lake Dunmore.
The 14-miler accumulates about 2,400 feet of elevation gain, while the 36-miler gains more than 5,000 feet, both starting at the picturesque Blueberry Hill Inn. This is a family and dog friendly race, so bring all members of your family, whether they have two or four legs.
Organized by Ironwood Adventure Works
Information and Registration: Moosalamoo Ultra
Mozo Double Up
Aug. 16, Stowe, Vermont
11 miles
If you think this ~11-miler will be a breeze, wait until you hear it will serve up about 5,000 feet of climbing and descending over that distance! Trail running experience is critical on this course–you are actually required to submit Strava proof–as you will encounter extremely technical terrain, including “no-fall zones” where, if you do fall, serious injury or death may result. This just means that extreme focus on your footing is critical, so for your own good leave your cell phones and ear buds at home.
This beast of a race starts at the Stowe Mountain Resort and essentially climbs up and over Vermont’s highest Peak, Mount Mansfield, then turns around and does it again, hence the “Double Up” along with the huge elevation gain in such a short distance. Local and international trail and ultrarunning legend, David Sinclair, holds the course record in just over 2 hours.
With the extreme nature of this race, however, you will also get to experience the delicate and fragile environment which you will be carefully clawing and climbing your way through. So delicate, in fact, that this race is held every two years in order to limit impact on said fragile and delicate ecosystem. You will also connect with the Long Trail, Vermont’s famous 272-mile footpath which is the oldest long-distance trail in the US. If you want to run a race, enter a trail race, if you want to experience a challenge, run the Mozo Double Up!
Organized by Ironwood Adventure Works
Information and Registration: Mozo Double Up
Devil’s Den Ultra
Oct. 10-11, Bradford, Vermont
30 hour, 12 hour, 10K
As the name implies, this devil of a race is a choose-your-poison (length) on some rugged Vermont trails. If you just want a mild day, you can opt for the 10K distance and then cheer on the more sinister participants in the 12-hour and the downright hellish participants in the 30-hour event. Some might call it purgatory, but it will be peak foliage season, so it will at least be beautiful!
This 10K loop course on Wright’s Mountain is a mix of easy and runnable to steep and rooty on both public and private land. You will be treated to steep climbs and fun, fast downhills as you navigate your way through wooded terrain. The top male and female finishers for each length will receive the coveted Devil’s Skull, 100 mile finishers will be awarded a devilish belt buckle, and all finishers of the 12-hour and 30-hour will be presented with a Devil Tarot card for your “tarot reading.” The highest mileage on the course was set in 2021 by local teacher, Lance Parker, and Mike Willey at 102.4 miles, and has been matched two more times in 2024 and 2025. The current highest mileage on the course by a female is Taylor Verville, with 89.6 Miles set in 2025.
Organized by Race Mozey
Information and Registration: Devil’s Den Ultra
von Trapp Mountain Marathon
Oct. 17, Stowe, Vermont
26.2 miles, 13.1 miles
There is something special about the fall in Vermont, when the leaves are turning vibrantly yellow, orange, and red, the crisp air fills your lungs, and the hills are alive with the sound of music (I was contractually obligated to make that reference by the von Trapps). The challenging half marathon and marathon distances will traverse the beauty which is the Trapp Family Lodge, on a majority of winding single track, with some rugged dirt and gravel road/trail sections, culminating in a scrambling climb to the summit of Round Top Mountain. The half marathon will climb and descend 1,900 feet of elevation while the marathon will double that.
Come and enjoy the fall beauty of the Green Mountains, hit the world class trails on the beautiful lands of the von Trapps, rub shoulders with local running legends, like Kasie Enman, the women’s course record-holder and the 2011 World Mountain Running champion, and then stay for the Oktoberfest festivities that will be in full swing.
Organized by Ironwood Adventure Works
Information and Registration: von Trapp Mountain Marathon
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1 comment
Todd
Thanks for this – I had not heard of some of these gems that I will likely try! Another very unique one to put on the radar is the Jay Peak Trail Running Festival. The 53K has 10,500′ (yes that’s not a typo, more than double the Catamount 50K!) of both ascent and descent and much of it is either ski slopes or the very technical VT Long Trail; with a very tight 11 1/2 hr cutoff. But more importantly it is a very inclusive family oriented event. Saturday has three 5Ks of increasing difficulty, (and you can do all 3), plus a kid’s run. Oh yeah, and there is a Yeti mascot and beer and pizza after. The 50K could be the hardest one around. Cheers