Vermont doesn't make the riding easy, and that's the point. The Green Mountains run straight up the middle of the state — no detours, no polite bypasses — and every worthwhile road either climbs them, crosses them through a gap, or follows a river corridor that was carved around them. Plan a route here and you're really planning around the terrain.

The Spine: Route 100

Start with Vermont Route 100 — The Spine. It runs roughly 216 miles from the Massachusetts border north to Newport, tracing the eastern flank of the Green Mountains the whole way. The southern section has off-camber corners and reducing-radius bends through dense forest. North of Killington the road opens up into hill country with a dipping, swinging rhythm that works well at mid-pace. Route 100 isn't a point-to-point blast — it's the connector that makes everything else on a Vermont tour work. The gap roads branch off it; the valley towns hang off it; the food stops cluster around it. Two or three days on VT-100 with side trips onto the gaps is a reasonable framework for a full Vermont tour.

The Gap Roads

The gaps are where Vermont riding gets technical. The Appalachian Gap — VT-17 eastern approach packs 53 turns into 3 miles of climbing with grades that hit 15% and steeper, topping out at 2,369 feet. Pull off at the Appalachian Gap Summit and you get a clear look west toward Lake Champlain and the Adirondacks. VT-17 connects naturally with VT-100 and VT-125 to form the classic Mad River Loop — roughly 66 miles, four road numbers, and the best concentration of technical pavement in central Vermont.

Middlebury Gap — VT-125 is the quieter sibling: a designated Vermont Scenic Road that winds through the Green Mountain National Forest, cresting at 2,144 feet with the Breadloaf Wilderness to the north. Brandon Gap — VT-73 is quieter still, reaching near 2,200 feet between Brandon and Rochester with a cliff-face pull-off at the summit where you can look straight up at the face of Mount Horrid.

Lincoln Gap Road, branching west off VT-100 near Warren, is worth knowing about. Vermont's own tourism office calls it the steepest paved mile in the United States — the western approach off VT-116 is where that grade lives. Coming from Warren via the eastern approach, the climb builds progressively before the gradient gets serious near the top. It's short, it's fully paved on the eastern side, and it drops you out near Lincoln village. Ride it as a deliberate detour from VT-100, not as a casual through-route.

The Notch

Smuggler's Notch (VT-108) is a category of its own. The 5-mile notch section between Stowe and Jeffersonville squeezes between cliff faces and boulders at single-lane width, with no commercial traffic permitted. It is closed from late fall through late spring — check VTrans before you plan around it. The Smugglers Notch Summit pull-off gives you a few minutes to walk among the glacially deposited rocks and look up at the walls. Go slowly through the notch itself; the road surface and the lane width require your full attention.

Southern Vermont

The Molly Stark Scenic Byway — VT-9 runs 40 miles east-west across the southern tier from Brattleboro to Bennington, climbing to roughly 2,400 feet near Hogback Mountain with forested switchbacks and a 100-mile, three-state panorama from the Hogback Mountain Scenic Overlook. The Stone Valley Scenic Byway — VT-30 runs 111 miles north from Brattleboro to Middlebury through the West River valley and the Manchester area — a long day's ride or a solid segment on a multi-day southern Vermont loop.

VT-15 from Jeffersonville east to St. Johnsbury is a different character entirely: roughly 50 miles of long sweeping curves following the Lamoille River, with Mount Mansfield visible to the south. It's not technical in the way the gaps are, but the road surface is well-kept and the rhythm is steady. Good for putting in miles after a tight morning on VT-108.

Stops Worth Planning Around

American Flatbread at Lareau Farm is the most consistently cited food stop on the VT-100 corridor — wood-fired flatbreads in a 19th-century farmhouse setting on 25 acres in Waitsfield, open Thursday through Sunday evenings. If you're on a southern VT run, the Creemee Stand in Wilmington on Route 100 North is a straightforward seasonal stop: soft-serve custard with Vermont maple syrup, gravel parking, no fuss. The Warren Covered Bridge is a short detour off VT-100 just north of where Lincoln Gap Road turns off — a 57-foot Queenpost truss structure from 1880 that motorcycles fit through easily.

For riders who want to add a summit climb, Mount Equinox Skyline Drive off Route 7A in Sunderland is a private paved toll road that ascends 3,248 feet over 5.2 miles — the longest privately owned paved toll road in the United States. The road has grades up to nearly 15%, several pull-offs, and five-state views from the top. Open seasonally from Memorial Day through late October.

Rally

The Green Mountain Rally, run by BMW Motorcycle Owners of Vermont, takes place every September at Camp Thorpe in Goshen — a few miles off Brandon Gap Road (VT-73). Now in its 40s as an annual event, it caps attendance at around 250 riders and operates as a self-guided format: cabin and tent camping, four home-cooked meals, live music, and roads in every direction. It's not a loud spectacle rally; it's a small-group riding weekend in one of the better-positioned spots in the state.

Plan Your Ride

Vermont's season runs late May through mid-October with confidence; shoulder months can be fine but the gap roads see frost early in fall and linger in mud season in spring. Smuggler's Notch closes for an extended window each year — verify the VTrans seasonal status before building an itinerary around it. Helmet use is required by Vermont law. Cell coverage is patchy in the gaps and the Northeast Kingdom; download your route before you go.