The village outside our front door, stop by stop — transcribed in full from the 1991 Bicentennial brochure, with the original hand-drawn map. 125 Bridge House sits in the middle of it.
Waitsfield was chartered in 1782 and first settled in 1789 by General Wait and family. The General Wait home is number one on the list, but you can make it the first — or the last — stop on your tour of historic Waitsfield Village.
The whole loop is walkable in about an hour at an easy pace, and every stop below is within a few minutes of our door on Bridge Street. Most of the buildings are private homes: please admire them from the road.
Descriptions are reproduced as printed in 1991, including a few original typos (marked [sic]). Anything described as a current business or use may have changed since.
“The township owes its name to General Benjamin Wait, the first settler and proprietor of the town. Waitsfield is almost precisely at the geographical center of the state of Vermont, and tradition has it that the commissioners to locate the state capital ‘struck their stake’ (almost precisely) where the village now stands. But General Wait declared ‘he wouldn’t have his meadow cut up’ and so he saved the town from that honor.”
“White cottages are to be seen on either side of the valley, and about there are plenty of the evidence of thrift and comfort… The landscape is pronounced, even by strangers, to be picturesque and charming beyond many others in Vermont —”
The original hand-drawn map of Waitsfield Village: Bridge Street and the Great Eddy of the Mad River at the center, VT Route 100 running north–south, the escarpment and ledge to the west, and the original road alignments dotted in. Tap the map to enlarge and pinch to zoom.
The brochure’s numbering is itself the route. Numbers climb as you walk south along the east side of Route 100, out Bridge Street to the east, back over the covered bridge, and then north up the west side of Route 100, closing the loop within sight of stop #1. Gaps in the sequence are properties that were passed but not written up. The full loop is roughly one mile on mostly level ground — allow 60 to 90 minutes at a reading pace.
Begin at the north end of the village. The General Wait House sits near the cemetery on the west side of Route 100; the rest of this leg runs down the east side of the road toward Bridge Street.
The first frame house in Waitsfield was built by the town's founder and namesake, General Benjamin Wait, on the old road, which was west of the present Rt. 100. In this house the town was organized in 1794. About 1830, it was moved down to its present location near the cemetery, where the general was buried. At that time the second story was added.
In 1847 it came time to replace the Village District one-room school building, which had stood north of Benjamin Wait's house on the old road. A two-story wooden structure with a belfry was built. There was one room on each floor, the upper one for the more advanced students. In 1906, it became a two year high school. In 1917 the larger front section was added and the high school was extended to four years.
Mr. Shaw originally settled on Dana Hill in 1830 and died in 1880. By 1900 George Olmstead occupied this house. It continues to be a private residence.
This Classsic [sic] Cottage style house was built by John Walton. Beginning in 1882, it was occupied for many years by Dr. Henry J. Howe for both dwelling and medical office.
William Morrill Pingry (Pingree) built this house, where he lived and practiced law for nine years before moving to Weathersfield. Later Dr. David Carlisle Joyslin lived here and carried on the practice of medicine until his death in 1874. The second story may have been added about 1880.
This brick house was “built by Roderick Richardson, Jr., the son and business partner of Roderick Richardson, who was responsible for the establishment of the village as a commercial center”. For many years it was the home of Judge Jonathan H. Hastings. More recently it was occupied by the family of Walter E. Jones, who assisted his brother, Matt Bushnell Jones, in writing the History of Waitsfield.
The first Congregational Meeting House was erected on the Common in 1807. By 1844 the building was in disrepair and the center of town activities had moved from the Common to the valley. After much dissension between the parishoners [sic] in the eastern part of town and those in what had developed as the village, a site on Mill Hill in front of the present cemetery was chosen for the second Meeting House, which was built in 1846.
This location proved unsatisfactory and the building was taken down. As much material as could be saved was used in 1874 in the construction of the present building on land given by Judge Hastings. Designed by the Reverend James H. Babbitt, pastor of the church from 1868 to 1876, this building has been called the best example of a Romanesque Revival style church in the state.
This was originally a small cape with a separate barn. In later years an addition was built to connect them. Many people now living would refer to it as the home of John Kingsbury, who lived here and carried on his trade of blacksmith in the old shop across the bridge.
Turn east at the Bridge Street intersection and cross the Great Eddy on the covered bridge. The numbering runs out and back: 18, 20 and 21 are on the north side as you walk east, then 22 through 25 bring you back west along the south side. Read the bridge itself, #26, on the return crossing. Stops 28 and 30 sit just west of the river near the Route 100 intersection.
Roderick Richardson, Sr., built this brick house for his son, Dan. The present owner found the date 1830 burned into a board in the attic. It was known for many years as Campbell's Tavern.
Edwin A. Dumas, born in Waitsfield in 1828, was a mill owner and operator. He operated mills in this immediate area.
About 1900 the house was purchased by Walter Moriarty, owner of the sawmill which, together with the grist mill, had been built in 1829 and 1830. Miramar Ski Club is now on the site of the grist mill and the sawmill was behind it at a right angle. The canal to provide water power for both ran under the road where the iron railing of a bridge can be seen.
As printed in 1991 — the Miramar Ski Club reference may no longer be current.
