Chimney Point & State Historic Site

The Chimney Point loop offers road cyclists a truly scenic journey, combining the natural beauty of Lake Champlain with the dramatic backdrop of the Adirondack Mountains. You'll enjoy expansive water views and the unique experience of crossing the Lake Champlain Bridge, making for a memorable ride through varied landscapes.

This moderate 33.9-mile (54.5 km) route, with 1618 feet (493 metres) of elevation gain, typically takes around 2 hours and 22 minutes to complete. The trail is almost entirely paved, making it ideal for road bikes. Consider starting your ride in the morning to enjoy the best light and avoid any potential afternoon winds.

What truly sets this route apart is its blend of natural beauty and rich history, highlighted by the Chimney Point & State Historic Site. This location has been continuously inhabited for nearly 9,000 years, offering a fascinating glimpse into Native American, French Colonial, and early American cultures right along your cycling path.

The Middlebury Falls – Middlebury College Quad loop offers a fantastic road cycling experience, blending urban charm with natural beauty. You'll pedal past the impressive Middlebury Falls, through the scenic Middlebury College campus, and into the rolling hills and woodlands surrounding Middlebury, with glimpses of the Green Mountains. This moderate 49.2-mile (79.2 km) route features 2052 feet (625 metres) of elevation gain, typically taking around 3 hours and 23 minutes to complete, making it a solid choice for cyclists looking for a rewarding day out.

Starting your adventure in Middlebury is convenient, with parking available in town. The route is predominantly paved, suitable for road bikes, and offers a great way to explore local landmarks. For the most breathtaking views, especially of the Green Mountains, aim to ride during the vibrant fall foliage season. There are no special permits required, making planning your visit straightforward.

What makes this route truly stand out is its unique combination of downtown Middlebury's character, the natural spectacle of the falls, and the expansive beauty of one of New England's most picturesque college campuses. It's a microcosm of the diverse terrain found in the Middlebury area, providing a varied and engaging ride that highlights both the town's charm and Vermont's stunning landscapes.