Windham County Vermont Guilford Fair Festival

Labor Day weekend closes the Vermont summer, and in Guilford it closes with a fair. Across its two full days, Sunday and Monday, the grounds off Weatherhead Hollow Road fill with cattle and exhibit tables. Its own homepage calls it a celebration of rural life and all things good in Guilford, Vermont. One caution: no fair-side record calls this event a Windham County Fair, and the fair never claims that name. The county enters only because Vermont law places Guilford inside Windham County, whose shire town hosts nothing here.

A Town’s Fair, Run by the Town

The Guilford Fair is the Labor Day-weekend agricultural fair of the town of Guilford, Vermont, which a fair-supplied description says honours Vermont’s agricultural traditions. Its standing programme: a horse draw, cattle and horse shows, sheep shearing demonstrations, live music, and exhibits of produce, flowers, handiwork and hobbies. The name forms stay unmerged: its own site, the state agriculture list and the town all call it the Guilford Fair; its own homepage heads the year form 2026 Guilford Fair, one edition’s heading and never the standing name; and its vendor application prints the capitalised form GUILFORD FAIR in that document only.

The organiser is the Guilford Fair Association, the form running through the fair’s own current record, whose cheques in the vendor paperwork are payable to it. The town layer adds that the Association owns the fairgrounds, all Guilford citizens being members of it. A second corporate form, Guilford Fair Inc., belongs to history: the Official History of Guilford records incorporation under that name on September 2, 1946, a directory layer repeating the form without making it the current name. David Franklin appears as President in the vendor application’s insurance block and as the town layer’s rental contact, and two other named people appear only as form contacts; none of those individuals is the organiser in any layer. The Broad Brook Grange administers one baking contest, and the Guilford Recreation Club owns the park next door; neither runs this fair.

County geography is settled by statute, not by the fair. Title 24, chapter 1, section 14 of the Vermont Statutes names Guilford among Windham County’s towns and states that Newfane is the shire town. Newfane holds the county’s formal seat while Guilford holds the fair, and no fair-side layer credits Newfane or any county body with organising it. Newfane’s only fair-named contribution here is a separate, biennial history fair on its own common.

Quick Facts

Item	Detail
Event	Guilford Fair, a Labor Day-weekend agricultural fair
Host town	Guilford, Vermont
Shire town	Newfane, in Title 24, section 14 of the Vermont Statutes; it does not host
Organiser	Guilford Fair Association, the fairgrounds’ owner
Grounds	Fairground Road, off Weatherhead Hollow Road, in the fair’s own form
Standing days	Sunday and Monday of Labor Day weekend, in the vendor application’s form
2026 full days	September 6 and 7, 2026, gates at 7:00 a.m. in the homepage layer
2026 admission	Adults ten dollars, children 6 to 14 five dollars, seniors five dollars, cash only
Public camping	None offered in any fair-side layer

Eighty Years on Two Pieces of Land

The fair’s own homepage gives its beginning in one sentence: the Guilford Fair was first held on Labor Day, September 7, 1942, when work was set aside, neighbours caught up on the summer, and an annual tradition was born.

For a useful comparison, see the Rutland County Vermont Vermont State Fair Festival for another county festival.

The fuller sequence sits in the Official History of Guilford, Vermont, 1678–1961, a town-history layer. There the Association was organized on July 15, 1942, and the first fair has been held annually since with the exception of 1945. That exception stops the homepage’s annual-tradition wording from hardening into an unbroken-run claim. The same layer fixes the fair’s two homes: Evans land from 1942 through 1953, then Whittemore Park, acquired in 1954 from the late Bert A. Whittemore, the fair’s home since. Floral Hall was built in that first year on the new land. Fitch Hall, the exhibit building in the fair’s own 2026 homepage, is a different name in a different layer, never quietly swapped with it in either direction.

A Grange passage in the same history recalls exhibition interest reaching back to 1884, when the Grange exhibited farm products and handicrafts; that is precursor interest, never an 1884 founding. No Guilford-specific document for 2020 was found: a state layer records all Vermont fairs and festivals as announced cancelled that year, and the return is proven by a held edition on September 5, 2021 and a 2022 legislative listing. A 2021 visitor blog’s edition wording does not reconcile with the 1942 layers and is not printed here; nothing is ever worked backwards from it.

