Top Things to See in Bennington VT: Historic Sites, Museums, and More

Nestled in the picturesque landscapes of Vermont, Bennington is a charming town that promises a delightful blend of history, culture, and natural beauty. My recent visit to Bennington felt like stepping into a living history book, where each street and landmark tells a fascinating story. This quaint town offers a unique opportunity to experience the essence of New England, with its well-preserved historical sites, scenic streets, and welcoming atmosphere.

The journey began at the renowned Bennington Museum, a treasure trove of art and artifacts that beautifully capture the spirit of Vermont. From the riveting exhibits of the Revolutionary War in the Military Gallery to the heartwarming collection of Grandma Moses paintings, the museum offers an enriching glimpse into the past. As I moved on to the Old First Church and the Bennington Center Cemetery, I was deeply moved by the historical significance and serene beauty of these sites. The church, built in 1805, and the cemetery, with its historic gravestones and famous residents, provided a poignant connection to the town’s early days.

Strolling up Historic Monument Avenue and visiting the towering Bennington Battle Monument were equally captivating experiences. The avenue, lined with grand homes and historic landmarks, felt like a walk through time, while the monument, Vermont’s tallest structure, stood as a proud tribute to a pivotal battle in American history. Each stop on my tour revealed a different facet of Bennington’s rich heritage, making my visit a memorable and enriching experience. Whether you’re a history enthusiast, an art lover, or simply seeking a picturesque getaway, Bennington has something special to offer.

First Stop, the Bennington Museum

Grandma Moses in Modern Company at Bennington Museum | Observer

A Treasure Trove of History and Art

My adventure in Bennington began at the renowned Bennington Museum, a place that beautifully captures the essence of Vermont’s history and artistic heritage. As soon as I walked through the doors, I was greeted by a rich array of exhibits that transported me back in time.

The Military Gallery

One of the highlights was the Military Gallery, which provided a detailed overview of the Battle of Bennington and the town’s role in the Revolutionary War. The exhibit featured an impressive collection of Vermont-made firearms and artifacts from the battle, offering a vivid glimpse into the past.

Grandma Moses Collection

The museum also houses the largest collection of paintings by Grandma Moses, a beloved American folk artist. Her works, with their vibrant colors and charming depictions of rural life, truly captured my heart. Each painting seemed to tell a story of its own, reflecting the simplicity and beauty of Vermont’s countryside.

The Martin Wasp Automobile

Another intriguing exhibit was the Martin Wasp automobile, a vintage car made in Bennington in 1925. This elegant vehicle showcased the ingenuity and craftsmanship of the early 20th century, highlighting Bennington’s contributions to automotive history.

Temporary Exhibitions

In addition to its permanent collections, the Bennington Museum regularly hosts temporary exhibitions that delve into various aspects of Vermont’s art, history, and innovation. During my visit, I was fortunate to catch an exhibit on Vermont’s role in the abolitionist movement, which was both enlightening and inspiring.

Visiting the Old First Church and the Bennington Center Cemetery

Bennington Cemetery - Picture of Bennington Centre Cemetery - Tripadvisor

A Landmark of Religious Freedom

After immersing myself in the history at the museum, I made my way to the Old First Church, a significant landmark that stands as a testament to the separation of church and state in Vermont. Built in 1805, this beautiful structure replaced a simpler pine meetinghouse where the Protestant congregation had gathered since 1762.

Architectural Beauty

The church’s architecture is a sight to behold, with its elegant design and historical significance. I learned that the construction of the church cost $7,793.20, funded by selling box pews on the first floor to parishioners for prices ranging from $40 to $500. The upper pews, known as the Free Gallery, were reserved for children and visitors.

The Bennington Center Cemetery

Behind the Old First Church lies the Bennington Center Cemetery, one of the oldest cemeteries in Vermont. Walking through the cemetery felt like a journey through time, as I encountered the graves of notable historical figures and beautifully crafted tombstones.

Robert Frost’s Final Resting Place

One of the most poignant moments of my visit was seeing the grave of Robert Frost, Vermont’s most famous poet. Buried alongside his family, Frost’s resting place is a place of reflection and homage to his literary legacy.

Historical Gravestones

The cemetery is also the final resting place for three former governors, many Revolutionary War soldiers, and even a Loyalist executed in 1778. The gravestones themselves are works of art, adorned with historic death imagery like winged skulls, cherubs, and intricate floral motifs. Each stone tells a story, providing a glimpse into the lives and times of those who lived centuries ago.

