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Routes
Road cycling routes
United States
Vermont
Washington County
Waterbury

Roxbury Gap – Great Eddy Covered Bridge loop from Waterbury-Stowe

Routes
Road cycling routes
United States
Vermont
Washington County
Waterbury

Roxbury Gap – Great Eddy Covered Bridge loop from Waterbury-Stowe

Hard

5.0

(9124)

9,125

riders

Roxbury Gap – Great Eddy Covered Bridge loop from Waterbury-Stowe

04:47

93.4km

1,050m

Road cycling

Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride. The starting point of the route is accessible with public transport.

Last updated: May 26, 2026

Tips

The surface for a segment of your route may not be suitable

Some segments of your route comprise a surface that may not be suitable for your chosen sport.

After 48.7 km for 3.18 km

Waypoints

A

Start point

Train Station

Get Directions

1

8.15 km

Red Hen Bakery

Highlight • Cafe

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!

Tip by

2

34.7 km

O'Maddi's Deli & Café

Highlight • Cafe

3

51.8 km

Roxbury Gap

Highlight • Mountain Pass

This scenic pass between the Green Mountains offers stunning views and a gateway to charming towns and outdoor adventures.

Tip by

4

64.9 km

Great Eddy Covered Bridge

Highlight • Bridge

Great Eddy is the oldest covered bridge still in operation in Vermont. It was built in 1833 and to this day is one of the main routes in and out of Waitsfield.

Tip by

5

87.3 km

Cross-Vermont Trail (Route 2)

Highlight (Segment) • Trail

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!

Tip by

B

93.4 km

End point

Train Station

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Way Types & Surfaces

Way Types

59.2 km

33.3 km

525 m

316 m

100 m

Surfaces

90.0 km

3.19 km

274 m

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (720 m)

Lowest point (130 m)

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Weather

Powered by Foreca

Today

Sunday 19 July

22°C

13°C

0 %

Additional weather tips

Max wind speed: 15.0 km/h

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Description

If you're seeking a formidable challenge paired with classic New England charm, the Roxbury Gap – Great Eddy Covered Bridge loop from Waterbury-Stowe is a road cycling route that truly delivers. This difficult 58.1 miles (93.4 km) loop packs in 3458 feet (1054 metres) of elevation gain, typically taking around 4 hours and 47 minutes. It's a serious test for experienced cyclists looking for a rewarding day in the saddle.

What to expect on Roxbury Gap – Great Eddy Covered Bridge loop from Waterbury-Stowe

This route immerses you in quintessential Vermont, transitioning from serene pastoral valleys to sweeping Green Mountain vistas. The centerpiece is the Roxbury Gap, a significant Category 2 climb that will test your legs with sustained gradients reaching up to 16% on the west side and 14.1% on the east. After conquering the gap, you'll descend towards the historic Great Eddy Covered Bridge in Waitsfield, a picturesque landmark over the Mad River. The East Warren Road section offers well-paved surfaces and stunning views of the Green Mountains, often passing charming farms and unique structures like a round barn. This ride is best suited for cyclists with very good fitness who appreciate a challenging climb and varied terrain.

Planning your visit

Be prepared for mixed surfaces on this Roxbury Gap Great Eddy Covered Bridge loop road cycling route; while much of the route is paved, the east side of Roxbury Gap might include gravel sections. The best time to cycle Roxbury Gap Vermont is typically from late spring through early fall, when the weather is favorable and the scenery is at its peak. Parking for cycling Roxbury Gap Great Eddy Covered Bridge is generally available in the Waterbury-Stowe area where the loop begins. Always check local road conditions, especially after heavy rain, as some unpaved sections can become more difficult.

Trail details

  • Distance: 58.1 miles (93.4 km)
  • Elevation gain: 3458 feet (1054 metres)
  • Difficulty: difficult
  • Estimated time: 4 hours and 47 minutes

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