Pro Picks: Vermont’s 12 Best Gravel Rides  

With swimming holes to stop at, blueberries to pick, and bakeries and brewpubs to sample, these backyard loops—as picked by gravel pros— are the best ways to see Vermont.

Sure, you might think you know Vermont’s gravel. Perhaps you’ve ridden some of the better-known organized rides. But how much have you really explored the state? We asked gravel cycling experts around the Green Mountains, south to north, to share their favorite recreational (read: accessible) gravel rides in 20- to 40-mile loops.

The result are some stunning rides where you can camp out on the shores of Lake Champlain, pick blueberries, plunge into a river from a rope swing, cast a fly-rod, ride a rail trail, swim in the lake where Jacques Cousteau did his first dives, visit Robert Frost’s grave and treat yourself to sweeping views of the rural Vermont that pavement seems to have missed.

Download the map links, pack your saddlebag and plan your staycation.

 

1. BENNINGTON: HOLSTEINS, HISTORY AND ROBERT FROST — by Joe Cruz

The pro: Few people know bikepacking like Joe Cruz. Cruz, who commutes from his home in Pownal by bike to Williams College just across the Massachusetts border to teach philosophy is one of the most knowledgeable bikepackers in the country and a contributor to bikepacking.com. He’s the mastermind who mapped Ted King’s epic VTXL gravel ride from one corner of Vermont to the next. He’s also a less concerned with speed than with scenery.

The ride: This loop is everything Vermont: wooded corridors of green that turn incredible colors in autumn, working farms with Holsteins and soaring silos, rolling open valleys, and narrow roads lined by stone walls running alongside burbling brooks. It’s all easily rideable—no Class 4 sections on this one—but be ready for lots of Vermont- style climbing! Park at the Bennington Monument commemorating the pivotal Revolutionary War battle of 1777. From there, it is not long to the first gravel sections and a beautiful ascent along the shoulder of Mt. Anthony.

Once over the pass, hold on for a grinning descent into the town of Pownal where you’ll link up to a fast section of Route 346 before tackling the second major climb of the day on Ladd Brook Road. At the top of Ladd Brook, you’ll be on a pleasant network of woodsy rural roads with signs of sugaring operations and the occasional small farm.

The landscape opens up again on the rolling dirt of Middle Pownal Road on the way back to Bennington. The route finishes on quieter Bennington side streets but it is easy to detour a block or two north to the main commercial thoroughfare for a bite to eat or a pint. There’s one last modest climb before you arrive back at the Monument. Poetry buffs should set aside time to take a short well-signed walk through the cemetery at the Old First Church (mile 23.3) to visit Robert Frost’s grave.

The swimming hole: At mile 5.4, instead of turning left as the route indicates, go straight to stay on Fowler’s Way approximately .3 miles. There’s a small parking area on the left and a path into the woods. Follow it for a few minutes for a cooling dip.

The bike shop: Pop over the Mass. border to The Spoke in Williamstown where Heidi, Paul and Damien can fix anything.

The brew pub: The Madison Brewing Co. (at mile 22.1 stay on Route 7 to the intersection with Route 9 less than .1 mile, turn right, Madison on left).

Refuel here: Pizza at Ramunto’s in Bennington.

Map it: strava.com/routes/2717771383132915372 

2. SLATE VALLEY: RAIL TRAILS AND PAVE — by Caitrin Maloney & Hardy Avery

The pros: Caitrin, 43, and Hardy, 45, are the duo behind Sustainable Trailworks, the company that has built many of the now-classic mountain bike trails around Vermont. They recently moved from Lamoille County to a farm near Poultney, in southwestern Vermont, where they have been helping Slate Valley Trails create and map mountain bike and gravel trails. Caitrin and Hardy were among the top male and female finishers in last fall’s Gorey Hollows Race hosted by Analog Cycles. The race featured a brutal 80- mile, 13,000-feet of vertical, course.

The ride: This 29-mile “Adventure” gravel ride has a little bit of everything: quiet gravel roads, lots of hills, a couple of rough and tumble Class 4 “pavé” sections, expansive views (including of distinctive Bird Mountain), and a nice mellow cruise home on the D&H rail trail. This ride follows Ames Hollow Road through the Bird Mountain Wildlife Management area, which adds challenge and an awesome sense of adventure to the ride.

Got fatter tires? This would be a good time to use ‘em! The ride begins and ends in the historic Poultney downtown. Make sure to stop at Tap’s Tavern after the ride for great local fare and craft bevies.

