Vermont’s Best Events — Black Diamond Awards

Our voters decided the year’s best events in the 2018 Black Diamond Awards. Here’s what you shouldn’t miss next year. 


Can 34,000 people be wrong? If anyone wondered if Killington could outdo itself in its second year of hosting the best women ski racers in the world, the Beast World Cup answered that. With a course that competitors described as “perfect,” parades of ski clubs from around New England, a free concert by Dispatch and an on-mountain village of vendor booths, the Killington “Beast” World Cup has become the kick-off party for the ski season. 1. Killington World Cup 2. Pond Skimming 3. Tailgating


Since its first running in 1981, the competition at the Craftsbury Marathon has grown  bigger and better. This past January, the event dovetailed with the U.S. Super Tour, bringing some of the continent’s top racers to compete in sprints while others went for the “Marathon’s” longer distances, 48K, 33K and 16K. To give a sense of who’s racing: local champ Hannah Dreissigacker, a 2014 Olympic biathlete won the women’s 48K. Hannah’s sister Emily competed in PyeongChang and their parents, both Olympic rowers, own the Craftsbury Outdoor Center.

But the race also attracts recreational skiers who come for the chance to pole up the rolling hills and fly down forest trails. Runners-up included the Stowe Derby,   (cancelled this year, for the third year running due to weather) and a new contender: the Camel’s Hump Challenge, which sends skiers on a 13-mile backcountry loop to benefit The Alzheimers’ Association. 1. Craftsbury Marathon 2. Stowe Derby 3. Camel’s Hump Challenge.


In terms of sheer numbers, the Vermont City Marathon is a perennial winner in this category. The largest running race in the state, it attracts nearly 3,000 runners to the streets and hills of Burlington, before finishing along the waterfront bike path with views of Lake Champlain and the Adirondacks. What many say is the best part of the race? The pre-race training runs, options to do a relay, taiko drummers, and the crowds that line Church Street. This year, the 30th anniversary, there’s an added bonus in the form of Meb Kelfizighi, an Olympic medalist, 2014 Boston Marathon champion and 2009 New York Marathon winner. But before you despair of winning this year, know this: he’ll only be running as part of a relay, along with four runners selected for their inspirational stories.

Also scoring with our readers is the Race to the Top of Vermont, a running and mountain biking race (choose, or do both) up Mt. Mansfield’s Toll Road, and the Middlebury Maple Run Sweetest Half,a 13.1 K which features pancakes and maple syrup for finishers. 1. Vermont City Marathon 2. Race to the Top of Vermont 3. Middlebury Maple Run Sweetest Half.

The Kelly Brush Ride, named best road cycling event for our 2018 Black Diamond Awards


In just 13 years, the Kelly Brush Ride has grown from a ride that gathered a few hundred Middlebury college students, alumns and ski racers into the most popular ride in the state, with more than 800 riders raising more than $500,000 to benefit those with spinal cord injuries and ski racing safety. The ride starts and finishes at Middlebury College, where Kelly Brush was on the ski team before a fall left her with a spinal cord injury.

Both Kelly Brush Davisson and Chris Waddell, a former extreme skier, are regulars in the hand bike division and ski teams from around the state come to ride the rural farmland roads that snake through Addison County. It’s not a race but with talent like this, it can feel like it.

Runner-up is the Long Trail Century Ride, based at Long Trail’s riverside brewery in Bridgewater, followed by the Harpoon Point to Point ride, this year starting at Ascutney Trails and passing through the hills and backroads of the Connecticut River valley. If you think cycling and beer go hand and hand, you’re right. 1. Kelly Brush Ride 2. Long Trail Century Ride 3. Harpoon Point to Point.



It’s hard to say which is more fun — the New England Mountain Bike Festival (NMBAFest) held each year at Kingdom Trails or the Vermont Mountain Biking Association Festival (VMBAFest) which has moved between Ascutney and Sugarbush in recent years and is back in Ascutney this year. Our readers rated them both tops in the state and with group rides, camping, bonfire, demos, a tent village of sponsors and product and, of course, mountain bike “Olympics,” they are just hands-down good times. And because of the timing, NMBA is June 22-24 and VMBA on July 27-29. There are good reasons to do both. For those who prefer a bit more suffering, the Vermont 50 came in second followed by Circumburke–both point-to-point challenging distance rides on a combination of trails. 1 (tie) NMBAFest and VMBAFest 2. Vermont 50 3. Circumburke.


With gravel grinding growing (say that three times fast), we have a new category this year. Rasputitsa, the spring suffer-fest that takes riders on the dirt roads (and sometimes snow-covered dirt roads) of the Northeast Kingdom in chilly April (April 21, this year) has been the undeniable king of these events. “It’s not about racing, it’s about challenging the human spirit,” the website states. That challenge often involves mud, sleet and even snow so thick you have to hike your bike for miles through it. And then there’s Cyberia, a 1.5-mile stretch of rutted hilly road that often has even top cyclists, such as Tim Johnson or Ansel Dickie, crying for mercy. In four years, race founders Heidi Myers (of Louis Garneau) and Anthony Moccia have grown this to attract nearly 750 riders in 2017 and the event often closes out. It’s also spawned others, such as the Waterbury Area Trail Alliance Gravel Ride and the Overland Grand Prix, which has even drawn mountain bike legend Ned Overend from Colorado to compete. 1. Rasputitsa 2. WATA Gravel Ride 3. Overland Grand Prix.


Once again, readers voted Joe De Sena’s Spartan Race, held in Killington each year, the toughest event in Vermont. The Ultra division sends teams and individuals out on a 30-mile course, attacking more than 60 obstacles with a winning finishing time of seven hours. Those “obstacles” can include anything from hauling a bucket of gravel up the mountain to shimmying up a rope, in the mud, to hitting a target with a bow and arrow. The mother of all obstacle races, Spartan has become a worldwide phenomenon. Runners-up  are the Race to the Top of Vermont (the race up Mt. Mansfield) and the Vermont 100, an ultramarathon held in West Windsor that is one of the four events in the Grand Slam of ultra-running. 1. Spartan Ultra 2. Race to the Top of Vermont 3. Vermont 100.


We love this category because we learn about  events like the Sleepy Hollow Funny Twunny, a 20-mile-ish race where you can deduct time by telling a funny joke. The Twunny didn’t win this year but perennial favorites did: Pond skimming, the annual Santa Run (how can hundreds of runners dressed as Santa Claus not be fun?) and the Polar Plunge to benefit Special Olympics Vermont.  1. Pond skimming 2. Santa Claus Race 3. Polar Plunge

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