10 Amazing Rides Around Vermont

Sick of riding the same loops over and over? Ready to get out of town? Here: our picks for the best road rides around the state.  

We have a challenge for you: Get off your beaten track and do an organized ride (a century, a 60-mile metric century or  shorter options) in every corner of the state. Sure, you could look at Strava or a map and figure routes out on your own, but organized rides make it easy with maps, signs, aid stations and post-ride parties. This year, there are a few new ones worth checking into.

Let us know how you’re doing on our social media (#VTCenturyChallenge), and what centuries and parts of the state we should add to the list. For details, see Calendar, p. 31.


With few hills, quiet farmland, vineyards where you can taste local wine and loads of places to cool off in Lake Champlain, cycling through the Champlain Island farmlands and villages should be on everyone’s bucket list. The century we love there is the Farm to Fork Fondo (July 20-21) which has options from 29 to 93 miles, gourmet “aid” stations at local farms and a catered barbecue—all celebrating what’s grown in the region.


Imagine riding for an hour through forests and high meadows on a perfectly paved road without seeing a car. You can do that in the Northeast Kingdom and joining The Tour de Kingdom (June 7-9) is one of the best ways to learn the routes. The tour is a weekend of organized rides that starts in Newport on Friday, moves to Burke Mountain on Saturday and loops up through the far northeast corner of the state. Then on Sunday the ride heads down past iconic lakes such as the dramatic Lake Willoughby.


Though its name makes it sound flat, riding in the Connecticut River Valley is anything but that: think short steep climbs to incredible views of farms and villages and steep descents past rushing valley streams. The reward, though, is seeing a part of Vermont that many people don’t. The Prouty (July 10) has introduced a Vermont gravel ride, a metric century that loops south from Hanover through some of Vermont’s prettiest small towns: Woodstock, Barnard, Tunbridge, Vershire and West Fairlee, to name a few.  Or, try the VSECU Point to Point (Aug. 10), which loops north from its start at Mt. Ascutney to Royalton before heading south again through Woodstock and Cavendish.


One of the larger rides in the state, the Kelly Brush Ride (Sept. 7) is also one of the most scenic and, like many, raises money for a good cause—helping those who have suffered from spinal cord injuries get back in action. From downtown Middlebury, the ride cuts west through the farmlands that border Lake Champlain, up to Charlotte and Shelburne and then back south, with hilltop views that stretch to the Adirondacks.


New this year, former pro cyclist Ted King and his equally strong riding partner and wife Laura King are hosting Rooted Vermont, Return to Gravel. Starting in Richmond, the challenging ride goes south on dirt roads, with some Class IV roads and “Vermont pave” to Ripton before returning north. The ride starts and ends at Cochran’s Ski Area and a portion of the proceeds will go to helping the ski area build mountain bike trails.

A bucket-list ride for anyone is the Lincoln-Appalachian-Middlebury-Branbury four-gap LAMB ride and the Vermont Gran Fondo (June 29) is a chance to do all those gaps with a crowd to support you. This year the ride starts in Bristol and has prizes for the man (KOM) and woman (QOM) who post the fasted times up Lincoln Gap – a 24-percent grade that’s been called the steepest paved mile in America.

If flatter terrain is more your speed, consider this: the Long Trail Century Ride (June 22) to benefit Vermont Adaptive starts and ends at the Long Trail Brewery in Bridgewater. Routes look mainly through the valleys of the central greens, with a few tough climbs in Barnard but a rewarding final stretch past the lakes that line Route 100.


If you think of Strolling of the Heifers as just a parade of cows through downtown Brattleboro, think again. Yes, it’s a weekend of festivals and cook-offs celebrating farms and local foods. But there’s also the Tour de Heifer, a 15-, 30- or 60-mile gravel ride. This year there’s an entirely new 60-mile route with 7,119 feet of climbing, almost all on dirt roads. The reward: a lunch of quiches and frittatas by Vermont Farm Table catering, fresh-baked cookies and local brews from Whetstone. Nearby, West Hill shop is offering $10 gravel bike rentals for the event.

On the other side of the state, the Tour de Slate held its inaugural event last year (and raised more than $17,000 for Teen Challenge, a drug and alcohol abuse recovery program). This Aug. 3, the event rolls through the quiet scenic roads of Slate Valley, that run along the southwestern side of the state, starting in Middletown Springs. In addition to the metric century, 36- and 24-mile routes there’s an 8-mile out-and-back on the restored Delaware and Hudson Rail Trail.

Featured Photo Caption: The Farm to Fork Fondo is a moveable feast through the flat farmland and vineyards of the Champlain Islands  Photo courtesy  Farm to Fork Fondo

Leave a comment