The bulldog auction closed Friday night. Thirteen pumpkins are already standing in the village. The volunteer committee behind both projects is from Irvington, and this October its idea runs up and down the Rivertowns. That handoff matters more than any single event on the calendar this month. A group that started out decorating Main Street now sets the backdrop for the whole month, from the hayride to the parade.
How the Bulldogs Pay for the Pumpkins
Since May, artist-decorated fiberglass bulldogs have lined Main Street. Bidding on them closed at 8:00 PM on Friday, October 9, according to the Mayor's October 9 message. The Village counts 23 statues and the Bulldog Gallery's own 2026 page lists 24, so the exact number depends on which page you read. This year's themes ranged from an apple and a rockstar to a dragon, Batman, baseball players, constellations, the Phantom of the Opera and a cowboy. The apple was most likely Kristina Schmidt's "Applejack." Gloria Marrero's "The Pizza Man" was also in the catalog.
The auction money doesn't disappear into a general fund. The Mayor's September 30 message explained that proceeds are split between the artists and the Arts & Culture Committee. The committee uses its share to keep the Bulldog Gallery going and to pay for new projects, including the spring 2026 Pollinator Butterfly Planters and the Rivertowns Pumpkin Trail. So when the bulldogs come down, their sale helps pay for what goes up next.
The program is older than a lot of people assume. The Bulldog Gallery has run four summers in a row, 2023 through 2026. The committee itself started in 2022 with the goal of turning Main Street into a walking gallery. In 2024 it took on a broader mission, and the Village Board appointed it as the Irvington Arts and Culture Committee. In four years it has grown from a volunteer street-art project into an official village committee with a regular schedule: bulldogs in summer, butterflies in spring, and now pumpkins in fall.
The Trail That Left Town
The Rivertowns Pumpkin Trail is new this year. It runs October 1 through November 1 across six villages: Ardsley, Irvington, Dobbs Ferry, Sleepy Hollow, Hastings-on-Hudson and Tarrytown. The trail's Irvington page says where it came from:
"Irvington Arts & Culture Chairperson Kristina Schmidt, founder of the Rivertown Pumpkin Trail, created the trail following the success of Irvington's Bulldog Galleries and Butterfly Gallery & Pollinator Gardens."
The other villages put their own groups behind their sections. In Sleepy Hollow, for example, the Village credits its Pumpkin Gallery to the Sleepy Hollow Art & Placemaking Committee and the Friends of Sleepy Hollow. Each village runs its own part, but the format was developed on Irvington's Main Street. If friends in Dobbs Ferry or Hastings are out pumpkin hunting this month, they're following a model Irvington tested first.
Where Irvington's 13 Pumpkins Stand
Irvington has 13 original pumpkin sculptures around the village, each one made by a local artist. The Irvington gallery guide includes a map and a Google "Pumpkin Finder." Several pumpkins sit right on routes you probably take for errands anyway:
| Pumpkin | Artist | Location |
|---|---|---|
| Great Pumpkin | Natalia Schmidt | 1 North Broadway |
| Enchanted Coach | Kristina Schmidt | Village Hall, 85 Main Street |
| The 13th Hour | Kristina Schmidt | Village Hall, 85 Main Street |
| Kussa | Abi Brandwein | Irvington Train Station, Astor Place and Main Street |
The other nine are Laura Saracino's "Harvest," Gloria Marerro's "Guardian of Wisdom," Arielle Royston's "Gem O'Lantern," Enissa Acevedo's "Gorgeous Gothic," Kristin Mann's "iSpy Halloween," Joana Ricou's "Goblins, Bats, Oh My," Zadie Bloom's "Coraline," Jessica Pickens' "Behind Every Door" and Al Villacara's "Palisades Sunset." Their spots are on the map.
Many of the bulldog artists came back for the pumpkins. One returning artist has been in all four Bulldog Galleries and has a hand in two pumpkins this fall. Kristina Schmidt chairs the committee, made "Applejack" for the bulldog show, and has two pumpkins outside Village Hall. The same local artists show up season after season.
A practical route: start at the station at Astor Place, walk up Main Street to Village Hall at number 85, and finish at 1 North Broadway. That covers four of the 13 pumpkins in one stretch. Bliss Bakehouse, which opened on Main Street in May, is along the way if you want a snack.
The Same Streets, Busier Weekends
The pumpkins stay up through every event on the village calendar this month. Here's how the month lines up, based on the Parks and Recreation Community Special Events listing and the Mayor's messages.
- Saturday, October 17, Harvest Hayride. Runs 6:00 to 8:30 PM in Matthiessen Park. It turns haunted at 7:00 PM and the line closes promptly at 8:15. Jake's Rockin' Country Band is playing and the Irvington High School Midnight Run is holding a bake sale. Parks and Recreation asks that dogs stay home. The event is free. Lyndhurst's Trick-or-Treat Weekend is October 17 and 18, so families who want a full Saturday of Halloween can plan around both.
- Friday, October 23, "Enlightenment" at the Irvington Theater. The American Classical Orchestra plays Mozart's Clarinet Quintet and Haydn's "The Joke" at 7:30 PM. Lyndhurst's Gothic Market Weekend also starts that day and runs through October 25.
- Saturday, October 24, Window Painting. It's on the Parks and Recreation calendar for the day before the parade.
- Sunday, October 25, Halloween Parade. The free parade starts at 3:00 PM, hosted by Irvington Parks and Recreation and the Irvington Fire Company. The Mayor's September 30 message labels this date a Saturday, but October 25, 2026 is a Sunday. The Parks and Recreation listing from August 19 gives Sunday, October 25, and that's the date to put on your calendar. The same morning, the O'Hara Nature Center hosts the Living Forest Speaker Series talk "Growing Mushrooms, Growing Forests with Connor Youngerman" from 10:30 AM to 2:30 PM. October 25 is also one of the Irvington Farmers Market dates on the Visit Sleepy Hollow calendar.
- Friday, October 30, "Ghost Light." A multidisciplinary Halloween performance at the Irvington Theater, 7:30 PM.
- Sunday, November 1, the trail's last day. The Pumpkin Trail closes, Lyndhurst's Daily Grounds Pass season ends, and the farmers market has its last listed date. The November 1 market date is the latest one listed. No official season end has been announced.
The busiest stretch is October 23 through 25: a concert, the window painting and the parade in Irvington, with the Gothic Market going on at Lyndhurst all three days. Rocktoberfest, which was scheduled for September 26, was cancelled this year. That makes the hayride the first big Parks and Recreation evening of the fall.
Before Parade Day
On October 8, the Village posted a Halloween map with road closures, detours and parking information. The map is posted only as images, so open it yourself before you drive or park downtown that weekend.
If you're catching up on the season, the Irvington Theater's Good Company Fall Benefit Concert on Saturday, November 7 at 7:30 PM is next. It features Broadway performers with Good Company's adult and youth troupes. The theater hasn't posted December programming yet.
The pumpkins stay up through November 1. After that the committee moves on to its next season, presumably paid for, in part, by what the bulldogs earned.
I love seeing Irvington's volunteers and local artists set the tone on Main Street every season, and I know how much curb appeal and walkability factor into what homes here are worth. If you live near the pumpkin trail and want to know where your home stands this fall, reach out to Elka Raved and Get an Instant Home Valuation.
