Weatherhead Hollow Pond loop from Brattleboro

The Weatherhead Hollow Pond loop from Brattleboro offers a rewarding road cycling experience through the scenic, rolling terrain of southeastern Vermont. This moderate 36.6-mile (58.9 km) route, with 2282 feet (695 metres) of elevation gain, can typically be completed in about 2 hours and 43 minutes. It's an excellent choice for cyclists with good fitness looking for a picturesque ride that blends challenging climbs with gentler stretches.

What to expect on Weatherhead Hollow Pond loop from Brattleboro

As you pedal the Weatherhead Hollow Pond loop, you'll journey through rural landscapes rich with natural beauty, passing by scenic ponds and winding through forested sections. The route showcases the broader Brattleboro area's sweeping pastoral scenery and river valleys. While much of the ride is paved, be prepared for varied elevation changes, including challenging climbs and descents. It's important to note that some segments of this route may be unpaved and difficult to ride, adding an adventurous element to the road cycling experience. This ride is best suited for those who appreciate diverse terrain and are ready for a moderately challenging day on the bike.

Planning your visit

Before heading out, be aware that while the route is generally considered a road cycling path, some sections might be unpaved. This means you should be prepared for varied surfaces and potentially more challenging conditions on those segments. As with any ride in Vermont's varied topography, checking weather conditions beforehand is always a good idea, especially considering the elevation changes. There are no specific permits mentioned for this route, but always respect private property and local regulations.

Trail details

• Distance: 36.6 miles (58.9 km)
• Elevation gain: 2282 feet (695 metres)
• Difficulty: moderate
• Estimated time: 2 hours and 43 minutes