At 1:35 p.m. on Saturday, October 17, the oyster shucking and eating contests begin on the Main Stage at Theodore Roosevelt Memorial Park. Organizers expect to sell more than 70,000 oysters from Long Island waters over the weekend, served raw on the half shell, grilled, fried and Rockefeller style. About an hour earlier, up Planting Fields Road, Planting Fields Foundation's guests will gather at 12:30 p.m. for the ribbon cutting on the first garden Piet Oudolf has designed for a public site on Long Island.
For 42 years, October in Oyster Bay has mostly meant one weekend. This year the town's biggest crowd shares its Saturday with a garden that opens partly planted and keeps filling in through November. The 43rd Oyster Fest is still a two-day event. The Oudolf Garden is the start of a longer season, and the full calendar now runs from October 10 to November 22.
The Harbor Gets Two Days
The 43rd Oyster Fest is a partnership between the Town of Oyster Bay and the Oyster Bay-East Norwich Chamber of Commerce. The LI Herald reports it is expected to draw hundreds of thousands of visitors to Theodore Roosevelt Memorial Park and Audrey Avenue. Newsday lists the hours as 11 a.m. to 6 p.m. both days, with free admission.
The waterfront Main Stage lineup on Saturday is KAMELLOT, That 70's Band, Simply Stapleton, Echoes of the Eagles and Crash My Party. Sunday brings Ready in Ten, Vinyl Revival, Diva and the Bar Band Heroes, Glass Houses and Radio Flashback. Audrey Avenue has its own stage of local and regional acts, including Al Smith, Ape Theory, Juice, Chris Ruben Band, Dysfunktone and Miss J Experience on Saturday, and Ariana Chetram, Crisis and Rob Eberle on Sunday. The Oyster Bay Brewing Company Beer Garden overlooks the harbor and is limited to guests 21 and older. The Newton Shows carnival handles rides and games, and West End Avenue hosts a U.S. Army climbing wall and a New York Islanders slap shot attraction.
Some of the oyster shells will go back into the water. The Town is recruiting shell-recycling volunteers for three-hour shifts between 10 a.m. and 7 p.m. on both days, which is about as close to the harbor end of the festival as a resident can get.
Parking near the park is limited. The Long Island Press reports free shuttle buses running from designated lots at Syosset Rail Station and James H. Vernon School. According to the Herald, shuttles run from 11 a.m. to 6:30 p.m., half an hour past the festival's close.
| Getting in and out | Details for October 17–18 |
|---|---|
| Shuttle lots | Syosset Rail Station; James H. Vernon School |
| Shuttle hours | 11 a.m. to 6:30 p.m., Saturday and Sunday |
| LIRR | Extra trains on the Port Jefferson and Oyster Bay branches |
| Penn Station to Oyster Bay | Departs 10:17 a.m., 12:17, 2:14 and 4:17 p.m.; arrives 11:43 a.m., 1:43, 3:43 and 5:43 p.m. |
| Oyster Bay to Penn Station | Departs 12:37, 2:37 and 4:37 p.m.; arrives 2, 4 and 6 p.m. |
The train times come from the MTA's regular Oyster Bay Branch weekend timetable, which is in effect from September 8 through November 8, 2026. The added festival trains are not labeled in it, so friends coming out from the city should check the MTA before they leave.
The Garden Gets the Whole Fall
Planting Fields Foundation describes the Oudolf Garden as the most significant addition to the 409-acre estate since the Olmsted Brothers finished their work in the 1930s. It is also Oudolf's first public garden in New York in more than a decade, following the High Line and Battery Park. The opening date has held since the spring. A June LI Herald report set the public opening for October 17, and a July 21 New York State tourism release gave the same date.
Side of Culture walked the site in late August with Dr. Gina Wouters, the foundation's president and CEO. The one-acre garden sits near the Main House, enclosed by tall trees and an existing hedge, and the historic rose arbor runs through the middle of it. Pea-gravel paths and curving wooden benches separate the planting areas. Prairie dropseed anchors central meadows built on slightly raised ground where visitors can sit. Seasonal perennials fill the north and south sides, and 60 percent of them are native. In August that meant yellow yarrow and purple Stoke's asters among the grasses. No one has yet published a description of the garden in October.
