Vermont's Best Gravel Rides: A Cyclist's Guide

Embark on a Vermont Gravel Odyssey

Vermont, often celebrated for its autumnal foliage and maple syrup, also offers a cyclist's paradise for those who venture off the beaten path. The Green Mountain State boasts an extensive network of gravel roads, winding through picturesque valleys, past historic covered bridges, and alongside crystal-clear rivers. This guide, curated with insights from seasoned gravel professionals, unveils some of the most rewarding recreational gravel loops across Vermont. Each route is designed for exploration, offering a blend of challenging climbs, exhilarating descents, and opportunities to immerse yourself in the natural beauty and local culture of this beloved New England state. Whether you're a seasoned bikepacker or a curious newcomer to gravel riding, these 20- to 40-mile loops promise an unforgettable adventure.

The Appeal of Vermont Gravel

Gravel cycling in Vermont is more than just a sport; it's an experience. It's about the freedom of exploring quiet backroads, the thrill of discovering secluded swimming spots, and the simple pleasure of enjoying a craft beer at a local brewpub after a rewarding day in the saddle. These routes are chosen for their accessibility and the sheer joy they offer, allowing riders to connect with the landscape in a profound way. You might find yourself picking fresh blueberries, taking a refreshing dip in a river, or simply soaking in the panoramic views of rolling hills and working farms that characterize rural Vermont. The curated routes aim to showcase the diverse beauty of the state, from the historic battlefields of Bennington to the serene lakes of the Northeast Kingdom.

Expertly Curated Routes for Every Rider

We've tapped into the knowledge of Vermont's gravel cycling elite to bring you a selection of rides that truly capture the essence of the state. Each route is presented with a brief profile of the expert who recommended it, highlighting their connection to the area and their passion for gravel riding. Detailed descriptions of the rides, including key landmarks, challenging sections, and scenic highlights, will help you plan your perfect adventure. We've also included essential tips on where to refuel, find the best local brews, and, of course, where to take a well-deserved dip on a warm day.

1. Bennington: Holsteins, History, and Robert Frost

Joe Cruz, a renowned bikepacker and philosophy professor, offers a loop that encapsulates the quintessential Vermont experience. Starting at the Bennington Monument, this ride takes you through verdant wooded corridors, past working farms dotted with Holsteins, and along scenic stone-walled roads with burbling brooks. Expect classic Vermont-style climbing, particularly the ascent along Mt. Anthony. The route includes a thrilling descent into Pownal and a second climb on Ladd Brook Road, leading to pleasant rural roads showcasing signs of maple sugaring operations. The return to Bennington features rolling dirt roads, offering a final chance to enjoy the picturesque landscape before a potential visit to Robert Frost's grave at the Old First Church. For a refreshing break, a detour at mile 5.4 leads to a tranquil swimming hole.

Essential Stops:

• Swimming Hole: Fowler’s Way (approx. 0.3 miles past mile 5.4)
• Bike Shop: The Spoke in Williamstown, MA
• Brewpub: The Madison Brewing Co., Bennington
• Refuel: Ramunto’s, Bennington

Map: strava.com/routes/2717771383132915372

2. Slate Valley: Rail Trails and Pave

Created by Caitrin Maloney & Hardy Avery of Sustainable Trailworks, this 29-mile "Adventure" loop in southwestern Vermont is a true sampler of varied terrain. It features quiet gravel roads, challenging hills, and even a couple of rugged Class 4 "pavé" sections that will test your mettle. Enjoy expansive views, including the distinctive Bird Mountain, before a mellow cruise home on the D&H rail trail. The route traverses the Bird Mountain Wildlife Management Area, adding an element of wild adventure. This ride is ideal for those with fatter tires. The journey begins and ends in historic Poultney, with Tap’s Tavern a recommended post-ride stop.

Essential Stops:

• Swimming Holes: Numerous spots along the Poultney River (Route 140 east of Poultney) or Lake St. Catherine State Park.
• Bike Shop: Analog Cycles, East Poultney (unique, off-the-grid location)
• Brewpub: Taps Tavern, Poultney
• Refuel: East Poultney General Store

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

3. Woodstock: Rope Swings and Covered Bridges

Photographer and gravel rider Ansel Dickey highlights a route starting right from Woodstock that packs a punch within 40 miles. This ride is a journey through charming village centers, past classic Vermont general stores, and under historic covered bridges. A unique feature is a rope swing on Old River Road in Taftsville/Woodstock, offering a refreshing plunge into the Ottaquechee River. While the swing might be modest, it's a perfect spot for a quick cool-down. The route meticulously avoids pavement, ensuring a pure gravel experience.

Essential Stops:

• Swimming Hole: Ottaquechee River via rope swing on Old River Road, Taftsville/Woodstock
• Bike Shop: Drummond Cycles, Woodstock
• Brewpub: Brownsville Butcher and Pantry
• Refuel: South Woodstock General Store, Mon Vert Cafe (Woodstock)

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

4. Randolph: Braintree's 5 Climbs

Zac Freeman, a driving force behind the Rochester/Randolph Sports Trails Alliance, recommends the "Braintree 5" – a 35-mile ride with a substantial 5,000 feet of climbing. This ridge-line route offers stunning views of New Hampshire's White Mountains as you ascend Braintree Hill. Riders can pause at the historic Braintree Meeting House or cool off in Thresher Brook. The ride starts and finishes at The Gear House in Randolph, a hub for local trail information.