The swimming hole: Look for dirt pull-off on the side of the road on Route 140 east of Poultney – there are numerous great spots to take a refreshing dip in the Poultney river. Or stop at Lake St. Catherine State Park, just south of town on Route 30.

The bike shop: Analog Cycles is a must. This unique, off-the-grid shop is located in an old sugarhouse at 181 Hillside Drive in East Poultney. Analog specializes in rad custom gravel bikes, custom bike fitting and also offers a range of cool bike bags and accessories.

The brew pub: Taps Tavern has an awesome local burger and craft beer selection. And your meal will be served on pottery that’s handmade by a local artist.

Refuel here: Stop by the East Poultney General Store for snacks on your way to a swim off Route 140. This quintessential general store is stocked with the expected and the unexpected, and in the summer months features a farm stand out front.

Map it: : https://www.strava.com/routes/2721441721310103728 

3. WOODSTOCK: ROPE SWINGS AND COVERED BRIDGES — by Ansel Dickey

The pro: Ansel Dickey, 25, has been racking up podium finishes since he was a junior racer at Killington Mountain School and did his first pro season as a Cat 1 racer in 2013. Now the owner of Vermont Social, he’s followed Ted King and many of the other top gravel riders as a photographer and videographer.

The ride: It’s crazy that riding “this good” exists for most Vermonters right out their back door. I love this route because I step out my door in Woodstock and in under 40 miles, I’ll pass through four village centers, go by four Vermont general stores, go through a covered bridge, pass a rope swing, and almost never touch pavement.

The swimming hole: On Old River Road in Taftsville/Woodstock you’ll find the rope swing that launches you into the Ottaquechee. It’s not the biggest rope swing, and it can be a tad shallow, but it’s great on a hot day if there’s not too many people about.

The bike shop: Drummond Cycles, of course.

The brewpub: Stop at the Brownsville Butcher and Pantry for a to-die for fried chicken sandwich, great local beer on tap from Trout River, Harpoon, Long Trail and many other nearby breweries.

Refuel here: The South Woodstock General Store and Mon Vert Cafe in Woodstock are two of my favorites!

Map it: https://www.strava.com/routes/2719207236671176494

4. RANDOLPH: BRAINTREE’S 5 CLIMBS — by Zac Freeman

The pro: Zac Freeman and Angus McCusker have been the force behind the Rochester/Randolph Sports Trails Alliance. The duo have helped to cut and map backcountry ski trails in Brandon Gap and are about to release a map of gravel rides in the Rochester/ Randolph area. Many routes start from The Hub, which features maps and trail information and is housed in the same building as Randolph’s new Gear House.

The ride: The Braintree 5 is an unforgettable 35-mile ride with 5,000 feet of climbing on some of central Vermont’s finest dirt roads. This ridge line route has you zigzag picturesque Braintree Hill with views reaching New Hampshire’s White Mountains. You can rest at the historic Braintree Meeting House, dunk your head in Thresher Brook and take in the beauty of rural Vermont. If you ride it in peak foliage it’s breathtaking. Start and finish at The Gear House.

The swimming hole: Plunge into the river under the footbridge at the Randolph Rec field.

The bike shop: The Gear House in downtown Randolph and RASTA Trail Hub.

The brewpub: Bent Hill Brewery (you pass it on the ride.)

Refuel here: There’s nothing on the ride, but The Black Krim Tavern in Randolph is a must.

Map it: strava.com/routes/10660797

5. NORWICH: HILLS AND HIDDEN HAMLETS – by Daniel Jordan

The pro: One of the founders of Vermont Bikepackers and the leader behind this year’s Super 8 Grand Depart, Daniel Jordan, 32, has ridden many of Vermont’s quite backroads and in 2015 did the VT50 (mountain bike race) on a road bike. Now based in Burlington, he recalls his favorite routes from his time spent working in Norwich.

The ride: I used to work at a small bike shop in Norwich, and this became a favorite route of mine. It’s only 21 miles, but don’t be fooled; there is 2,700 ft elevation gain and some very rugged terrain along Class 4 town highways.

The route starts with smooth dirt on the local classics: Bragg Hill, Chapel Hill, and Tigertown. Then suddenly, you take a sharp left to climb Sue Spalding Road. The road surface becomes rugged as you access the deep woods. You may have to walk, but don’t worry, the climb doesn’t last for long. As you start to descend, there are a few trails in there, so make sure you are trending to the south and west and you’ll be fine.

