Old Bennington is technically part of the town of Bennington in southwestern Vermont. However, this neighborhood definitely feels like its own separate world, in a positive way. Walking down the street amidst stately homes and other buildings first erected in the 1800s and reading about the history of the location is almost like taking a step back in time. There’s a lot to appreciate here.

The Bennington Museum (and Trails)

Coming from downtown Bennington, the Bennington Museum would be one of the first attractions you’d see as a welcome to the world of old Bennington. Though it is temporarily closed at the moment I am writing this (due to the COVID-19 pandemic), normally it would be open from 10:00 AM – 5:00 PM, six or seven days per week depending on the season, with a $12.00 admission fee for adults, a discounted rate of $10.00 for students and seniors, and a delightful rate of “free” for all children age 17 and under. Inside the museum, the exhibits change as with most museums, but there are some mainstay featured galleries.

The museum is probably best known for its sizable collection of paintings by Grandma Moses, which is the first exhibit a visitor would encounter when entering the building. This is the only gallery in the whole museum where (non-flash) photography is not permitted so I cannot share any visuals here, but when I visited, I remember being really impressed by the details of community she created in her paintings, as well as appreciating being able to watch an interview with her conducted by Edward R. Murrow as part of the display.

Aside from the many paintings by Grandma Moses, there is plenty of other art to appreciate in the museum, including pottery, church relics, flags and textiles, and more modern art. As you can see below, I found the dolls and the classic car to be quite noteworthy.

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Next to the museum is a relatively small but lovely series of walking trails that is free for all to experience. On the George Aiken Wildflower Trail, various wildflowers are labeled with information and it is a sight to behold in the late spring and early summer. There is a children’s sculpture garden where kids (and adults) can create sculptures with rocks, pinecones, and other natural objects. You can also walk up to a meadow (featuring a unique crow sculpture) or down to a sweetly bubbling brook. Dogs are permitted with the usual expectations (keeping the pup on a leash, cleaning up any messes that may come up). The museum is worth a visit and following the experience with some fresh air on the trail only makes the experience better.

Old First Church and Cemetery

Right next to the Bennington museum is the Old First Church, which in its present form was built all the way back in 1805 (though an earlier meeting house for the congregation was built in 1763). In general, the church offers Sunday worship services, though again, things are a bit different now because of the coronavirus pandemic that has upended so much in our world lately. Even from the outdoors, the building is impressive and you can feel the history emanating from its steeple.

Right beside the church, one can enter can enter the Old Bennington Cemetery, which is also known as the Old First Church Cemetery. The majority of the graves here are the resting places of men and women who died hundreds of years ago, and their contributions to our country’s (and our state’s) history are described on various educational and informative plaques and other signage throughout the area. The most famous resident of this cemetery is none other than the poet Robert Frost, and there are several signs indicating the way to observe the grave of Frost and his deceased family members. Despite the negative connotations that a cemetery may instill, this is a lovely and peaceful place, where a person can learn a lot about various individuals from the past.

The Bennington Battle Monument

The Battle Monument in Bennington is arguably the most famous attraction in the whole town of Bennington, and its is certainly a notable landmark in the area of Old Bennington. At a little over 306 feet tall, this is the tallest man-made structure in the entire state of Vermont (and this fact really reinforces how different my new home is compared to my old neighborhood in New York City). The Monument was built in commemoration of the Battle of Bennington, which was a Revolutionary War battle that took place on August 16th, 1777. This August 16th date is known was “Battle Day” around these parts and various celebrations take place each year to honor this battle and the history of the town and state. (Personally, I’ve run in a “Battle Day” 5K and I’ve taken advantage of the free Monument elevator rides on this particular date.)

The Monument is surrounded by a circle (not surprisingly called “Monument Circle”) that includes residential homes, a gift shop, and a sprawling lawn with other historical statues and information. Many people use the area around the Monument for walks or runs – each time around is approximately a quarter mile (at least, according to my FitBit). It is free to appreciate from the outside, but a visit to the top generally involves a $5 admission fee (with the exception of “Battle Day” when anyone can come inside for free). Inside the Monument on the ground floor you can read the story of the Battle of Bennington and view a diorama or two depicting the fight. When you get on the elevator, a knowledgeable guide can tell you more about the battle and the Monument, and answer any questions that may come up. Once you reach the top, one has the opportunity to view green mountain landscapes of Vermont, New York, and Massachusetts, depending on where you are standing. Each view is breathtaking. This is definitely an attraction that adds value to the town, in terms of its beauty as well as in terms of its history.

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The same can be said for the whole area of Old Bennington in and of itself: it’s a historical haven, and a gorgeous one at that.

Freshly Vermont rating of Old Bennington (and its various attractions and landmarks): five out of five stars. ★★★★★