The wooden part of this building is the older part and was occupied as a store, kept by George Frederick Kidder in 1820. When he was appointed postmaster in 1822, it also served as a post office. About 1835 it was made into a dwelling.
The original part of this house first served as “the little red schoolhouse” located at the fork of the roads leading to the Common and to East Warren. Sometime in the early 1860's, the building was moved to the village and converted to a dwelling. About 1865, it was acquired by the Congregational Society for a parsonage.
John Walton, a blacksmith, built yhis [sic] house near the shop (#25) he had built ten years earlier.
John Walton's blacksmith shop began as a small gable-roofed building. Over the years, it was enlarged and changed into a flat-roofed garage. Some people now living remember it as John Kingsbury's blacksmith shop.
The first bridge spanning the river at the Great Eddy was built before 1796. The present structure, completed in 1833, is the second oldest covered bridge in use in the State of Vermont today and the oldest in continuous use in the state.
This building was erected by W. Jasper Walton in 1848, and was utilized for hardware, tinsmithing, and plumbing. More recently it was owned by “Doc” Bisbee as a hardware store and sheetmetal shop.
This building, erected by Elisha Foster, was originally located at the “foot of the dugway” in Irasville. It was moved in 1851 by Roderick Richardson, Jr. to its present site. The large brick basement was used by the Town for its annual town meetings and other gatherings for many years.
From the Bridge Street intersection, continue to the south end of the village for stops 43 through 48, then turn north and work back up the west side of Route 100. The numbers climb as you go, ending at #57 within sight of where the tour began.
Description not captured in the available panels.
Printed on the map at the south end of the village. Its description is on a brochure panel we haven’t photographed yet.
This is the oldest house in Waitsfield Village still on its original site. It was built by Roderick Richardson in 1817 as a center chimney cape. This house was owned for many years by the Fullertons.
Mr Boyce was a Methodist minister but took up the life of a merchant and operated a store in what is now the Masonic Lodge building from 1862 until his death. It was then carried on by his son until his death in 1903
In 1855 Mr. Campbell acquired this house which had been built by Roderick Richardson. In the same year he became proprietor of the hardware store in #28.
This brick building was erected in 1831 by Roderick Richardson and was occupied as a store by him and his son until it was partially destroyed by a fire in 1845. The present brick structure then built is unique in that it has three oriel display windows cantilevered on granite sills. These are the original windows in the front of the building and the only ones of their type in Vermont today.
This house served as the Town Clerk's office for many years and Richardson James Gleason also kept a post office in this same building from 1861 to 1889.
This house, now known as the Village Grocery, was built around 1845 and was up to and through 1873 the J.W. Richardson Estate. This was a well-kept village residence occupied by H. W. and Elizabeth McAllister in the very early 1900's.
As printed in 1991 — the “Village Grocery” use may no longer be current.
Description not captured in the available panels.
Printed on the map on the west side of Route 100 between #51 and #53. Its description is on a brochure panel we haven’t photographed yet.
There are persons in Waitsfield who say that this house and the Andrew Bigelow house were built by the same person around 1840. This may be true because of their general similarity.
This house was built by James W. Richardson around 1840 and was occupied for many years by Andrew W. Bigelow, who was a harness maker and livery stable proprietor. The Potting Shed at the rear was originally a little harness shop erected on The Common in 1810 by Roderick Richardson. It was later removed to the Village Square, and then to its present location around 1840.
This square brick structure was built in 1836 by the Union Meeing [sic] House Society as a one-story church building. It has been occupied since 1903 by the local chapter of the Odd Fellows, who remodeled it into a two-story structure. Today it is the home of the Valley Players Theater.
The Valley Players theater is closed for building repairs and safety upgrades, expected to reopen in 2027.
This low brick dwelling was built by Dan Richardson in the 1840's, after he had acquired much of the original Wait farm. The house has always been a private residence.
Now occupies the restored General Wait House — stop #1 — and the contact for brochure permissions.
The 1995 town purchase, the ISTEA grant, and the Burley Partnership restoration toward the 1793 plan.
Listed on the National Register September 6, 1974 (ref. 74000261). Single-span Burr truss, about 105 feet.
Longest clear Burr truss span in Vermont, plus the 1973 repair campaign that saved it.
Listed August 11, 1983 (ref. 83003224) — about 70 acres along VT 100 and Bridge Street.
The original 1793 town center about a mile east — a good way to continue your visit.
The surrounding agricultural landscape, listed in 1994.
The company bought its portion of the Odd Fellows building in 1988.
Matt Bushnell Jones, History of Waitsfield, 1782–1908 (referenced at stop #12), and Rev. Perrin B. Fiske, The History of the Town of Waitsfield, 1882 — both available through the Waitsfield Historical Society.
125 Bridge House sits inside the historic district, a two-minute walk from the covered bridge.
Text transcribed from “Waitsfield Village Historic District Walking Tour,” a Bicentennial Project, 1791–1991. Original text and illustrations by their respective authors and artists; the illustrator’s signature on the “Old ‘Downtown’ Area” drawing is not fully legible in our copy and will be credited once confirmed. Transcribed and published online in 2026, with thanks to the Waitsfield Historical Society. Historical descriptions reflect conditions as of 1991. Reproduced for visitor reference — if you hold rights to this brochure and would like a correction or removal, please contact us.