As you descend wild and woolly Po Dunk Road.=, keep your eye out for the Appalachian Trail as you should cross over it twice. After the long descents, you’ll climb up pavement to the Jericho Rural Historic District, a hidden hamlet with beautiful rolling farmland. The road turns to gravel near the top, and then it’s all downhill back to Norwich.

The bike shop: Cowbell Mobile Bike Shop is based in the area. Mason Racing in Lebanon is great, and the legendary Drummond Cycles is also nearby.

The brewpub: Right in Norwich, get a beer at the Brewery at the Norwich Inn, home of Jasper Murdock Ales. Their highlight is English style cask ales.

Refuel here: The route takes you up into the hills where there’s not much in the way of stops. Before you set out, you can load up on snacks and sandwiches at Dan & Whit’s in Norwich, or you could start with a coffee and pastry fuel-up at King Arthur Flour.

Map it: ridewithgps.com/routes/33555875

6. TUNBRIDGE: BIG VIEWS & SWIMMING HOLES — Alex Buskey

The pro: Alex Buskey, 29, founded The Ranger gravel ride as an innovative approach to land conservation, social equity, and sustainability. He’s ridden in nearly every corner of Vermont but calls Tunbridge home, in part for rides like this.

The ride: One of my all-time favorites ride is, of course, in Tunbridge. Swing in to First Branch Coffee for a pre-ride buzz and tasty treat before departing SoRo (South Royalton). I prefer to ride this route at a cruise pace to make it an all-day ride. I might even pack a collapsible fly rod to take a few casts in the First Branch of the White River below the Larkin Road Bridge while I dry off from a quick mid-ride swim.

You really feel like you are out there when you reach Quarry Road. There’s a beautiful pond with a lookout to your left as the road begins to flatten out. At this point you’ll be ready for that mid-ride swim. Look back behind you at the view over the Tunbridge Hill Organic Farm as you begin to reach the high point of Monarch Hill Road. Cruise along Kelsey Mountain Road with views to the west of Randolph.

It’s not called Kelsey Mountain for nothing. There’s a kicker of a climb hidden at the end of this one. Descend back down into the valley via Falls Hill Road onto one of Tunbridge’s most photographed riding spots, Howe Lane. Get a photo of the famous Howe Farm. If you head north (left) on Route 110 towards the Tunbridge Fairgrounds, there are a couple of good swimming holes along this section of the First Branch up until the Cilley Bridge. You’ll then spin back to town along Route 110. There is one more swim spot along the White River after you cross the bridge on your right, before the Vermont Law School and SoRo village. You’ll see a small parking lot close to the water with a beach and some ledge. You’ll likely be ready for some food by now. I’d recommend the Worthy Burger or First Branch/Upper Pass Beer Co.

The swimming hole: The hole below the Larkin Bridge in Tunbridge is the perfect cool down spot.

The bike shop: There isn’t a bike shop in South Royalton yet, but the Gear House in Randolph, and Green Mountain Bikes in Rochester are both trusty shops with unique atmospheres.

The brewpub: Upper Pass Beer Company and Worthy Burger are both great spots in South Royalton. The Upper Pass tasting room is located in First Branch Coffee.

Refuel here: The nice thing about this loop is that once you are out there, there’s really not much around you. Grab to-go snacks at the SoRo Coop before heading out (don’t forget to bring your reusable containers or wraps).

Map it: strava.com/ routes/2718328803651856044

7. BUTTON BAY: BOVINES & BATTLE GROUNDS /ADDISON COUNTY — Kris Dennan

The pro: As the owner and leader of the touring company, Gravel Tours, Kris Dennan, 46, has explored most of Vermont by bike, including doing the 300-mile VTXL (see story on page 8) in 23 hours of saddle time. Though he’s based in Manchester, one of his favorite rides is along the shores of Lake Champlain near where his grandfather had a camp.

The ride: Start at Button Bay State Park (camp out the night before if you can) and roll south along Lake Champlain on quiet farm roads, with views of the Green Mountains to the east and west to the High Peaks of the Adirondacks. You’ll pass by working dairy farms on roads built by the British military that connected old Fort No. 4 in Charleston, N.H. to Fort Ticonderoga and Fort Henry in New York during the battles for Independence in the 1700s.