The detail that matters most for local timing is in the same report. The garden holds 25,000 plants and grasses from more than 100 species, and its 22,000 bulbs are scheduled to go in during November. Whatever is there on opening day is the first version of a garden designed to change through all four seasons. A visit in late October, and another next spring, will show it at different stages.
Two details about the Saturday itself. The foundation's October 17 event, which pairs the garden unveiling with the opening of Dutch artist Fiona Tan's Catalyst 2026 installation, is free but invitation-only for donors and volunteers. RSVPs are due Friday, October 9. The foundation's listing does not say how general visitors can reach the garden while the ceremony is underway. Planting Fields is open every day from 9 a.m. to 5 p.m. The grounds are free, and an $8-per-car parking fee is collected on weekends and holidays from Labor Day through November 16, so it applies on festival weekend.
How the Two Clocks Fit Together
Since the festival lasts two days and the garden stays open all fall, a local's weekend can be planned in this order:
- Saturday, October 17. Go to the harbor. The shucking and eating contests are only on Saturday's Main Stage, and the shuttles from Syosset and Vernon School begin at 11 a.m.
- Sunday, October 18. If you're going back to the festival, Sunday's Main Stage switches to Glass Houses, Radio Flashback and the rest of the second-day lineup. The garden is open from 9 a.m. if you would rather visit on a quieter day than Saturday.
- Saturday, October 24. This is the busiest single day on the fall calendar, as the next section shows. The garden will have been open a week by then, and the bulbs are still ahead.
October 24 is crowded because both institutions schedule their own fall events around the festival. Planting Fields holds its annual Fall 5K/Walk from 7:30 a.m. to noon, and its Main House Trick-or-Treat tours run from 1 to 4 p.m. The Town's Oyster Bay Harbor Cleanup starts at 9 a.m. at Theodore Roosevelt Park, Centre Island Beach and Stehli Beach, the same week the festival leaves the park. At Sagamore Hill, 20 Sagamore Hill Road, the National Park Service calendar lists an Autumn Nature Walk at 12:30 p.m. and a talk on the Theodore Roosevelt Presidential Library at 3 p.m.
The Season on Either Side
The festival weekend sits in the middle of a calendar that starts a week earlier and continues until just before Thanksgiving.
| Date | Event | Where |
|---|---|---|
| Oct. 10, 4:30–8:30 p.m. | Pirates and Patriots: a sail aboard the oyster sloop Christieen, then an evening at Raynham Hall; $80 adults, $60 under 21, capped at 21 guests | The WaterFront Center, 1 West End Ave. |
| Oct. 17–18 | 43rd Oyster Fest | Theodore Roosevelt Memorial Park and Audrey Avenue |
| Oct. 17 | Oudolf Garden opens | Planting Fields, 1395 Planting Fields Road |
| Oct. 23–25, 30–31, 1–4 p.m. | Main House Trick-or-Treat tours; $15 adults, $14 seniors, $5 children, free for ages five and under | Planting Fields |
| Oct. 24, 9 a.m. | Oyster Bay Harbor Cleanup | Theodore Roosevelt Park, Centre Island Beach, Stehli Beach |
| Oct. 30, 6–8:30 p.m. | Halloween Ghost Walk & Dance Party | From Oyster Bay High School, 150 E. Main St., to the bandstand in Townsend Park |
| Oct. 30, 7:30–9 p.m. | Tarot & Tales: A Night with the Spirits; $75 | Raynham Hall Museum |
| Nov. 6, 10–11 a.m. | First Fridays: The Wonderful World of Everett Shinn, with a look at the restored Tea House | Planting Fields |
| Weekends through mid-November, noon–4 p.m. | Theodore Roosevelt: The Man in the Arena | Oyster Bay Railroad Museum station, 1 Railroad Ave. |
| Nov. 21–22, 11 a.m.–4 p.m. | Railroad museum model train show fundraiser | Hicksville Community Center |
The longest-running item is at Raynham Hall Museum, 20 West Main St. Its new exhibition, "Revolutionary Oyster Bay: 275 Years," opened with the museum's first catalog and stays on view through March 28, 2027. That's a good indoor plan for a raw November weekend, around the time the Oudolf Garden's bulbs are going into the ground.
At Farber Locke Team, we keep a close eye on the Oyster Bay calendar because the things that shape a year here, from the festival weekend to a new garden up the road, also shape how a home here is valued. If you're curious what your Oyster Bay home is worth this fall, start with our instant home valuation, and we'll follow up with the local context behind the number.
