Stories of Chester — the most-loved tales from our Facebook community: the bridges, inns, mills and families that built a Vermont town.
The Chester Vermont Historical Society preserves the history of Chester and its neighbors — in our museum on Main Street, in our monthly meetings, and in the stories our community tells. Our public Facebook group, some 3,000 members strong, shares old photos, postcards and personal stories day after day. A photograph surfaces from an album, a name gets remembered in the comments, and a piece of the town comes back to life.
Our featured stories below gather the posts the community loved most, ranked by their reactions. Each story is a summary written for this site, linked to the original post so you can read it in full and join the conversation.
Six threads run through everything the community loves most. Pick one to filter the stories below.
Rail-era hospitality: grand hotels, drovers, smorgasbords and fires.
Crossing the Connecticut, in wood and stone.
Bowls, lumber and the working valley.
Genealogy told the way families tell it.
Where Chester came for coffee and the news.
The valley as it was, mailed to the world.
Thirty-two stories, ranked by the community's reactions — counted across 280 of the group's posts. Every one was posted by Carla Westine.
Showing all 32 stories
No. 1A photo postcard of Rowell's Inn in Simonsville, white hand-lettering along the bottom in what looks like Harry Chapman's style — a period car out front and ladies in big hats completing the scene.
Photo via the Chester VT Historical Society Facebook group
Read the original post on FacebookNo. 2Before there was an iron bridge, there was this: a long wooden covered bridge carried on stone piers across the Connecticut River, linking Springfield, Vermont with Charlestown, New Hampshire. Just raising the stone supports mid-river — let alone spanning that distance in timber — was a serious undertaking. It is one of the most-loved images the community has shared.
Photo via the Chester VT Historical Society Facebook group
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No. 3A confident little girl in a flower-trimmed hat — Doris Jameson Eddy, whose lifelong love of blooms may well have started with that hat.
Photo via the Chester VT Historical Society Facebook group
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No. 4For many years the Weston Bowl Mill turned out wooden ware of every size and shape, and the scent of fresh-turned wood filled the air for visitors. At one time nearly every household in the area kept one of their bowls in the cupboard. Generations remember longtime employees Hazel Hale and June DeCell. This painting of the mill in snow, by Vermont artist Deus LaValle, graced the Bowl Mill's own advertising postcards.
Photo via the Chester VT Historical Society Facebook group
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No. 5A late-1940s newspaper article traces the history of the Chester store everyone now calls Smitty's — and the eighty years of keepers since only add chapters.
Photo via the Chester VT Historical Society Facebook group
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No. 6Granville and Evelyn Thompson of the Thompson Farm off Route 103 at the Okemo summit fire-lookout cabin in 1933 — one of a half-dozen young friends who climbed up for a picnic, photographed by neighbor Irma Horton.
Photo via the Chester VT Historical Society Facebook group
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No. 7On Route 11 toward Springfield, a thick stand of white pine hides a vanished industry: the Stevens & Thompson operation that logged, milled, and sold spruce log-cabin kits — later "Weird Wood" live-edge slabs — under manager Craig Reid.
Photo via the Chester VT Historical Society Facebook group
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No. 8This postcard view shows the Chester Inn in early autumn color, promoted as a stop on the Triple A Auto Tour. In the 1950s and 60s the inn was run by the Mackensen family, Swiss hosts who brought a European flair to Chester and were famous for their bountiful smorgasbord. Years later their son Warren visited the Historical Society and donated pieces from the inn — including a lovely copper charger plate — to the collection.
Photo via the Chester VT Historical Society Facebook group
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No. 9Londonderry-born Albert Buxton, captain in the 2nd U.S. Sharpshooters — wounded at Gettysburg in 1863, married Hattie Rice that August, reenlisted, and fell at the Battle of the Wilderness on May 6, 1864. His parents lost three sons to the war.
Photo via the Chester VT Historical Society Facebook group
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No. 10The impressive Hotel Chester stood in the Depot, across from the station, welcoming travelers and businessmen for four decades under a succession of proprietors. Locals also called it the Drover's Hotel, for the livestock trade it served. It burned down in 1880; today, Salon 2000 sits on the site.
Photo via the Chester VT Historical Society Facebook group · photo shared by Andre F Bourdeau
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No. 11Once upon a time, a restaurant filled the left-hand side of Town Hall's first floor. Proprietors came and went — George Hosmer, the Rhodes family, Mrs. Lake, Mrs. Monier — but the room stayed a favorite of Depot businessmen and travelers stepping off the train: a bite to eat, a cup of coffee, and the latest news around town. In the era of this photo you could buy cigars and candy there too.
Photo via the Chester VT Historical Society Facebook group
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No. 12Bobby socks, saddle shoes, and rolled-up sleeves: Everett "Slim" and Helen Crossman, Chester high school sweethearts of the class of 1949, leaning on a car. From Mary Bentley Williams' album.
Photo via the Chester VT Historical Society Facebook group
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No. 13A 1962 parade down Main Street — fabulous old cars, families watching, and in the background the Victorian William Pollard house, then home to Ruth's Gift Shop. Donated by the family of Henry F. Crocker Jr.
Photo via the Chester VT Historical Society Facebook group
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No. 14Chester High class of 1896; taught in the Popple Dungeon schoolhouse, trained as a nurse at Mary Fletcher Hospital, assisted Dr. Havens, then served as a WWI Army nurse in Florida and California — and stayed in La Jolla for life.