Essential Stops:

• Swimming Hole: River under the footbridge at Randolph Rec field
• Bike Shop: The Gear House (Randolph), RASTA Trail Hub
• Brewpub: Bent Hill Brewery (on the route)
• Refuel: The Black Krim Tavern, Randolph

Map: strava.com/routes/10660797

5. Norwich: Hills and Hidden Hamlets

Daniel Jordan, a founder of Vermont Bikepackers, shares a favorite 21-mile loop from his time working in Norwich. Don't let the distance fool you; this route packs in 2,700 feet of elevation gain and some seriously rugged terrain on Class 4 town highways. The ride begins with smooth dirt on local favorites like Bragg Hill and Chapel Hill, then tackles the challenging ascent of Sue Spalding Road, leading into deep woods. Prepare for some hike-a-bike sections, but the rewarding descent down Po Dunk Road, which crosses the Appalachian Trail twice, is well worth it. The route culminates with a climb to the Jericho Rural Historic District, a charming hamlet with rolling farmland, before a final gravel descent back to Norwich.

Essential Stops:

• Bike Shop: Cowbell Mobile Bike Shop (area), Mason Racing (Lebanon), Drummond Cycles (nearby)
• Brewpub: The Brewery at the Norwich Inn (Jasper Murdock Ales)
• Refuel: Dan & Whit’s (Norwich), King Arthur Flour (for coffee/pastry)

Map: ridewithgps.com/routes/33555875

6. Tunbridge: Big Views & Swimming Holes

Alex Buskey, founder of The Ranger gravel ride, calls Tunbridge home and recommends this all-time favorite loop. Starting from South Royalton (SoRo), the route is best enjoyed at a leisurely pace to fully appreciate the scenery. Highlights include a potential mid-ride swim in the First Branch of the White River below the Larkin Road Bridge, a beautiful pond near Quarry Road, and the challenging climb up Monarch Hill Road. The descent via Falls Hill Road leads to the iconic Howe Lane, one of Tunbridge’s most photographed spots. Several excellent swimming holes can be found along Route 110, offering perfect cool-down opportunities.

Essential Stops:

• Pre-Ride Buzz: First Branch Coffee, South Royalton
• Swimming Hole: Below Larkin Bridge, Tunbridge
• Bike Shop: The Gear House (Randolph), Green Mountain Bikes (Rochester)
• Brewpub: Upper Pass Beer Company / Worthy Burger, South Royalton
• Refuel: SoRo Coop (for snacks)

Map: strava.com/routes/2718328803651856044

7. Button Bay: Bovines & Battle Grounds / Addison County

Kris Dennan, owner of Gravel Tours, guides you along the shores of Lake Champlain with this scenic ride. Starting at Button Bay State Park, the route winds south on quiet farm roads, offering views of both the Green Mountains and the Adirondacks. You'll pass working dairy farms and roads historically used by the British military. Crossing the Crown Point Bridge provides access to Fort Henry and a potential swim in the lake. The terrain is rolling, with a mix of gravel and paved roads, and includes a climb towards Snake Mountain. The charming town of Vergennes offers ample choices for food and drink.

Essential Stops:

• Swimming Holes: Numerous options along Lake Champlain
• Bike Shop: Frog Hollow, Middlebury
• Brewpub: Hired Hand, Vergennes
• Refuel: The Bridge Restaurant (Crown Point Bridge)

8. Richmond: Blueberry Picking and Gorges

Chelsea Camarata, founder of Kaden Apparel, presents a delightful 19-mile loop starting at the Round Church in Richmond. This route is perfect for a quick ride or for those new to gravel, featuring a great climbing-to-downhill ratio. You'll pedal through beautiful farm fields and along quiet dirt roads. A highlight is the option to stop at Owl Head Farm for pick-your-own blueberries or enjoy a picnic at Gillett Pond. For those seeking a longer challenge, extending the route from Burlington via Governor Chittenden Road creates a 45-mile adventure. The Huntington Gorge and Bolton Potholes are also recommended swimming spots.

Essential Stops:

• Bike Shop: Hitchhiker Mobile Bike Shop (comes to you!)
• Brewpub: Stone Corral Brewery, Richmond
• Refuel: Sweet Simone’s, Richmond

Map: 19 mile: strava.app.link/qimnhutX77; 45 mile: strava.app.link/89lwN8BX77

9. Stowe: Sweet Gravel & Great Brews

While not his backyard, Ted King, the undisputed "Gravel King," makes a special trip to Stowe for this popular route. The Saturday morning 'Stowe Gravel Worlds' ride, running from late spring through early fall, is known for its mostly buff, sweet gravel roads. While generally smooth, there are a few brief Class 4 sections to keep you on your toes. The route is hilly but short enough to complete by late morning, often finishing at PK Coffee for a post-ride buzz. For a refreshing dip on a hot day, the West Branch is accessible.

