Rides and Routes Around Bennington

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Dark Woods - A 29.22 mile loop that goes over North Pownal Road, often called "Dark Woods". The reverse loop is also available. It makes for a fun ride either way! 

Covered Bridge Ride - A 14.5 mile ride that brings you over all three of Bennington's covered bridges. A short, but scenic ride, from the shop! 

Bennington and Saratoga Battles Ride - This 84 mile ride features a trip around the iconic Bennington Monument, a climb up to the Bennington Battlefield, and a ride all the way to Victory, NY, where the Saratoga monument was built. 

Battle of Bennington - This is a 28-mile version of the Bennington and Saratoga Battles ride. It leaves out the Saratoga monument, but features the two components of the Battle of Bennington (the Bennington Monument and the Bennington Battlefield). 

River Road/Johnson Hill - A 30.6 mile ride that climbs over River Road and blasts down River Road. The ride goes into White Creek, NY, then takes you home via Silk Road. 

Searsburg/North Adams Loop - This 55 mile ride starts off with a climb from Woodford, VT into Searsburg. TA left turn takes you all the way down into North Adams, MA. Route 7 and South Stream Road will bring you back to Highlander Bicycle. 

Chapel Hill/Buck Hill Loop - Two variations of this 16 mile ride are available. One climbs up Buck Hill, and one bombs down it. Both routes are fun! 

South Stream #1 - This 17.5 mile ride follows a rolling route around South Stream. There are three variations of the South Stream ride, with this being the longest option.

South Stream #2 - This is the medium version of the South Stream ride. It is a rolling 13.1 miles long. 

South Stream #3 - The shortest and final version of the South Stream loops. It is only 6.3 miles long. 

Kingsley/Greylock/Petersburg Pass - This ride is a challege. It is 106.28 miles long and has 12,774 feet of climbing, including three notorious climbs; Kingsely Road, Greylock, and Petersburg Pass.