Discover 5 of the Oldest Cities in Vermont

Vermont and New Hampshire are neighboring states in New England that some people have difficulty distinguishing on a map. It’s really easy, though, once you realize that Vermont has a V shape. Both states are popular tourist destinations, especially in the fall when the turning leaves create a spectacular display. In this article, we will learn more about this gorgeous and historic New England state by exploring some of its oldest cities.

1. Brattleboro, 1724 (population 12,184)

Brattleboro was the first town in Vermont. It was named after a colonel from Boston who never even visited the town that honored him. It developed into a thriving, industrious city with a variety of mills, factories, and the largest organ company in the United States. An “asylum for the insane” and a “water curative health resort” were also located there. These may have played a role in attracting some interesting characters.

A local printer named Thomas James claimed to have been in contact with the spirit of Charles Dickens, who commissioned him to finish The Mystery of Edwin Drood. Rudyard Kipling married a woman from Battleboro and settled in Dummerston, where he wrote The Jungle Book. Kipling wrote critically of the weather, the nosiness of small-town people, the long working days of farmers, men killed seeking fortunes elsewhere, and women battling loneliness and depression. These were common conditions for people in the 19th century, no doubt made worse by the grueling Vermont winters.

Visit the Estey Organ Museum to learn about a company that created music across the country. Check out the Creamery Covered Bridge, made of spruce lumber. Visit the Brattleboro Museum and Art Center, which includes works by Wolf Kahn and Andy Warhol. Take a walk on Retreat Trails south of Green Mountain National Forest. The trails wind through the forests north of Massachusetts. Along the way, you can explore a historic cemetery and the Retreat Tower or follow the path to the top of the town’s ski jump, which hosts the Harris Hill Ski Jump, an annual event. Finally, stop by the Robb Family Farm Sugar House to buy locally-made maple syrup.

2. Westminster, 1735 (population 3,016)

Westminster is on Vermont’s eastern border with New Hampshire. It had a colorful history in the Revolutionary War era. A month, before the war started at the Battle of Lexington, the Westminster Massacre occurred in 1775. During this incident, local landowners were at risk of losing their land due to back taxes. Armed with clubs, residents occupied the courthouse to demand their case be heard. Two protestors were killed in the ensuing fight with authorities. The next day, 500 “Green Mountain Boys” arrived from south of Westminster and Massachusetts and took the judge and other authorities as prisoners. The British were unable to reassert authority over Westminster due to the Revolutionary War. In 1777, Vermont rejected land claims from New York, New Hampshire, and Connecticut and declared itself an independent Republic. The capital of the country was located in Westminster for 14 years until Vermont became a state in 1791.

Things have quieted down in Westminster these days. Visitors can stay in the Sanctuary Garden Bed and Breakfast, eat French and American cuisine at The Restaurant at Burdick’s, buy fresh produce at Alyson’s Orchard, and pick up specialty items and gifts at Allen Brothers Farms. Be sure to take the kids to Santa’s Land, a family-owned theme park with train rides, a fun house, mini golf, a carousel, and a giant slide.

3. Bennington, 1749 (population 15,333)

The city of Bennington, Vermont was established as a result of the “Great Awakening” religious revival led by Jonathan Edwards in the 1730s in Massachusetts. A group of 60 religiously inspired colonists started the town and rapidly planted farms and opened businesses. When their land rights came under question by the British authorities, the locals organized a militia called the Green Mountain Boys. This group, headquartered in Bennington, protected the rights of the citizens. In 1777, they helped the Patriots win a decisive battle against a larger British force that included 800 German mercenaries. This was the first time the rebels beat a professional standing European army in an open battle. It greatly boosted the morale of the American forces.

Visitors to the city can visit the Bennington Battle Monument, the tallest man-made structure in the state. The Old First Church, established by the original founders, has the grave of poet Robert Frost in the cemetery. The Robert Frost Stone House Museum preserves the home he lived in from 1920-1929. Here, he composed one of his most famous poems, “Stopping by Woods on a Snowy Evening.” He actually wrote it on a June morning! The Bennington Museum has a special exhibit on the city’s history and a permanent Grandma Moses gallery.

4. Bellows Falls, 1753 (population 2,747)

Bellows Falls was originally named Great Falls but was renamed for a landowner, Colonel Benjamin Bellows. It was the site of the first bridge built over the Connecticut River and also the British-built Bellows Falls Canal, one of the first canals built in what is today the United States. With the arrival of the railroad, Bellows Falls developed into a mill town with numerous industries. Wealthy business owners in the Victorian era built stately homes and mercantile buildings that have been preserved and can still be enjoyed today.

These are some of the sites you can enjoy if you visit Bellows Falls today:

• Bellows Falls Petroglyph Site has large boulders with pre-colonial Native American petroglyphs carved on them.
• Sherwin Art Glass has glassmaking demonstrations with hand-sculpted and blown glass and a retail gallery.
• River Artisans Cooperative is where you can admire and purchase works of 32 local crafters including wildlife photography, quilts, potter, glassware, knitting, ironwork, and more.
• Morning Star Perennials & Nursery is a tree farm and nursery selling flowers, shrubs, fruit trees, and more.

5. Manchester, 1761 (population 4,484)

Manchester was settled on land better suited for grazing than farming. After its settlement, the surrounding hills were dotted with over 6,000 sheep. The economy was also sustained by iron mines, marble quarries, and the lumber industry. After the Civil War, Manchester became an affluent resort area and continues to be popular today, particularly with visitors from New York and Connecticut. It’s also the home of snowboarding. Jack Burton Carpenter, one of the inventors of the sport, developed his snowboard design in Manchester and operated his company, Burton Snowboards, there until 1982.

Here are some of the noteworthy attractions of Manchester:

• Mount Equinox – the highest peak in the Taconic Range. You can drive to the top of it via a privately-owned toll road from Memorial Day weekend through October 31st.
• Hildene – the family home of Robert Todd Lincoln, who was the only one of Abraham Lincoln’s sons to live to adulthood.
• Equinox Golf Resort and Hotel – was formerly Equinox House, where Mary Lincoln and her sons Robert and Tad stayed in the summer of 1863 to escape the heat of Washington D.C.
• American Museum of Fly Fishing – has over 40,000 items related to fly fishing. A must-visit for anglers!

When Will You Visit Vermont?

Vermont has a unique history as one of the few states that were once if only briefly, independent countries. But it also played an outsized role in the events of the American Revolution that helped the whole country achieve independence. Vermont today welcomes you to enjoy a slice of Americana. So the remaining question is, when will you visit Vermont?

Summary of 5 of the Oldest Cities in Vermont

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