In 2017, Hannah Small was baking out of Cask & Kiln, and that work got her a commercial bakery license. A year later she tied for first place in Wilmington's first Make It On Main Street business plan contest and used the money to renovate space in the Old School Community Center. Butter Mountain Bakery opened there in fall 2019 with "a line out the door," as Small told the Bennington Banner.
Seven years on, her sourdough is sold at Mill & Whistle, the café at 24 West Main Street. That building is the one a different contest winner planned to reopen in 2025. Under Wilmington Works, the contest has funded three rounds, and the third round's finalists were set to present on Friday, October 16, 2026. The earlier rounds are already visible on a short walk through the village. Most of the money has gone to people who were already working in Wilmington, and their businesses have ended up selling to one another.
The Bakery That Won Twice
The 2025 round was the second time Small took the top prize. At the February 20, 2025 final at Arthouse, she won $50,000 to hire her first employee and buy a proper bread oven. She told the Bennington Banner that she wanted to become Southern Vermont's artisan sourdough supplier. "The problem is," she said, "I can't keep up with the demand, and there is a lot of it."
Her expansion drew on more than one source of money. A June 2026 profile from NOFA-VT credits an infrastructure grant with helping her buy equipment, move into a larger space and start adding staff. Wilmington Works' May 2026 announcement in the Deerfield Valley News says the contest also "received support for the expansion of the business."
You can taste the scale-up well beyond Wilmington. By spring 2026, Butter Mountain was baking whole-wheat sourdough rolls for Brattleboro schools. For one meal service Small delivered 1,200 rolls, and NOFA-VT reported that every one was eaten. The partnership planned to serve the rolls monthly. When she started in 2015, she was selling baked goods and farm produce from a single table at the Whitingham Farmers Market.
In Wilmington, buying from her still runs on her own schedule. The Butter Mountain website posts a weekly online menu for Friday pickup and lists Friday walk-in hours from noon to 5 p.m. The same site lists five wholesale outlets: Farmhouse Market, River Valley Market, West Wardsboro Store, River Bend Market and Mill & Whistle. If Friday doesn't fit your week, the last name on that list is your easiest option.
The Yellow Building on West Main
That last name brings in a second contest story. In February 2025, a project called Local Loop won $45,000 with a plan for 24 West Main Street. That's the yellow building across from the Southern Vermont Deerfield Valley Chamber of Commerce office, and the Bennington Banner reported it had sat empty for about seven years. The plan was a shared retail hub with food and drinks, embroidery and labeling services, and a ghost kitchen for rent.
The building is now Mill & Whistle, a café and market owned by Drew and Liz Christo, with Michael Moreno as executive chef. The Deerfield Valley News reported in January 2026 that it was open and serving breakfast seven days a week from 6 a.m. Mill & Whistle's website lists breakfast, baked goods and lunch, along with shelves of pantry items, snacks and home goods. It also takes online orders for drive-through pickup.
So the 2025 winners' plans and the street's current owners have merged in practice. The contest picked a building that had sat empty for years and called attention to it. A café now fills it, and that café sells bread from the contest's two-time winner. Anyone coming down Route 9 before 7 a.m. now has a place on West Main to stop for coffee.
Where Each 2025 Finalist Stands
Four finalists made it to the stage at Arthouse in February 2025, out of 26 applicants. Here's where their pitches stand going into November 2026.
| Finalist | 2025 pitch | Award | On the ground in fall 2026 |
|---|---|---|---|
| Butter Mountain Bakery | Bread oven, first employee | $50,000 | Friday pickup and walk-ins; wholesale in five stores; Brattleboro school rolls |
| Local Loop | Shared retail hub at 24 West Main | $45,000 | Address now home to Mill & Whistle, owned by Drew and Liz Christo |
| Cherry Press Printmaking | Print studio at Arthouse | $15,000 | Marked its first anniversary in May 2026; November classes listed |
| Valley Craft Ales | Brewhouse on North Street property | None | Beer, pizza, lodging and events on North Street |
A Printer Where Wilmington Asked for One
Corinne Rhodes also teaches printmaking at Bennington College. She won $15,000 to lease part of Arthouse on South Main Street for screen printing, silkscreen and lithography. "I've heard from various people that Wilmington needs a printer," she told the Bennington Banner. Cherry Press held its ribbon cutting and grand opening on Saturday, May 24. In May 2026, the Deerfield Valley News reported that Cherry Press was celebrating its first anniversary. Wilmington Works lists the studio at 12 South Main Street.
The fall class schedule has two November dates left.
- Intro to Letterpress, Sunday, November 8: setting type by hand and printing a single color.
- Woodcut Printing, Sunday, November 22, 1 to 4:30 p.m.: carving a block and printing it.
Cherry Press is the 2025 winner that most fits the original idea of bringing something new to town. Even so, it went into Arthouse, an existing arts building that was also the contest's stage. Two of the four 2025 finalists, Butter Mountain and Valley Craft Ales, were already running businesses in Wilmington when they pitched.
The Finalist Still Working on Its Plan
Valley Craft Ales was the fourth finalist and the one that came away without an award. Co-owner Chrystal Holt pitched a brewhouse in an unused building on the company's North Street property, the former Old Red Mill Inn. According to the Bennington Banner, the beer was then brewed under contract in New York, which raised costs. The project was estimated at about $205,000, and Holt said VCA would "continue to brainstorm on ways to fund the project and bring brewing onsite." Valley Craft Ales' website still promotes beer, pizza, lodging and events on North Street.
Its pitch shows how far a single prize can go. The 2025 pot reached $110,000 across three winners. The fund started at up to $75,000, then Wilmington Works added $20,000 and an anonymous donor gave another $20,000. Volume III offers one prize of $40,000 "to support the opening of the business." That's less than a fifth of the brewhouse estimate.
What Round Three Is Asking For
The money behind the contest is local too. The Deerfield Valley News announcement credits Paul Pabst, a longtime Deerfield Valley second-home owner, with first inspiring the contest. Dan Kilmurray sent the remaining Wilmington Fund money to Wilmington Works, which let the contest return in 2024 and again in 2026. Local businesses and organizations added sponsorships.
The Volume III rules ask entrants to show how they would serve locals, second-home owners and seasonal visitors. Wilmington Works says it particularly encourages businesses that create steady jobs and diversify the local economy. According to the same announcement, both 2018 winners, Butter Mountain Bakery and 802 Fitness, are still in business. Rules and updates are posted at Wilmington Works.
The Main Street Businesses Not in the Contest
Not every change on Main Street goes through a contest. At 30 West Main Street, Steve Butler has owned North Star Pizza & Bowling since 1979. He listed the business for sale in January 2026, and the Deerfield Valley News reported in April that it hadn't sold yet and that he was ready to hand it to whoever takes it into its next chapter. Whoever buys it will take over a 47-year business with a pizza kitchen and bowling lanes on West Main Street.
The village calendar runs on familiar dates in the meantime. Wilmington Works lists downtown trick-or-treating on Main Street this Saturday, October 31, from 4 to 6:30 p.m., along with a jack-o'-lantern display at River Bank Park. On Thursday, December 10, Memorial Hall hosts its holiday concert. A variety show starts at 5 p.m., the tree and menorah lighting with cocoa follows at 6 p.m., and the concert begins at 7 p.m.
Wilmington Works will announce the Volume III winner, and one more storefront will change. Flex Realty works from West Dover, just up Route 100, and follows these Main Street changes because they shape the town our clients live in. If you're thinking about what a new business, a sale or an empty building on your block means for your own property, contact us. We'll give you a clear, local answer.
