A Perfect Fall Day in Bennington, Vermont

For a small shire town, Bennington, Vermont is packed with interesting things to do. This is thanks in part to its storied past. Founded in 1749, Bennington was the first town in what would eventually become the State of Vermont. (Hence the town slogan, “Vermont Begins Here!”) At the time, however, America was a set of thirteen increasingly restive British colonies. A mere thirty years after the town was founded, the Battle of Bennington served as a turning point in the Revolutionary War and was the first instance of untrained colonial militia trouncing a professional European force. Today, the town is about as peaceful as it gets.

I began my day in Bennington with a plan to trounce the area’s best blueberry pancakes. This led me to Sunny Side Diner. A local favorite since 2012, the staff seemed to be on a first-name basis with every patron but me. I devoured a short stack of fluffy pancakes bursting with whole fresh blueberries and drenched in real Vermont maple syrup. If only every day could start with such a treat!

blueberry pancakes with vermont maple syrup at sunny side diner

After breakfast I drove to the Bennington Museum to learn more about the town’s history. What I found was a fabulous assortment of Americana that engrossed me for hours. The Bennington Museum is home to the largest public collection of paintings by Grandma Moses. Although she didn’t begin painting until well into her seventies, Grandma Moses went on to become one of the country’s most beloved folk artists. Her colorful scenes depict rural life at its most charming. Other famous pieces at the museum include the Jane Stickle Quilt made in 1863 from 5,602 pieces of fabric; an original 1925 Martin Wasp automobile; and the Bennington Flag, one of the oldest American flags in existence.

battle of bennington — Scene depicting colonial militia rounding up prisoners after winning the Battle of Bennington

The 1863 Jane Stickle Quilt is made from 5,602 individual pieces of fabric // Bennington Museum, Vermont

will moses painting — This is a folk painting by Will Moses, great-grandson of Grandma Moses. No photos were allowed of her works.

Around the corner from the museum stands the Old First Church. Established in 1763, it is the oldest Protestant church in Vermont. It was also the first to promote America’s founding “separation of church and state” principle. The current building dates to 1805 and is maintained without the use of any government funds despite its historic landmark status. The money for the church’s initial construction came from the sale of the first floor pews. (A church volunteer likened it to buying box seats at the opera.) The adjacent cemetery is the final resting place of early town settlers, Revolutionary War soldiers, and renowned poet Robert Frost.

The Old First Church in Bennington, Vermont

Grave of American poet Robert Frost and his family in Bennington, Vermont

A short drive up Monument Avenue leads to the Bennington Battle Monument. The 306-foot-tall obelisk commemorates the Battle of Bennington which took place nearby on August 16, 1777. The American side was led by General John Stark and included Vermont’s own Green Mountain Boys, a militia founded by local patriot Ethan Allen. They soundly defeated a British detachment under the command of General John Burgoyne, who would surrender a few months later at the Battle of Saratoga. The monument is the tallest structure in Vermont and topped with an observation deck from which three different states can been seen.

There are three picturesque covered bridges in Bennington. The Henry Bridge is the most historic, dating to 1835. The adjacent Henry House Inn was built in 1769 and is one of the oldest surviving structures in Vermont. The Paper Mill Bridge is the longest, with a span of 125 feet. The Silk Road Bridge completes the trio. They all cross the Walloomsac River about halfway between Old Bennington and North Bennington and are easy to find.

henry house inn bennington — Henry House Inn, one of the oldest buildings in Vermont

You can’t visit Bennington in autumn without stopping by the Apple Barn. In addition to apples picked from the orchard, you’ll find freshly baked pies, apple cider donuts, maple ice cream, and other mouthwatering treats. This is also a great place to pick up local souvenirs like Vermont maple syrup and cheddar cheese.

A few miles further south on Route 7 I found a much less commercial farmstead with a fabulous fall pumpkin display. The shop inside the rickety barn didn’t have as large a selection, but the prices were lower and service more personal.