RoutesPlannerFeaturesUpdates
App
Login or Signup
Get the App
Login or Signup
Routes
Road cycling routes
United States
Vermont
Orange County

Williamstown

The best road cycling routes around Williamstown

5.0

(1)

86

riders

5

rides

Road cycling routes around Williamstown offer a diverse landscape characterized by hilly terrain, New England woodlands, and picturesque river valleys. The region provides a mix of entirely paved roads and routes incorporating substantial dirt or gravel sections. Cyclists can find challenging climbs, such as those leading to Mount Greylock, alongside flatter paths through bucolic river valleys. This varied topography makes Williamstown a compelling destination for road cycling.

Best road cycling routes around Williamstown

  • The most popular road cycling route is…

Last updated: October 5, 2026

5.0

(1)

64

riders

#1.

Baker Pond – O'Maddi's Deli & Café loop from Northfield

64.9km

02:48

520m

520m

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Navigate with deviceSend to Phone
Save
Moderate

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.
Sign up for free

Moderate road ride. Good fitness required. Some segments of this route may be unpaved and difficult to ride.

Moderate

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

Hard

3

riders

Moderate road ride. Great for any fitness level. Some segments of this route may be unpaved and difficult to ride.

Moderate

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Williamstown

Hiking around Williamstown

Cycling around Williamstown

Running Trails around Williamstown

Tips from the Community

Lisa
June 29, 2025, Cross-Vermont Trail (Route 2)

For now, at least, this section of the Cross-Vermont Trail overlaps with Route 2. At least you have the pretty Winooski River for company!

0

0

Lisa
June 29, 2025, Junction Road

A nice stretch of gravel road — nothing stressful to ride. It ties into the Cross-Vermont Trail and the Montpelier Bike Trail.

0

0

Sue
June 19, 2025, Winooski West Path

The Winooski West Path is a 2.6-mile paved multiuse trail that follows along the scenic Winooski River through a mix of forest and urban landscapes. This trail is perfect for walking, biking, and running, as it's mostly flat with views of the water the entire way. It's easily accessible from downtown, making it an ideal spot for a relatively short hike—whether you're taking a lunch break or simply want to spend an hour enjoying a stroll along the beautiful waterfront.

0

0

Lisa
February 25, 2024, Websterville Quarry

This working quarry is a major landmark in Gnome Man's Land, a section of Millstone Trails that has lots of mountain biking trails in it. Two of the trails near the quarry — Abbott's Run and Beaver Run — offer the only biking that's really easy enough for touring tires. Keep an eye out for trucks entering and leaving the quarry.

0

0

maniboyflex
February 21, 2024, Baker Pond

Baker Pond is a peaceful lake surrounded by a vibrant green forest, with beautiful fall colors. The pond covers an area of 35 acres, and it is easily accessed from the road, with a gravel ramp for boat access. The access to the pond is an open area and can be a nice place to take a break. This pond belongs to the Vermont Fish & Wildlife Department and it is a popular destination for fishing.

0

0

Great view of one of the ponds in the Barre Town Forest. The forest is unique in that it is found in an old quarry. The ponds were created in the large holes created by the old quarry.

0

0

mtm05005
September 22, 2023, Small Falls

Small water fall created by a dam on the Winooski River. There is a good view of the falls from the pedestrian footbridge that crosses the river from Vine Street.

0

0

Zachary
June 2, 2021, Red Hen Bakery

Great spot for breakfast pastries, coffee, sandwiches and other ride snacks. They have a bike rack out front in the summer and lots of seating. Don't miss it!

0

0

Frequently Asked Questions

How many road cycling routes are available around Williamstown?

Our guide features 4 road cycling routes around Williamstown, offering a mix of moderate and difficult rides. These routes are primarily located in the scenic areas of Vermont, near towns like Northfield and Barre.

What kind of terrain can I expect on road cycling routes near Williamstown?

The routes around Williamstown, particularly those in nearby Vermont, offer diverse terrain. You'll find hilly landscapes, rolling farmlands, and picturesque river valleys. While some routes are entirely paved, others may incorporate substantial dirt or gravel sections, catering to various preferences and fitness levels. Expect challenging climbs and scenic descents.

Are there any challenging road cycling routes for experienced riders?

Yes, Williamstown and the surrounding Vermont area are known for challenging climbs. Our guide includes two difficult routes, such as the Websterville Quarry loop from South Barre, which covers over 100 km with significant elevation gain. Another demanding option is the Osgood Hill – Websterville Quarry loop from South Barre, featuring over 1000 meters of ascent.

What natural features or landmarks can I see along the road cycling routes?

While cycling the routes around Williamstown, you can enjoy scenic views of woodlands, farmlands, and river valleys. Some routes pass near natural highlights such as the Montpelier Municipal Forest and the Northfield Municipal Forest. You might also encounter unique sights like the Brookfield Floating Bridge or picturesque pond views.

Are there any family-friendly or easier road cycling options in the area?

While the routes in this specific guide are rated moderate to difficult, the broader Williamstown region (Massachusetts) offers easier options like the Ashuwillticook Rail Trail or the Mohican Recreational Path, which are broad, flat, and paved, suitable for casual riders and families. For routes in this guide, the Winooski West Path – Junction Road loop from Barre is a moderate option with less elevation gain compared to the more difficult routes.

What is the best time of year for road cycling in Williamstown?

The best time for road cycling in the Williamstown area is typically from late spring through early autumn (May to October). During these months, the weather is generally pleasant, and the New England foliage provides stunning scenic backdrops, especially in the fall. Be prepared for varying conditions, as the hilly terrain can lead to cooler temperatures at higher elevations.

Are there any circular road cycling routes?

Yes, all the road cycling routes featured in this guide are circular loops. This allows for convenient starting and ending points, such as the Baker Pond – O'Maddi's Deli & Café loop from Northfield or the Cross-Vermont Trail (Route 2) – Red Hen Bakery loop from South Barre.

What do other cyclists say about road cycling in Williamstown?

The Williamstown area is highly rated by the komoot community, with an average score of 5.0 stars. Cyclists often praise the region's diverse terrain, challenging climbs, and the stunning natural beauty of the New England woodlands and river valleys.

Are there places to eat or refuel along the routes?

Many routes, particularly those starting or passing through towns like Northfield or Barre in Vermont, offer opportunities to refuel. For example, the Baker Pond – O'Maddi's Deli & Café loop from Northfield explicitly mentions a deli and café in its name, indicating convenient stops for food and drinks.

Is there public transport access to the road cycling routes?

While specific public transport options directly to the start of every route may vary, the towns where these routes begin, such as Northfield and Barre in Vermont, generally have some level of public transport connectivity. However, for maximum flexibility, driving to the starting points is often the most convenient option for cyclists.

Where can I find more information about the Williamstown area?

For general information about Williamstown, Massachusetts, including local attractions and community resources, you can visit the official town website at williamstownma.gov. This can be helpful for planning your visit beyond the cycling routes.

Most popular routes around Williamstown

Hiking around Williamstown

Most popular attractions around Williamstown

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now
Store rating

Explore more

Browse the best Road cycling routes in other regions.

Thetford Hill State ParkThetford Hill State ForestWells RiverNewburyFairleeUnion Village Dam Recreation AreaBradfordRandolphChelsea

Nearby adventure guides

Things to Do around South Barre

background

Get ready to conquer new peaks

Sign up for Free
Explore
RoutesRoute plannerFeaturesRedeem a voucherHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy