Viewpoint and Rock Wall on Taconic Road

The Greenwich, CT to Bedford, NY loop offers a challenging yet incredibly scenic touring cycling experience, perfect for those who appreciate varied terrain and beautiful landscapes. You'll pedal through charming woodlands, past serene reservoirs like Byram Lake, and even catch glimpses of coastal views along the Long Island Sound. The route is known for its "punchy CT climbs" and significant elevation changes, making it a favorite among the local cycling community for its blend of physical demand and natural beauty.

This is a difficult 32.6-mile (52.5 km) ride with 1959 feet (597 metres) of elevation gain, typically taking around 3 hours and 28 minutes to complete. It's best suited for cyclists with very good fitness levels who are comfortable with sustained ascents and descents. While mostly paved, some longer versions might include unpaved sections, so check your route carefully. Autumn is a particularly popular time to ride, thanks to the vibrant foliage, but warmer months also offer pleasant conditions with refreshing breezes.

This loop is a highly regarded route within the active cycling scene of both Fairfield and Westchester counties, attracting experienced riders looking for advanced cycling trails. Beyond the physical challenge, you'll pass through historical sites like the Bedford Village Historic District and enjoy scenic viewpoints throughout. It's a rewarding journey that showcases the natural features and charming communities of Connecticut and New York.