The Village canceled Rocktoberfest, which had been set for Saturday, September 26. That leaves early October in Irvington with no anchor event. Main Street fills the gap. This month the village's public art runs the full length of the street, from North Broadway down past Village Hall to the train station. The Greater Irvington Land Trust holds its Open Space Heroes celebration at the O'Hara Nature Center on October 4. Beyond that, the Village's dated events wait until the second half of the month, and the biggest of them happens at the river end of that walk.
That makes October unusual for Irvington. In most months you go to an event and walk past the street. This month the street is the event, and the calendar comes later.
Thirteen Pumpkins, Numbered Down the Hill
The Rivertowns Pumpkin Trail is new this year. It is a regional public art exhibition where local artists turn large decorative pumpkins into one-of-a-kind pieces. Irvington's part of it is 13 original sculptures placed around the village. Kristina Schmidt, who chairs Irvington Arts & Culture, founded the trail after the success of the Bulldog Gallery and the Butterfly Gallery & Pollinator Gardens. Six villages take part: Ardsley, Dobbs Ferry, Hastings-on-Hudson, Irvington, Sleepy Hollow and Tarrytown.
Irvington's placements line up almost entirely along one route. Start at the top and the street numbers count down as you walk toward the Hudson:
- 1 North Broadway. "Great Pumpkin," by Abi Brandwein and Natalia Schmidt, starts the trail at the top of the hill. Natalia dedicated it to her late grandfather, who watched the Charlie Brown holiday special with the family every holiday.
- 136 Main Street. "Harvest," by Laura Saracino, a self-taught painter. A recent trip to Montana inspired it: wide skies, mountains and a harvest moon.
- 110 Main Street, where Main crosses the Aqueduct Trail. "Guardian of Wisdom," by Gloria Marrero. She is an Irvington artist and the owner of Penny's Party Place, and she has also worked on the village's Butterfly, Mural and Bulldog projects.
- 107 Main Street.
- 85 Main Street. Two works stand at Village Hall.
- 78, 71, 48, 35 and 18 Main Street. One sculpture at each address on the lower blocks.
- Irvington Train Station at Astor Place and Main Street, then 1 Bridge Street, across from the station by MP Taverna.
The Aqueduct Trail stop at 110 Main Street matters for anyone who walks the trail. If you cross Main Street on the Old Croton Aqueduct this month, you will pass a pumpkin without leaving your usual route. The trail's Irvington page has a gallery guide and a Google map you can save to your phone. Each entry gives the artist's background and the idea behind the piece.
Sources disagree about when the trail opened. The Village of Sleepy Hollow's calendar lists both September 20 and October 1 as start dates, but both entries agree it runs through November 1. In her September 30 message, Mayor Arlene Burgos said the trail was launching that week. If you count from the first week of October, you have about four weeks to see it.
Through October 9, the Bulldogs Share the Sidewalk
For the first part of the month, the pumpkins share Main Street with a show that is still up. The 23 fiberglass bulldogs that have lined the street since May are being auctioned now. Artists decorated them with an apple, a rockstar, a dragon, Batman, baseball players, constellations, the Phantom of the Opera, a cowboy and more. Bidding runs through Friday, October 9, at 8:00 p.m. at bulldoggallery.org.
The two shows share a budget as well as a sidewalk. Bulldog auction proceeds are split between the artists and the Arts & Culture Committee. The committee's share pays for the next projects, which have included the spring 2026 Pollinator Butterfly Planters and the Rivertowns Pumpkin Trail itself. The pumpkins will follow the same model. Greenburgh's announcement of the trail says each pumpkin will be auctioned after its display, with 30% going to the artist and the rest supporting future public art. A bulldog bought this week helps pay for whatever lines Main Street next year.
The purple glow on the clock tower is a separate thing. The Village is lighting it purple from October 1 through 11 for Domestic Violence Awareness Month.
The River End Takes Over After the Seventeenth
The month's first big gathering is at the bottom of the hill. The Harvest Hayride takes over Matthiessen Park on Saturday, October 17, from 6:00 to 8:30 p.m. The ride turns haunted at 7:00, and the line closes promptly at 8:15. Jake's Rockin' Country Band plays, and Irvington High School Midnight Run runs a bake sale. The hayride is free.
The Village asks that dogs stay home that night. Dog owners should know that this request is new against a backdrop of new access nearby. Since September 14, leashed dogs have been allowed on the paths in Scenic Hudson Park. The rules call for a valid license and current vaccinations, a leash no longer than six feet, no more than two dogs per handler, and staying on the designated paths. Dogs are still not allowed on the ballfields or playgrounds, in the restrooms, at the Senior Center or at the 9/11 Monument. This is the first October that a riverside dog walk in Scenic Hudson Park is allowed. The one evening the Village asks owners to leave dogs at home is hayride night at Matthiessen.
The Late-October Calendar
After the hayride, the dated events come close together. Most fall in the last nine days of the month:
- Friday, October 23, 7:30 p.m. The American Classical Orchestra performs "Enlightenment" at Irvington Theater, including Mozart's Clarinet Quintet and Haydn's "The Joke."
- Saturday, October 24. Window Painting.
- Sunday, October 25, 10:30 a.m. to 2:30 p.m. Connor Youngerman of the Cornell Small Farms Program leads "Growing Mushrooms, Growing Forests" at the O'Hara Nature Center. The hands-on session covers backyard mushroom growing and air-pruning techniques for native trees and shrubs.
- Sunday, October 25, 3:00 p.m. The free Halloween Parade, hosted by the Irvington Parks and Recreation Department and the Irvington Fire Company. Costumes encouraged.
- Friday, October 30, 7:30 p.m. "Ghost Light: A Haunted Evening of Music, Movement, Poetry & Film" at Irvington Theater. Performers include Rivers Edge Theater Company, Hudson Valley Arts Collective, soprano Ruby Nightingale, and dancers Erica Moshman and Sydney Rosenburg, along with short films.
- Sunday, November 1. The last day of the Rivertowns Pumpkin Trail.
October 25 is the busiest day. You could go to the mushroom program in the morning and still make the 3:00 parade. The Village's September 30 message lists the parade as a Saturday, but its August events list gives Sunday, October 25, which matches the calendar.
The mushroom program is the one stop off the Main Street route. The O'Hara Nature Center is at 170 Mountain Road. It is part of the Living Forest Speaker Series, a set of free programs on forest stewardship, restoration and biodiversity run by the Irvington Green Team and the nature center. Registration is requested.
The two theater nights keep you downtown. Irvington Theater is on the third floor of Town Hall downtown. On October 23 and 30, the Main Street pumpkins are still on display.
The Week the Trail Comes Down
The month ends with a practical errand. On November 1, the Pumpkin Trail's last day, Irvington Hardware begins selling the designated 5-gallon sealable bins for the Village's new food-scraps program. The bins cost $20, and residents must buy one to take part. Opt-in curbside collection for single-family homes starts Friday, January 8, 2027. Enrollment details are on the Irvington Green Team website. The Village says the service builds on more than eight years of community composting in Irvington. If you are walking Main Street on November 1 to catch the last pumpkins, the bin is something you can pick up on the same trip.
If you are thinking about a home within walking distance of Main Street, or you want to understand what this stretch of Irvington adds to a property you already own, Andrea Weiss can walk you through it. Work With Andrea.