Essential Stops:

• Swimming Hole: West Branch
• Bike Shop: Ranch Camp, Stowe
• Brewpub: The Alchemist or Idletyme, Stowe
• Refuel: PK Coffee (Stowe), Ranch Camp (Stowe)

Map: strava.com/routes/29080003

10. Peacham: Dairy Farms and Creemees

Former Tour de France pro Ian Boswell chose Peacham for its extensive network of quiet backroads, ideal for training. This quintessential 29-mile route, starting and ending at the Peacham Cafe, showcases the rolling hills of the Northeast Kingdom with sweeping views of the White Mountains. You'll pass active dairy farms, including Kempton Farm, which produces milk for Cabot Clothbound Cheddar. Be prepared for a challenging ride with over 4,000 feet of climbing. After your ride, enjoy a maple creemee and a swim at Harvey’s Lake, the site of Jacques Cousteau's first dive.

Essential Stops:

• Bike Shops: Village Sport Shop (Lyndonville), Onion River Outdoors (Montpelier) – BYO tools!
• Brewpub: Red Barn Brewing (Danville)
• Refuel: Peacham Cafe; West Barnet Quick Stop (for creemees)
• Swimming Hole: Harvey’s Lake

Map: strava.com/routes/2719935448112476256

11. Northeast Kingdom: The Lake Loop

Heidi Myers, a force behind the epic Rasputitsa gravel ride, highlights this 36-mile loop starting at the Old Stone House Museum in Brownington. The route meanders past some of Vermont's most scenic lakes, including the fjord-like Lake Willoughby, a perfect swimming spot. Ascend Penne Hill for stunning views and explore the "other side" of the lake. The ride connects with Route 16, a paved road with minimal traffic, passing Crystal Lake and Red Sky Trading (famous for donuts). A stop at Parker Pie for Hill Farmstead beer is a must before returning to the Old Stone House via Orleans, with a glimpse of Willoughby Falls.

Essential Stops:

• Swimming Holes: Lake Willoughby, Crystal Lake, Willoughby Falls
• Bike Shop: The Hub Trailside (East Burke)
• Brewpub: Parker Pie (serving Hill Farmstead)
• Refuel: Donuts at Red Sky Trading

Map: strava.com/routes/2717819003611630786

12. Montgomery: Covered Bridges, Haunted Hollows

Daniel Jackson, known as the "RouteMaster of Velo Vermont," recommends this northern Vermont gravel ride, characterized by 90% dirt and significant climbing. The route traverses loose and often rutted dirt roads, passing through Deep Gibou, an area rumored to be haunted, and the Cold Hollow Mountains. Montgomery is famed for its numerous covered bridges and exceptional swimming holes. The Creamery Bridge swimming hole is directly on the route, offering a convenient spot for a dip. After your ride, explore local watering holes in Montgomery.

Essential Stops:

• Swimming Holes: Hippie Hole, Three Holes, Creamery Bridge, and others
• Bike Shop: The Jay Cloud Cyclery, First Trax
• Brewpub: The Inn, The Belfry, The Snowshoe
• Refuel: Bernie’s (Mexican), Donnie of First Trax (pizza), Sylvester’s General Store

Map: ridewithgps.com/routes/10253947

Frequently Asked Questions

What is the best time of year for gravel riding in Vermont?

Late spring (May-June) and early fall (September-October) are generally considered the best times. Spring offers lush greenery, while fall provides spectacular foliage. Summer can be warm, but the higher elevation routes and frequent swimming holes make it enjoyable. Be aware that some Class 4 roads may be less passable after heavy rain or in early spring.

What type of bike is best for these routes?

A gravel bike is ideal, offering wider tires for comfort and traction on unpaved surfaces. Cyclocross bikes or mountain bikes with slicker tires can also work, but wider tires (35mm or larger) are highly recommended for comfort and control on the varied terrain, especially on Class 4 sections.

What should I pack for a Vermont gravel ride?

Essential items include a helmet, cycling computer or GPS device with the route loaded, water bottles or hydration pack, repair kit (spare tube, pump, tire levers, multi-tool), snacks, appropriate clothing layers, sunscreen, and a basic first-aid kit. A phone for emergencies and photos is also recommended.

Are these routes suitable for beginners?

Some routes, like the one near Woodstock or Richmond, are more beginner-friendly due to their shorter distances and less technical terrain. Others, like the Braintree 5 or the Norwich route, involve significant climbing and rugged sections, making them more suitable for experienced riders. Always assess your fitness level and choose routes accordingly.

Where can I find more information about gravel riding in Vermont?

Websites like bikepacking.com, gravelcyclist.com, and local cycling advocacy groups often have valuable resources, route suggestions, and event information for Vermont.

If you want to read more articles similar to Vermont's Best Gravel Rides: A Cyclist's Guide, you can visit the Automotive category.