If you've lived in Westport long enough to have a stack of those hand-drawn Harvest Festival posters somewhere in a closet, cows and pumpkins and hidden quahogs pressed into the design, you might have done a double take at this week's signs for the South Coast Harvest Festival. Same words, same general season, same fairground energy. It feels like it should be the same event picking up where it left off.
It isn't. The festival opening at the Westport Fairgrounds this Friday shares a name with something Westport used to have, and almost nothing else. Understanding the difference tells you something real about how this town keeps its traditions alive, and how easily a name outlives the thing it originally described.
This Weekend, In Specifics
The South Coast Harvest Festival runs Friday, September 25 through Sunday, September 27 at the Westport Fairgrounds on Pine Hill Road. Friday hours are 3 to 8 p.m., Saturday runs 10 a.m. to 8 p.m., and Sunday wraps at 6 p.m. Admission is cash only at the gate, $10 for adults and $5 for children ages 5 to 12, with kids under 5 getting in free. Parking is free.
This is the festival's fourth year, and organizers have added a Paul Bunyan Lumberjack Show to the lineup this time, with chopping, sawing, axe throwing and log rolling on the fairground track. The rest of the bill will feel familiar if you went last year: Chrissy Joy and The Joy Crew doing their stunt dog act, professional pumpkin carver Richard Kaiser at work in real time, live owl presentations from Eyes on Owls, the Toe Jam Puppet Band, and a marketplace of roughly seventy artisan vendors. Local landscapers and garden designers build out show gardens across the grounds, lit at night, which has become one of the event's signature visuals.
None of this existed before 2023. The South Coast Harvest Festival was built from scratch by Michelle Sousa Peay and her husband Brian Peay, who launched it as a privately funded event and initially priced tickets high enough to draw complaints from families in town. They cut prices roughly in half the following year and have kept expanding the production since, adding acts, vendors and now a full lumberjack competition. It is, by design, a commercial entertainment event that happens to be seasonal and outdoors. There is nothing wrong with that. It just isn't what the name used to mean here.
The Festival That Came Before It
Westport had its own Harvest Festival long before this one, and it ran on a completely different premise. Through the 1990s and into the early 2000s, the town held an annual Westport Harvest Festival built around farming, fishing, open space and the environment, explicitly framed as a way of celebrating and supporting the human and natural resources of the town. The Westport Historical Society still holds a collection of commemorative posters from those years, one for each edition, each one packed with hidden details a viewer had to hunt for: pumpkins worked into stone walls, a quahog and a lobster hidden in a cow's silhouette, the festival's founding date tucked into a cloud shaped like a bunch of grapes. The twelfth and final poster on record is dated 2003.
Bob and Carol Russell, who founded Westport Rivers Vineyard on Hixbridge Road, were the ones who pulled the original festival together, drawing in local teachers, artists and farmers to help run it. One of those artists, a chemistry teacher at Westport High School named Betsey, recalled that back then the town still had eleven working dairy farms, and that students would finish barn chores before heading to class. That festival wasn't selling tickets to watch a lumberjack show. It was a working farm town publicly reminding itself what it was.
Twenty Years Between Them
The original festival appears to have quietly stopped sometime after 2003. Westport kept farming, kept its coastline, kept its conservation land, but it went two decades without an autumn event carrying that name at any real scale. The Westport Land Conservation Trust and the Trustees still hold a smaller-scale Harvest Festival gathering at the Westport Town Farm most years, closer in spirit to the original than to what's happening at the fairgrounds this weekend, but it has never approached the size or visibility of the new event.
That gap matters. When the South Coast Harvest Festival launched in 2023, it wasn't reviving anything. It was filling an empty calendar slot with a new idea that happened to reach for a name Westport already associated with autumn. The overlap in language created an overlap in memory that the facts don't actually support.
The Anniversary Nobody Put on a Sign
While the fairgrounds were building toward a fourth annual festival with a new lumberjack act, Westport Rivers Vineyard quietly marked forty years in business on September 10. Bob and Carol Russell bought the 110-acre Long Acre Farm in 1982, land that had been slated for fifty house lots before they got there instead. They planted 44,000 vines in 1986, released their first wines in 1991, and the operation has since grown to roughly 85,000 vines and about 10,000 cases a year, still run by the same family. Their son Rob now oversees the vineyard, winery and brewery, with a third generation of Russells starting to take on roles across the business.
Carol Russell has said that falling for the operation meant falling for the town first. "We also fell in love with the town," she said, describing an agricultural and fishing community that matched what they were looking for in a home for the vineyard. Over four decades, the family has helped put close to 500 acres of Westport land into conservation and helped establish the Coastal Growers Association alongside the original Harvest Festival. There was no ticketed weekend built around the anniversary, no lumberjacks, no illuminated show gardens. It surfaced mostly in a single newspaper feature.
That contrast is the whole story in miniature. One of these harvest traditions is a for-profit weekend production entering its fourth year and still finding its footing on pricing and scale. The other is a forty-year family farm milestone that barely made a ripple outside a local paper, despite having actually shaped the town's conservation map and started the tradition everyone now associates with the wrong event.
What's Actually New This Weekend
If you're headed to the fairgrounds, here's what wasn't there last year:
- The Paul Bunyan Lumberjack Show, featuring chopping, sawing, axe throwing and log rolling competitions
- An expanded artisan marketplace, now drawing close to seventy vendors
- Nightly illumination of the professional garden displays, a feature organizers have leaned into as the event has grown
None of it is a bad way to spend a fall afternoon. It's just worth knowing what you're watching, and what it isn't.
What the Overlap Actually Tells You
Westport hasn't lost its harvest tradition so much as split it in two. The instinct that built the original festival, farmers and fishermen and conservationists publicly marking the town's working land, still exists. It shows up in the acreage the Russell family has protected, in the smaller land trust gathering at the Town Farm, in the fact that Westport Rivers is still family-run four decades in. Meanwhile, a separate and much younger tradition has grown up around a similar name, built by different people for a different purpose, and it's the one getting bigger and louder every September.
Both are worth your weekend. Just don't expect the lumberjack show to explain why the vineyard down Hixbridge Road put five hundred acres into conservation. That story predates the fairgrounds event by twenty years, and it never needed a ticket price to matter.
If you're weighing what a town like this actually offers beyond the festival calendar, from working farmland to protected coastline to the kind of neighbors who'll tell you the real history behind an event's name, Cherry Arnold has spent years learning the Farm Coast at exactly this level of detail. Schedule a private consultation whenever you're ready to talk about what living here really looks like, in every season.
