8 Bike Rides of Your Life


The way up and the way down are not, just not, one and the same. 

That’s all I can think as I push/pull/cajole the wheels into one more rotation, then another. I stand, putting my full weight on the pedals. Think positive, I coach myself. I’m grateful .. grunt.. for the cool green tunnel of hardwoods shading the road. Grateful ..groan..for the­ packet of maple syrup from the last aid station, liquid energy. I’m grateful for the six guys who let me draft for the last 10 miles. Grateful for the swimming hole ahead that’s going to be deliciously cool.

Then, the trees open up. There is light. The road crests at the gap. Below, a toy landscape of farms with red barns spreads out. Patches of green fields are dotted with miniature black and white cows. A white spire rises through trees in the distance. I pause to take a swig of water, shift into my largest gear and then let go, screaming down the other side, taking the S turns like a ski racer on a GS course.

By far the best way to see Vermont, I’m convinced, is on a century ride or organized group ride. In the past few years, a host of new rides have sprung up with events such as the Vermont Challenge, Farm to Fork Fondo, and the Vermont Gran Fondo, making the national Top 10 lists. Others, like the Tour De Kingdom, are lesser-known gems that will show you roads you never knew existed.

Yes, you pay an entry fee but you get a sag wagon, in case you have a mechanical issue. And then there are the aid stations. Since this is Vermont, instead of GU and Budweiser, there might be PB&J sandwiches on slabs of homemade bread (Vermont Challenge) or woodfired pizza with farm-fresh toppings (Farm to Fork Fondo). After parties? In Vermont, you don’t bring the beer to the party, you take the party to the beer. Three rides start and finish at Harpoon Brewery, Long Trail Brewery and Woodchuck Hard Cider this year.

While there is an organized ride somewhere in the state nearly every week,  here are some of our favorite loops, in calendar order.


The Tour de Kingdom Burke to Quebec and back, June 9-22 and again, Sept. 22-24

You have two chances to ride on some of the least-traveled roads in the state as the Tour de Kingdom (three days of supported rides) takes place during both the dandelion season of spring (June 9-11) and the prime foliage of fall (Sept. 22-24). Both Tours take riders on the nearly-empty backroads through the wide open country of the Northeast Kingdom on routes that include Friday’s 65-mile tour around Lake Memphremagog and Sunday’s century ride from East Burke to the lake region, including passing Lakes Willoughby, Memphremagog, Seymour and Island Pond. The highlight of the three days is The Moose, a 107-mile ride (with timed sections you can race) that heads into the remote northeastern corner of the state before returning along newly-paved roads that border serene stretches of the Connecticut River. As organizer Phil White notes, “We call it the Moose because you are more likely to see moose on the route than cars.” Kingdomgames.co 


Long Trail Century Ride: Bridgewater to Ludlow and back, June 24

In winter, you might drive the section of Route 100 between Okemo and Killington without ever noticing the stretch of frozen lakes. Come summer, those lakes come alive and so do the backroads of central Vermont. Based out of the Long Trail Brewery in Bridgewater Corners, the Long Trail Century Ride offers several options including 100-, 60-, 40- and 20-mile loops and, new this year, a mountain bike session at Killington Resorts’ Snowshed trails.

It’s hard to say what’s better, the route (which goes past Killington and Pittsfield, up into the hill town of Barnard and back down toward Woodstock and Ludlow before returning on Route 100) or the after party at Long Trail (with beer, live music, a barbecue, face painting and kids games, vendor tents and corn hole by the river). But perhaps the best part of the ride is that it’s a fundraiser (with a minimum $100 threshold to register) for a good cause: Vermont Adaptive Ski & Sports. Longtrailcenturyride.com


Vermont Gran Fondo: Middlebury to Mad River Valley and back, July 1

Keep thinking about what’s waiting at the finish at Woochuck Cider’s tasting room, and it just might help you get over the steepest paved mile in America. Just south of Sugarbush, Lincoln Gap is closed in the winter when its steepest (24 percent) pitch makes for extreme sledding. Come summer, it’s one of those notch-in-the-belt rides that Vermonters pride themselves on accomplishing. Olympic mountain biker (and former Middlebury College ski racer) Lea Davison holds the QOM (Queen of the Mountain) title on Strava for ascending the 1.3-mile, 15-percent grade, 1,100 elevation gain section in 14 minutes. She’s also called the Gran Fondo the “toughest race” of her life. The Gran Fondo’s motto? “Ride it if you can.”

Lincoln is just one of four gaps and one of two Category 2 climbs that help you accumulate 10,495 feet of climbing over the course. The 2017 course has riders screaming down the paved Appalachian Gap, past Mad River Glen and views of Sugarbush before heading up Lincoln Gap and then back over App Gap. From there, you head south on Route 100 past waterfalls and farmland. The fourth and last gap, Middlebury Gap, descends past Middlebury Snow Bowl with views to the Adirondacks before ending back at Woodchuck Cider.

If you’re not up for that type of punishment, Medio and Piccolo Fondo routes let you drop a gap, or two, or three and still enjoy the scenery. There’s also the option to stop at three classic old-time Vermont general stores in Ripton, Warren and Northfield.  Vermontgranfondo.com


Gravel roads and covered bridgs are part of Raid Lamoille.