Photo via the Chester VT Historical Society Facebook group
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No. 15In June 1912 the Rawson family gathered to celebrate their town's centennial, and photographer E.M. Vaile took this portrait. A century earlier, Bailey Rawson and his eldest son had ridden in on horseback, felled the first trees, and cleared the land; the next year came a log house, then the rest of the family. Bailey — born in Uxbridge, Massachusetts in 1760, a descendant of Edward Rawson, secretary of the Massachusetts Bay Colony — had served as a fifer in the Revolutionary War. He lived to 88 and rests in the Rawsonville Cemetery; three of his sons farmed side by side in Jamaica.
Photo via the Chester VT Historical Society Facebook group
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No. 16In the glass-bottle era, soda pop was a special treat: twin sisters at a late-1940s picnic, each with a bottle their dad Ike opened with his church key. From Mary Bentley Williams' album.
Photo via the Chester VT Historical Society Facebook group
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No. 17Two Crocker-family photos of Chester's town pool in 1947 — then a cement-lined pond fed by Lovers Lane Brook, and for decades the place to learn to swim and cool off.
Photo via the Chester VT Historical Society Facebook group
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No. 18Long ago the Rhoades family settled at the far end of Popple Dungeon, Chester's storied back-country neighborhood. This studio portrait, from about 1886, shows Elmer Rhoades with his wife Etta Mary Good Rhoades and the two oldest of their five children — the beginning of a family woven deep into the Dungeon's story.
Photo via the Chester VT Historical Society Facebook group
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No. 19Drive down Route 103 toward Bellows Falls and you reach the junction with U.S. Route 5 — once home to The Highlands, a roadside restaurant and motel captured on this postcard. In the comments, members traded memories of its menus and prices: a whole era of Vermont road travel in one intersection.
Photo via the Chester VT Historical Society Facebook group
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No. 20Young Mary Ann Gilman would race from her hilltop house to the Depot to ride with engineer Andy, dreaming of becoming Vermont's first woman steam engineer; a 1970s video of the pair survives. She became a nurse instead — and helped countless patients.
Photo via the Chester VT Historical Society Facebook group
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No. 21From Society president Jon Clark's family collection: the Clarks on their Popple Dungeon steps — young Lauren in tall boots front and center, his father Cooledge behind him, brother John alongside.
Photo via the Chester VT Historical Society Facebook group
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No. 22Seventy years ago someone made four West Chester farm boys — Peter (now the Society's historian), Chris, Tim, and Francis — little gum holders, color-coded so each knew his own. Carefully saved, they look brand new today.
Photo via the Chester VT Historical Society Facebook group
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No. 23Postcard "P7245 Depot Hill, Chester, Vt.": the dirt road toward the Depot before paving — today's Route 103 North near Coach Road and First Avenue, shared after a long modern construction season on the same stretch.
Photo via the Chester VT Historical Society Facebook group
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No. 24Students of the one-room Peaseville School in Andover, donated by the family of Mary (Bentley) Williams — Mary second row, second from left; front-row Reino confirmed the year as 1941, and the group is still identifying the rest.
Photo via the Chester VT Historical Society Facebook group
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No. 25Chester-born Raymond J. Hall (1892), raised around his father's School Street livery, clerked and then managed hotels, and rode Paul Adams' horses to prize after prize — with Lady Luck he won the Green Mountain Horse Association 100-mile ride.
Photo via the Chester VT Historical Society Facebook group
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No. 26A postcard of Grafton's "Old Stone Fort" rock formation in Village Park, 1923 painted inside the entry — the year Gertrude Daniels gifted the land and funds for the park. Shared by Andre F. Bourdeau.
Photo via the Chester VT Historical Society Facebook group · shared by Andre F. Bourdeau
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No. 27Chester High's class of 1915 on their senior trip: an open-top tour bus in Washington, D.C., the Hotel Vendome on Pennsylvania Avenue, the Capitol, the Monument — and a session of Congress.
Photo via the Chester VT Historical Society Facebook group
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No. 28Historian Peter Farrar's grandparents Philip and Isabel Tieman left suburban New Jersey after the Crash for a 91-acre Cavendish farm — brick farmhouse, barns, three brooks, and spring water — they named Windy Hill.
Photo via the Chester VT Historical Society Facebook group
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No. 29A June 2, 1972 newspaper clipping of Steamtown locomotive No. 127 — when you could tell the time in Chester by the train whistle, and Depot businesses planned around the rush when the train pulled in.
Photo via the Chester VT Historical Society Facebook group
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No. 30Found in the archive box after the Popple Dungeon event: a small 1920 photo of a car passing the roadside watering trough, black album paper still clinging to its edges.
Photo via the Chester VT Historical Society Facebook group
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No. 31In 1894 Nelson and Mrs. Snell celebrated 50 years of marriage at the Trebo Road homestead — the same year marked 100 years since Nelson's grandfather Elisha, a Revolutionary War veteran, bought the land in 1794. Over 100 guests came.
Photo via the Chester VT Historical Society Facebook group
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No. 32Mary Bentley Williams' younger brother Edwin — Peaseville School standout at spelling and math, ski-jumping and slalom winner, 4-H calf raiser, excused early at sugaring season; Chester High class of 1951.
Photo via the Chester VT Historical Society Facebook group
Read the original post on FacebookTwelve more favorites from the group — each one a door into another Chester story.
The museum, the meetings and the membership that keep Chester's heritage alive.
230 Main Street, Chester, VT
PO Box 118, Chester, VT 05143
Hours: Memorial Day through Columbus Day, Sundays 1–4 PM.
Meetings: every 4th Thursday (except November and December) at the Old Academy building on Main Street.
$10 individual · $15 family
“Your membership helps preserve Chester's heritage for future generations.”