What to Expect

The Shape of the Weekend

The standing arrangement, in the fair’s own undated vendor application, is Labor Day weekend, Sunday and Monday, at 8:00 a.m. to 5:00 p.m. The fair’s own 2026 homepage adds a Saturday in front of those days without making it a third fair day: on Saturday, September 5, 2026, the grounds stood open 8:00 a.m. to 4:00 p.m. for picnicking with live music, exhibit registration running in Fitch Hall from 10:00 a.m. to 3:00 p.m. Sunday, September 6 and Monday, Labor Day, September 7 carried the full fair, gates at 7:00 a.m. in that homepage layer only.

Animals, Exhibits and Contest Tables

The fair’s own 2026 cattle form fences the Guilford Fair Open Cattle Show to Monday, September 7, 2026, starting at 10 a.m., open to all farms and breeds of cattle, with breed, herd, costume and steer and oxen classes; its late-entry figure of three dollars per animal is exhibitor money, nothing to do with the public gate. The King Arthur Baking Contest page for 2026 places entry drop-off on Saturday, September 5, 2026, between 10:00 a.m. and 3:00 p.m., names the Broad Brook Grange as administrator, and sets a youth contest for bakers up to seventeen, built around a Cinnamon-Crisp Coffee Cake, with gift-card prizes of forty, twenty-five and twenty-five dollars.

Rides, Music and Other Years’ Bills

Green Mountain Amusements supplies the rides in the 2026 record, the homepage fencing the unlimited-ride bracelet to one window: Sunday, September 6, 2026, 1:00 to 4:00 p.m., at twenty-five dollars each, midway money, never admission. Items appearing only in 2025 layers — a fair-side horse show form dated September 1, 2025, and listing mentions of a classic car show, an ox pull, farmer Olympics, a chicken barbecue, games and circus arts — stay in 2025, none asserted for 2026. A visitor’s 2021 observations — an obstacle-course practice, exhibition vegetables, a shearing demonstration, an oxen pull — likewise stay in 2021.

Planning Your Visit

Which Days, and When the Gates Open

Plan around Labor Day weekend’s Sunday and Monday, the 2026 days set out above. The other dated layers sit unmerged: August 31 and September 1, 2025 in the Agency of Agriculture’s list, listing-layer Saturday forms not extending those days; and a 2022 handout form standing in its layer only. Trust each year’s own record, never a blend.

Admission Is Cash, and Rides Are Separate

The only complete gate ladder on this record is the fair’s own 2026 homepage ladder: adults ten dollars; children six to fourteen, five dollars; five and under, free; senior citizens, five dollars. The same homepage calls it a cash only fair in its own wording. Carry gate money with you. The twenty-five dollar Sunday-afternoon bracelet sits on top of admission, never inside it. For 2025 the exact ladder is unverified fair-side; a news layer gives a range of five to ten dollars for Sunday, August 31, 2025 in that layer only. A 2021 visitor layer’s five-dollar senior figure is never dated forward, even though the 2026 senior price happens to match it. Vendor terms exempting a vendor and two assistants from admission are document terms, never a public offer.

Finding the Grounds

The fair’s own address form is short and unnumbered: Fairground Road, off Weatherhead Hollow Road, Guilford, VT, the association’s form adding the postcode as Fairground Road, Guilford, VT 05301. Listing layers print a numbered form, 163 Fairground Road, standing in those layers only, never merged into the fair’s own form. Two mailing addresses in the paperwork are not the fairgrounds: a Guilford mail-to address on Sweet Pond Road, and a cattle-form mail-to address on Sherwood Road in Aurora, New York, for posting entries to a person.

Parking and Sleeping Over

No parking price is published in any fair-side layer for any year, so every parking price for this fair is unverified. The vendor application requires vehicles outside a booth or demonstration to be moved to the parking area before gates open on fair days, proving a parking area exists in that layer; a 2021 visitor’s free parking in the fields is never a standing promise. Visitor camping is a documented absence on this record. The single overnight fact is fenced to the 2026 cattle form: exhibitors and cattle can arrive on the Sunday and spend the night, cattle supervised at all times, ahead of the Monday show. Scout troops camping on these grounds for a separate November 2026 event are a rental use, saying nothing about fair-week camping.

A Weekend on the Grounds

Treat Saturday as a gentle opening, not a fair day. In the 2026 pattern, entrants register exhibits in Fitch Hall between 10:00 a.m. and 3:00 p.m., bakers use the same window, and everyone else can picnic to live music until 4:00 p.m. Return early on Sunday, gates at 7:00 a.m. in the 2026 homepage layer, and give the morning to the barns. Keep Sunday afternoon for the ride-bracelet window, 1:00 to 4:00 p.m. Save Monday for the cattle show, starting at 10 a.m. in the 2026 form, and finish in the exhibit halls.