Ride across the Crown Point Bridge and tour Fort Henry and swim in the lake. The terrain is rolling with some short, punchy climbs and offers up a nice mix of gravel and quiet, paved farm roads

Crossing Route 7 you’ll climb slightly, just to the base of Snake Mountain and head north, passing the hiking trailhead to the summit where a resort once stood upon the cliffs, overlooking the lake. The roads leading into Vergennes are a bit more undulating, building your appetite for some good local food and drink, of which there are plenty of choices in town.

The swimming hole: You’ll have plenty of options as you ride along Lake Champlain.

The bike shop: Frog Hollow in Middlebury.

The brewpub: Hired Hand in Vergennes.

Refuel here: The Bridge Restaurant at the Crown Point Bridge.

8. RICHMOND: BLUEBERRY PICKING AND GORGES — Chelsea Camarata

The pro: It doesn’t take much to get Chelsea Camarata out riding dirt or gravel. As the founder of Kaden Apparel, the mountain bike apparel company for women, Chelsea is constantly out testing product, often with her partner, photographer Ryan Bent.

The ride: This 19(ish) mile loop starts at the Round Church in Richmond and goes along the Cross VT Trail toward Huntington and finally loops back to Richmond with an incredible downhill that will make all the climbing worth it.

You will find yourself surrounded by beautiful farm fields, some classic Vermont barns, and quiet dirt roads. We think this is a perfect climbing to downhill ratio for anyone looking for a quick before/after work ride or just getting into riding gravel. Spin it quickly or take your time and stop at Owl Head Farm for pick-your-own blueberries, have a picnic at Gillett Pond, or ride the River Trail by Cochran’s Ski Area. Feeling like a longer route? Try riding from Burlington via Governor Chittenden Roadfor a total of 45 miles.

The swimming hole: Huntington Gorge, Bolton Potholes or Winooski River.

The bike shop: Hitchhiker Mobile Bike Shop – They’ll come to you!

The brewpub: Stone Corral Brewery in Richmond

Refuel here: Stop at Sweet Simone’s in Richmond for granola bars for on the go, coffee cake to die for and breakfast sandwiches made with buttermilk biscuits, a fried egg, and Cabot cheddar.

Map it: 19 mile: strava.app.link/ qimnhutX77

45 mile: strava. app.link/89lwN8BX77

9. STOWE: SWEET GRAVEL & GREAT BREWS – Ted and Laura King

The pros: As if being the two-time winner of Dirty Kanza and podium finisher at a host of other gravel races didn’t earn him the title of Gravel King, Ted and his equally speedy gravel-riding wife Laura founded Rooted Vermont, now a gravel classic as well, when they moved to Richmond two years ago. A Middlebury grad, King has been riding Vermont’s dirt roads for decades.

The ride: It’s not my backyard, but it’s worth the trip to Stowe to make it happen. The Saturday morning ‘Stowe Gravel Worlds’ route is a weekly group ride from late spring through early fall that features mostly buff, sweet gravel roads for which Vermont is well known, but still a few brief Class 4 sections to keep you on your toes, plus plenty of room for detours and derivations from the route to really mix it up.

Hilly to keep you honest, but short enough to be home by late morning. You’ll already be buzzing when you wrap up the ride, but this route finishes at PK Coffee to continue that morning buzz.

The swimming hole: If you’re baking hot, you could take a dip in the West Branch.

The bike shop: Ranch Camp has you covered.

The brewpub: The Alchemist is almost too easy an answer. Idletyme is across the street from PK Coffee.

Refuel here: Start (or finish) with a strong brew and pastry at PK Coffee. Ranch Camp will help replenish what you’ve lost along the way when your morning coffee and pastry have worn off.

Map it: strava. com/routes/29080003

10. PEACHAM: DAIRY FARMS AND CREEMEES — By Ian Boswell

The pro: One of the reasons former Tour de France pro rider Ian Boswell, 29, moved from Nice, France to Peacham, Vermont was for the vast network of quiet back roads he could train on. While the Peacham Fall Fondo (the gravel grinder he and his wife Gretchen began putting on two years ago) has been canceled for 2020, you can still ride some of their favorite gravel routes.

The ride: This is a quintessential 29- mile route starting and ending in the center of Peacham at the Peacham Cafe. You will take in the rolling hills of the Northeast Kingdom (gorgeous in any season!) and have sweeping views of the White Mountains. You will pass active dairy farms including the Kempton Farm, which produces the milk for my favorite cheese: Cabot Clothbound Cheddar by Jasper Hill Farm. While this is a beautiful loop, it is challenging, with over 4,000 feet of climbing in just under 30 miles.

