Rutland Herald Best of the Best: How Voting Works & How to Win

A Rutland County ballot, not a statewide one

Ten towns feed this ballot, and most Rutland County voters think in terms of their town first, the county second. Rutland Herald Best of the Best runs across Rutland (city), Rutland Town, Castleton, Fair Haven, Poultney, Brandon, Pittsford, West Rutland, Proctor, and Killington, real communities with different customer bases, not contest subdivisions someone invented for the ballot. A Proctor marble-town retailer and a Killington resort restaurant are technically on the same ballot. Practically, they are fishing in different ponds entirely.

The Rutland Herald, part of New England Newspapers (vtcng.com), runs the contest on the SecondStreet platform at rutlandherald.secondstreetapp.com. It has gone annually since at least 2021, with confirmed cycles in 2021, 2023, 2024, and 2025. Over 100 categories span restaurants, dental, auto, home services, contractors, and media personalities.

For the full slate of Vermont contests we track, see the Vermont contest hub, or the nationwide USA contest index for a same-format program in another state.

What the Darren Perron result actually tells you

One name survives from the public record in enough detail to cite: WCAX's Darren Perron, Best TV Personality, 2025. That is not a coincidence of category. A television anchor arrives at the ballot with an existing audience, built over years of nightly air time, and that audience needs no introduction to who they are voting for.

A restaurant or a dental office starts from zero name recognition outside its existing customers. So the real lesson from the Perron win isn't "media personalities win." It's that pre-built audience reach, whatever its source, still counts for more than last-minute hustle. A Rutland auto shop with a loyal 15-year customer base is closer to Perron's position than it might assume; a brand-new Castleton café is not.

Beyond Perron, the Herald does not publish a full winners archive here. Category breakdowns, vote totals, and runner-up margins live behind the SecondStreet results page for each closed cycle. Check rutlandherald.secondstreetapp.com directly rather than trusting a secondhand list.

Category structure decides more than most businesses assume

This isn't one popularity contest with 100 names on it. It's 100-plus separate lanes, and choosing the wrong one costs a business real votes before a single supporter clicks anything. Restaurants, dental, auto, home services, contractors, media: pick the lane where an existing customer recognizes the business on sight, not the one that sounds the most flattering.

For category-specific playbooks beyond this page: a restaurant owner benefits from the restaurant vote-drive guide, a media-personality entry from the on-air personality promotion notes, and any category from the broader business award voting framework. None of these replace checking the live ballot for the exact current category label.

The calendar problem nobody solves in advance

Four confirmed cycles (2021, 2023, 2024, 2025), and not one published a locked opening or closing date ahead of time. That's the operating reality. A business that books print ads or orders QR table cards against a guessed deadline risks printing the wrong date entirely.

No cap being published is not the same as no rule existing. Read the live ballot every cycle. Don't assume 2025's repeat-vote allowance survives to the next one.

Why West Rutland and Killington need opposite campaigns

West Rutland is small and stable. Most of its realistic customer base already knows the business by name, so a counter mention or a single staff script at checkout covers the available pool within days. Killington runs on the opposite clock: seasonal, transient, resort-driven. A lodge or restaurant there gets more mileage from emailing last winter's guest list and posting a QR code at the front desk than from counting on foot traffic that may not be Rutland County residents at all.

Proctor carries a marble-heritage identity that still shows up in local pride messaging. Castleton skews toward college-adjacent retail and food, meaning a campus-calendar-aware push (students plus staff, not just year-round residents) reaches further than a generic county-wide post. Rutland city itself is the largest pool and the most category-diverse. Restaurants, dental, auto, home services, and media audiences all overlap there, so category clarity matters more in the city than anywhere else on this ballot.

None of these ten towns are official contest divisions. They're where the actual voters live, and a campaign built around the wrong one wastes effort on people who were never going to see the ask.

Running an outreach campaign without creating a compliance problem

Anchor every decision to whatever rule sits on the live ballot that cycle, not to what a business did two years ago. Real customer lists, staff scripts, receipt QR codes, and dated social posts work. Fake accounts, scripted voting, and "winner" language before results post do not, and they cost more in reputation than they add in raw votes for a business whose name is attached to the community it serves.

The Enhanced Listing option ($100 per category) is a visibility upgrade on the ballot page. It sits apart from the vote itself and should be treated as one, not marketed as a way to move numbers. Businesses layering paid promotion on top of a genuine local base see it work as intended: reach, not replacement, for real supporters. See real votes guidance for the broader standard, the county-wide framework at award-voting guide for cross-contest comparison, and how paid vote support works generally if this is your first readers-choice campaign. Businesses running a companion social push often pair this with Facebook-based reminders for the same customer list.