Roxbury, Vermont: Take the Dirt Road to Fall

There comes a weekend every October when Vermont seems almost unreasonable.

The maples go red.

The hills turn orange and gold.

Morning fog settles into the valleys.

And every road that normally exists simply to get somewhere suddenly becomes somewhere worth going.

That's when I'd head to Roxbury.

Not because it has Vermont's most famous foliage road.

Quite the opposite.

I'd go because it doesn't.

🍁 Start in Roxbury Village

Roxbury is small.

The town was chartered in 1781, and its geography has always played an outsized role in its story. Mountains surround the narrow valley, with Route 12A and the railroad following the easier ground through town. Town of Roxbury VT

Spend a few minutes in the village before heading toward the mountain.

There's one particularly good stop here.

☕ Stop at the Roxbury Country Store

The building that houses the Roxbury Country Store has operated as a country store since the mid-1800s.

Randy Whitney has owned it since 1997.

And this is still very much a Vermont country store rather than someone's modern interpretation of one.

Coffee.

Groceries.

Gas.

Propane.

Local maple syrup.

Hunting and fishing licenses.

It's also an official Vermont big-game reporting station.

The Town of Roxbury calls it the "beating heart of Roxbury."

That's a pretty good endorsement. Town of Roxbury VT

Grab something for the road.

Because now we're going up.

🚗 Turn Onto Warren Mountain Road

This is the drive I've been saving for October.

Warren Mountain Road leaves the valley and begins climbing west toward the Roxbury Gap.

And then the pavement ends.

That's important.

The Roxbury side of Warren Mountain Road is dirt.

It's steep in places, and conditions can change with rain, grading, washboarding, mud and eventually snow. A September 2026 examination of the road described the Roxbury side as susceptible to ruts and washboarding by fall. Compass Vermont

So this isn't a road I'd recommend blindly following because your GPS found a shortcut.

Check the weather.

Check road conditions.

Take your time.

And if conditions aren't appropriate for your vehicle, turn around.

There are plenty of beautiful Vermont roads without turning foliage season into an extraction operation.

🍂 Now Look Around

When conditions are good, the reward becomes obvious.

The road climbs away from Roxbury through forest toward the height of land separating Roxbury from Warren and the Mad River Valley.

Maple.

Birch.

Beech.

Evergreen.

Openings in the forest reveal mountains beyond mountains.

The Town of Roxbury specifically includes Warren Mountain Road among the roads featured in regional fall-foliage and bicycle tours. Town of Roxbury VT

But the reason I like it isn't simply the foliage.

It's the transition.

You begin in one Vermont valley.

Climb a mountain.

And come down into another.

💧 Find Roxbury Falls

Before you get too far up the mountain, watch for the area around Carrie Howe Road.

Roxbury Falls is located on Warren Mountain Road near the base of Carrie Howe Road.

The Town notes that it's especially impressive when water levels are high. Town of Roxbury VT

This is a good example of why the Roxbury drive works.

You're not moving from major attraction to major attraction.

The road itself keeps giving you little reasons to stop paying attention to the destination.

🌸 Then Look for a Farm on the Mountain

Farther along Warren Mountain Road is Moonlight Mountain Farm.

Nick and Kristen arrived on Roxbury Gap in 2019 and built a small mountain farm around flowers, pastured lamb, forest-grown shiitake mushrooms, chickens and farm stays.

During the growing season, their roadside stand sells flowers and other available farm products.

And in October, flowers and foliage get to compete for attention. Moonlight Mountain F

We'll tell their full story in Blog #2.

🏔️ Cross the Gap

Eventually, something interesting happens.

Warren Mountain Road becomes Roxbury Mountain Road.

Same mountain.

Different town.

And a very different road surface.

The Warren side is paved, descending toward East Warren and the Mad River Valley. Warren's transportation planning identifies Roxbury Mountain Road as one of only four effective routes into and out of town. CVRPC

That's one of my favorite Vermont details.

Roxbury calls the road Warren Mountain Road because that's where you're going.

Warren calls it Roxbury Mountain Road because that's where you came from.

The mountain sits between them.

🥪 Stop in East Warren

When you reach East Warren, the East Warren Community Market makes a natural stop.

As of October 2026, the market is open daily from 8 a.m. to 8 p.m. at the intersection of Roxbury Mountain Road and East Warren Road. East Warren Community Market

From there you can continue toward Warren Village and Route 100.

And suddenly you're in a part of Vermont many visitors know much better.

That's precisely why I like starting in Roxbury.

⭐ Nathan's Hidden Gem: Drive From One Valley Into Another

My hidden gem isn't a particular overlook.

It's the whole crossing.

Roxbury → Warren Mountain Road → Roxbury Gap → East Warren → Warren Village.

Don't rush it.

And don't judge the drive by mileage.

Stop when there's a safe place to stop.

Look backward occasionally.

The view behind you may be better than the one ahead.

And remember that people actually live on this road.

Foliage season shouldn't turn somebody's driveway into a scenic overlook.

Nathan's Fall Foliage Route

Here's the route I'd make out of it:

Northfield → Roxbury → Warren Mountain Road → East Warren → Warren Village → Waitsfield → Moretown → Middlesex

That connects several communities we've already explored.

Start in Northfield and take Route 12 south toward Roxbury.

Spend some time in Roxbury Village.

Cross Warren Mountain Road when conditions permit.

Continue through East Warren.

Drop into Warren Village.

Then follow the Mad River Valley north through Waitsfield and Moretown before finishing toward Middlesex.

It's not about getting back quickly.

That's what Interstate 89 is for.

This drive is about choosing the slower road on purpose.

What Does Living in Roxbury Feel Like?

The foliage also reveals something about Roxbury real estate.

This is a mountainous town.

A beautiful mountain road in October can be a very different road in February or mud season.

For someone considering property here, I'd want to understand much more than the house:

Road classification and maintenance.

Driveway grade.

Snow removal.

Four-wheel-drive access.

Well and septic systems.

Internet and cell service.

Emergency access.

Distance to employment and services.

Topography.

Drainage.

And what that road actually looks like after six inches of snow.

That's not a reason to avoid rural property.

It's a reason to understand the lifestyle you're buying along with it.

Take the Long Way Home

Vermont foliage doesn't need much help from us.

Sometimes the best plan is simply choosing a road that gives you enough time to notice it.

In Roxbury, that road climbs west out of the village.

Part of it is dirt.

It crosses a mountain.

It changes names at the town line.

And sometime in October, when the leaves cooperate, it can make the long way home feel like exactly the right way to go.