Raid Lamoille: Stowe to Craftsbury and back, July 8

“Gravel grinding,” riding the back roads far from traffic, has become a thing around Stowe. So has the Raid Lamoille. It started in 2012 as a group of friends riding together to discover some of the better dirt roads in the area. Five years later, it’s an official ride. The 100K and 50K routes are unsupported (meaning no rest stops or aid stations) but routed to take you by some of the region’s most beloved country stores, including the Craftsbury General Store. While it’s not a race, the “raid” lives up to the meaning of its French name: a long or challenging ride. Expect a fast-paced group and some 6,000 feet of vertical climbs. Race organizers recommend a gravel or cyclocross bike and 28 mm tires or larger. Perhaps the best news about this year’s event? The Alchemist brewery will be providing liquid refreshments at the finish. Raidlamoille.com 


Farm to Fork Fondo, Pittsfield to Woodstock and back, July 16

In Italy, a “fondo” means a non-competitive bike ride or tour. After 13 years as a competitive pro cyclist, Tyler Wren has brought the comforts a European bike vacation to a new series of fondos that combine his passion for farms, food and, of course, bike riding. Wren, a Princeton grad who now lives in Burlington, now hosts Farm to Fork Fondos  in the New York’s Hudson Valley and Finger Lakes regions, in Pennsylvania, Maine and the Berkshires.

This July’s Vermont event kicks off with a Meet the Farmers Dinner in the elegant barn at  Riverside Farm, the Pittsfield estate owned by Spartan Race founder Joe De Sena. It ends back there with a farm-to-table dinner of heirloom squash salad with Maplebrook feta, mint and chili and grilled Misty Knoll chicken salad. The catering is by Vermont Farms Catering’s Kevin Lasko, the acclaimed chef behind the Backroom in Pittsfield.

You’ll work up an appetite riding the 93-mile route to Woodstock, then north over Bethel Gap to finish cruising past the stunning farmland and quiet valley between Rochester and Pittsfield. Aid stations? They highlight offerings from local farms—try Sandy’s Bakery’s Flower Toast (yes, made with edible fresh flowers) or Raspberry Tarts or Maple Candies from North Hollow Farm. Farmtoforkfondo.com

Harpoon Point to Point: Windsor to Strafford and back, August 12

Though it is no longer a point-to-point ride, this ride covers a variety of terrain as it leaves the Harpoon Brewery in West Windsor and heads north along the Connecticut River. The 100-mile route will take you all the way to White River junction and into the quiet hill towns of Strafford and Topsham before heading south again to Barnard and Woodstock. Make no mistake: this is a hilly ride, but you’ll know you earned that cold one at the end. There are also options for 50- and 25-mile rides and a 20-mile mountain bike loop around the trails at Mount Ascutney. Put on by Harpoon and National Life, the ride is  one of the biggest fundraisers in the state for the Vermont Foodbank, raising more than $200,000 in 2016.  Harpoonpointtopoint.com

Heading out from Stratton on Day 3 of the Vermont Challenge. Photo by Hubert Schriebl

The Vermont Challenge: Stratton to Okemo and back, Aug. 17-20

If you took the best aspects of a multi-day guided bike tour (sag wagons, lunch stops, dinners sharing stories of the day over a craft brew) and combined it with four days of the semi-competitive (read: bragging rights only) fun of a century ride, you’d get the Vermont Challenge.

Stratton skier John Sohikian dreamed up the Vermont Challenge as way to showcase some of the best riding routes in southern Vemont. The four-day event heads along the valley between Manchester to Dorset, before climbing into the mountains around Stratton and sending riders on a 107-mile fondo toward Okemo.

Of course, you don’t have to do all four days of rides. You can sign up for shorter routes each day (starting at 23 miles). You can stop where you want (last year’s favorite rest stop was at Wilcox Dairy, which makes a killer salted caramel ice cream). You can join in the group kickoff dinners at the Taconic Hotel in Manchester or eat on your own. You can do just the Valley Days (Day 1-2) or just the Mountain Days (Day 3-4). In 2016, the fifth running of the Challenge the ride raised $9,200 for local charities and $10,000 the year before. vermontchallenge.com 


Kelly Brush Ride,  Middlebury to Charlotte and back, Sept. 9

The Kelly Brush Ride doesn’t go anywhere near a ski lift–most of its routes cross the rolling farmlands  and orchards of Addison County. But it probably attracts more top skiers per entrant than any other event—including, in past years, Mikaela Shiffrin, paralympic medalist Chris Waddell, and, of course, Kelly Brush. Brush, whose mother was an Olympic ski racer, was racing for Middlebury College when a crash on the mountain left her with a severe spinal cord injury. She and her now-husband Zeke went on to found the Kelly Brush Foundation to promote safety in ski racing and help others with spinal cord injuries pursue sports.

Ski race teams from schools and academies around New England show up to support the event, which means the pace at the head of the pack is smoking fast. But there are multiple options for start times and distances, ranging from 25 to 100 miles, and more than 800 riders of all abilities participate. The 100-mile route takes you past the shoreside farms near Lake Champlain, through the village of Vergennes and the covered bridges of Charlotte before heading back along hills of Addison County with western views of the farmland and the Adirondacks. Kellybrushride.com

Lisa Lynn

Editor of VT SKI + RIDE and Vermont Sports.