Stroll Up Historic Monument Avenue

Catamount Tavern Site Bennington, Vermont - YouTube

Leaving the church and cemetery, I embarked on a leisurely stroll up Monument Avenue, a street lined with grand historic homes and landmarks dating back to the late 1700s. The avenue is like an open-air museum, showcasing the architectural styles and stories of Bennington’s past residents.

The Catamount Tavern Site

One of the most fascinating stops on Monument Avenue is the site of the former Catamount Tavern, marked by a larger-than-life copper catamount statue. The tavern, originally known as Fay’s House, played a crucial role during the Revolutionary War as the headquarters for Ethan Allen and the Green Mountain Boys, and later for General John Stark.

The name “Catamount Tavern” came about when residents placed a real stuffed catamount on the signpost to intimidate unwelcome New Yorkers. Though the original tavern burned down in 1871, its legacy lives on through the stories and the symbolic statue.

Historic Homes and Buildings

As I continued my walk, I admired the historic homes along Monument Avenue, each with its unique charm and history. Notable buildings include the Old Academy, originally built as a school in 1819, and the Fay-Brown House, a stone blacksmith shop constructed in 1781. These structures offer a glimpse into the architectural evolution and daily life of Bennington’s early residents.

The Bennington Battle Monument

Bennington Battle Monument to Undergo Multiyear Renovation | True 802 |  Seven Days | Vermont's Independent Voice

A Towering Tribute to History

No visit to Bennington would be complete without seeing the Bennington Battle Monument, the tallest structure in Vermont. Standing at an impressive 306 feet and 4½ inches, this monument commemorates the pivotal Battle of Bennington, fought on August 16, 1777.

The Battle of Bennington

The Battle of Bennington was a turning point in the American Revolution, where General John Stark and his militia, along with the Green Mountain Boys led by Seth Warner, defeated a British force comprised of Indians, Loyalists, and German mercenaries. This victory paved the way for another British defeat in Saratoga, marking a significant moment in the fight for American independence.

Monument Construction

The idea to commemorate the battle with a monument began in the early 1800s, but it wasn’t realized until many decades later. The cornerstone of the monument was laid on August 16, 1887, and it was constructed using Sandy Hill Dolomite quarried in Hudson Falls, New York. The capstone was placed in 1889, and the monument was dedicated in 1891.

An Unforgettable View

Under normal circumstances, visitors can take an elevator to the observation tower at 188 feet, offering breathtaking views of Vermont, New York, and Massachusetts. Although my visit coincided with COVID-19 safety precautions that restricted inside visits, I still marveled at the monument’s exterior, spotting ammonite fossils embedded in the dolomite.

The grounds around the monument are perfect for an afternoon picnic, providing a serene setting to reflect on the historical significance of this site.

Final Thoughts

The Most Beautiful Spots in Bennington, Vermont ⋆ Back Road Ramblers

My journey through Bennington, Vermont, was an unforgettable experience that deepened my appreciation for American history and the beauty of Vermont. From the rich collections at the Bennington Museum to the poignant tranquility of the Old First Church and its cemetery, the historic charm of Monument Avenue, and the awe-inspiring Bennington Battle Monument, every stop on my tour offered a unique perspective on the past.

Whether you’re a history enthusiast, an art lover, or simply looking for a picturesque getaway, Bennington has something to offer. I left with a heart full of memories and a newfound connection to the stories that shaped this charming town. I highly recommend taking the time to explore Bennington and discover its many treasures for yourself.


Bennington, Vermont is a gem that offers visitors a rich tapestry of history, culture, and scenic beauty. My journey through this charming town was nothing short of enchanting. Each landmark and attraction, from the Bennington Museum’s treasure trove of artifacts to the historic Old First Church and its storied cemetery, provided a deep dive into the past. Strolling up Monument Avenue felt like walking through the pages of a history book, while the towering Bennington Battle Monument offered a tangible connection to a pivotal moment in America’s fight for independence.

Whether you’re a history buff, an art enthusiast, or simply someone who appreciates the charm of a quaint New England town, Bennington has something to captivate and inspire you. The town’s welcoming atmosphere, combined with its wealth of historical and cultural sites, makes it a must-visit destination. So, pack your bags, set your sights on Bennington, and prepare to step back in time and create memories that will last a lifetime.