The swimming hole: After your ride and a maple creemee at West Barnet Quick Stop, jump in Harvey’s Lake — the site of Jacques Cousteau’s first dive while he was at camp near there as a boy — at the free public beach.

The bike shops: Bring your tools! The closest bike shops would be Village Sport Shop in Lyndonville or Onion River Outdoors in Montpelier.

The brewpub: Red Barn Brewing just expanded to open up a sweet new location in Danville; beer of choice: Little Devil.

Refuel here: The community-owned Peacham Cafe is a great spot for a bite before or after the ride, and you should pick up some amazing Artesano ice cream in the freezer there. There are many other local products for sale, and Crystal and Shannon are always cooking up fresh pastries. Check out the “most photographed church in Vermont” at the Peacham Congregational Church just up the road from the café.

Map it: strava.com/routes/2719935448112476256

11. NORTHEAST KINGDOM: THE LAKE LOOP — by Heidi Myers

The pro: Heidi Myers (along with Antony LaMoccia) is the force behind Rasputitsa, the epic gravel ride that has become the largest group ride in Vermont. A former marketing director at Louis Garneau (and now teaching at Sterling College), she’s helped make the Northeast Kingdom a gravel riding destination for folks from all over the country.

The ride: This 36-miler starts in Brownington at the majestic Old Stone House Museum and passes some of Vermont’s most scenic lakes. Built by Alexander Twilight, the nation’s first African American college graduate (Middlebury, 1823), the Old Stone House once served as a dormitory for Orleans County Grammar School. From this spot, you have a seven- mile, mostly-gravel pedal to the fjord- like Lake Willoughby, swim spot #1. From there, climb Penne Hill to explore what locals refer to as “the other side” of the lake. Circle Valley Mountain and connect with Route 16 at the Rainbow Farm which is an old farm with a rainbow faintly painted on it.

Route 16, though paved, is still void of heavy traffic. You pass the entrance of Crystal Lake for potential swim spot #2. Continuing on Route 16 takes you by Red Sky Trading, home to the best donuts in the state of Vermont. A quick pedal on Bean Hill brings you out in West Glover where Parker Pie sits humbly and makes for the perfect beer stop. A back road ride from there leaves you in Irasburg, former home of the deceased author, Howard Frank Mosher. Connect back to the Old Stone House via Orleans and pass Willoughby Falls, a fly fisherman’s paradise and where you might find trout jumping and spawning in the spring.

The swimming holes: Lake Willoughby, Crystal Lake, Willoughby Falls.

The bike shop: Nothing close, but the Hub Trailside in East Burke is my personal favorite.

The brewpub: Parker Pie serving up Hill Farmstead.

Refuel here: Donuts at Red Sky Trading.

Map it: strava.com/routes/2717819003611630786

12. MONTGOMERY: COVERED BRIDGES, HAUNTED HOLLOWS — by Daniel Jackson

The pro: An avid bikepacker and gravel route explorer, Daniel Jackson of Montgomery designed the gnarly gravel Fall Classic 200k route for New England Randonneurs and fancies himself the RouteMaster of Velo Vermont. As he says, “The chunkier the better, but I also love a fresh grade. “

The ride: This is a northern Vermont gravel ride along the shoulder of the Green Mountains. You’re on 90 percent dirt and climb over 100 feet per mile. The dirt is loose and often rutted, unless you catch the pass over Enosburg Mountain just after a fresh grade.

You’ll climb through Deep Gibou (an area some say is haunted) and cross the Cold Hollow Mountains where unmaintained Class 4 roads, covered bridges, and Highlander cattle predominate.

Montgomery boasts some of the best swimming holes in the state and the most covered bridges of any town. Stop at the Creamery Bridge swimming hole on the route and grab a drink in Montgomery after your ride.

The swimming hole: Local holes include: Hippie Hole, Three Holes, Creamery Bridge and others.

The bike shop: The Jay Cloud Cyclery and First Trax.

The brew pub: Check out The Inn, The Belfry, and The Snowshoe.

Refuel here: Bernie’s offers great Mexican on Monday and Thursday nights, and Donnie of First Trax makes stellar wood fired pizza. Sylvester’s General Store has everything you might need, nothing you don’t.

Map it: ridewithgps. com/routes/10253947