It may come as a surprise to the casual observer/collector, but the Battle of Bennington commemorated on the 1927 Battle of Bennington - Vermont Independence Sesquicentennial Half Dollar was not fought in Vermont. The Battle of Bennington was actually fought in a field in Walloomsac, New York, which is about 5 to 10 miles northwest of Bennington, VT (different references cite different separating distances!).
Bennington, VT factored into event as the British, advancing under the overall command of General John Burgoyne and in need of replenishing stores and supplies, learned of stores being held in Bennington that would meet its needs. The town thus became a target location for two of Burgoyne's units, under the commands of Lieutenant Colonel Friedrich Baum and Lieutenant Colonel Heinrich von Breymann.
Upon learning of the British intentions regarding Bennington, the Vermont Council of Safety requested help from New Hampshire. The request was granted, and retired Continental Army Colonel, John Stark, was given the rank of Brigadier General along with the command of the forces that were to defend Bennington. Rather than wait for the British to attack Bennington, Stark led his troops out to face the British and met them in the fields of Wallomsac Heights in New York State. The battle, though its advantage wavered back and forth during its conduct, resulted in a decisive American victory.
The American victory at the Battle of Bennington, meant that the American supplies at Bennington were preserved and the British were denied a much needed resupply. It also stopped Burgoyne's march to Albany and the British attempt to isolate the New England colonies from the more southern colonies in an attempt to gain an upper hand in the War. Historians also believe Burgoyne's diminished troops, stores and supplies, as a result of the failure at Bennington, led to his failure at the Battle of Saratoga two months later - a turning point in the American Revolution for the Americans.
On the morning of August 16, 1927, the 150th anniversary of the Battle was commemorated in Walloomsac, NY via a joint program of the State of New York and the State of Vermont. Historical Markers were dedicated on the battlefield in Waloomsac, NY (including a relief map of the battlefield that featured indications of troop movements during the battle). In the afternoon, a parade and exercises were conducted in Bennington, VT along with an historical pageant presented in the evening.
Souvenir Program Cover - Battle of Bennington - 150th Anniversary - 1927
Souvenir Program - Battle of Bennington - 150th Anniversary - 1927 - Relief Map Marker
The 306-foot tall Bennington Battle Monument (located in Bennington, VT at the site of the 1777 supplies depot) was constructed as a memorial to the Battle and those who fought in it; the monument's cornerstone was laid in 1887 and the monument was completed and dedicated in 1891 - the Centennial Year of Vermont's Statehood.
Official Program - Vermont Statehood Centennial / Battle of Bennington Monument Dedication - 1891
Battle of Bennington - Vermont Independence Sesquicentennial Half Dollar

The Battle of Bennington - Vermont Independence Sesquicentennial Half Dollar was sponsored by the Vermont Sesquicentennial Commission, so its strong connection to Vermont is not a surprise. I've long wondered, however, if the folks in New York were also thinking about a commemorative coin and were simply beaten to the punch, or if they never even considered it?
For other of my posts about commemorative coins and medals, including more on the Bennington-Vermont half dollar, see:
Commems Collection.