Namesakes and Near Misses

Comparisons here are mostly warnings. Connecticut’s Guilford Fair is a different fair in a different state, on its own September weekend; none of its dates, prices, parking, shuttle services, parade or circus acts belongs in Vermont, and Vermont’s 1942 beginning gains nothing from any Connecticut layer sharing a figure. Guilford, Maine’s fair survives in memory layers as a beloved event that ended; that ending is Maine’s story, never evidence about Vermont, whose record shows the opposite. Newfane’s biennial history fair is a real county event and still not this one, standing on Newfane’s common under its own name.

Before You Set Out

• Work from the fair’s own current homepage for the coming edition; older years’ dates are those years’ record only.
• Carry cash for admission: the fair’s own 2026 wording makes it a cash only fair.
• Budget the twenty-five dollar ride bracelet separately from the ten dollar adult gate.
• Navigate by the fair’s own address form, Fairground Road off Weatherhead Hollow Road; the numbered listing form is a listing layer, not the fair’s address.
• Register exhibits and baking entries inside the published Saturday windows, not on the full fair days.
• Assume no parking price and plan no camping: the price is unpublished, and visitor camping is not offered fair-side.
• Leave Newfane to its own history fair, and Connecticut’s Guilford Fair out of your directions, prices and expectations.

Beyond the Fairgrounds

Beside the fairgrounds sits a nine-acre recreation park off Weatherhead Hollow Road, owned and maintained by the Guilford Recreation Club in the town layer’s account; crossing into it means leaving the fair. Guilford itself, a hill town of farms and back roads, rewards the slow drive out, and Newfane keeps its own common and biennial history gathering.

Why This Fair Matters to Its Town

A fair organised in July 1942, in the middle of a war, was no entertainment venture; it was a town deciding to keep meeting. Its structure is unusually democratic: every Guilford citizen is a member of the Association that owns the grounds, in the town layer’s account. That ownership explains the character: the exhibit tables, cattle show and baking contest are the town showing its own work to itself. The record’s gaps suit that honesty: one clear cash ladder for the current edition, earlier years left in theirs.

Frequently Asked Questions

Is this fair the same event as the Guilford Fair in Connecticut?

No. This article covers the Guilford Fair at Guilford, Vermont, first held on Labor Day in 1942. Connecticut’s same-named fair is a separate event in another state, with its own history, grounds and prices; no fact from it is used here.

Who runs the Guilford Fair, and where exactly is it held?

The Guilford Fair Association runs it and owns the fairgrounds. The grounds stand on Fairground Road, off Weatherhead Hollow Road, in the fair’s own unnumbered form; a numbered form appears in listings only. Newfane is the county’s shire town and does not host.

What does admission cost, and can I camp at the fair?

For 2026 the homepage lists adults at ten dollars, children six to fourteen at five dollars, five and under free, and senior citizens at five dollars, cash only; the twenty-five dollar Sunday ride bracelet is separate ride money. The exact 2025 ladder is unverified fair-side, known only as a five-to-ten dollar range in a news layer. Visitor camping is not offered in any fair-side layer; the only overnight provision covers exhibitors and their cattle on the Sunday night before the 2026 cattle show.

Has the fair really run every year since 1942?

Not quite, and the fair’s own sources say so. The Official History records the fair held annually from 1942 with the exception of 1945, and nothing Guilford-specific covers 2020, a state layer recording Vermont fairs as cancelled that year; a held 2021 edition and a 2022 listing document the return. The honest claim is a long tradition with documented breaks.

What to Expect From the Next Windham County Vermont Guilford Fair Festival

How often is Windham County Vermont Guilford Fair Festival held?

Once a year, across Labor Day weekend: the fair’s own standing form gives that weekend’s Sunday and Monday as the fair days, and the record from 2022 through 2026 shows it returning each year.

When is the next Windham County Vermont Guilford Fair Festival?

None were published in any layer on this record. Expect the Sunday and Monday of the next Labor Day weekend at the Guilford fairgrounds, on the standing pattern, and confirm days and gate times in the fair’s own announcements before travelling.

Will the dates change?

They move with the calendar: Labor Day drifts between late August and early September, as the editions show — August 31 and September 1 in 2025 against September 6 and 7 in 2026. A three-day listing form survives for 2024 in its layer, so the shape around the two standing days can vary.

What endures is modest and deliberate: two days, one town, its own grounds and its own work on display. Arrive with cash and no borrowed facts from other Guilfords, and the fair will give you what its organisers promised in 1942: a day when work is set aside for a little while, and neighbours are glad of it.