"Keep your eyes on the stars and keep your feet on the ground." Those words are on a plaque set in a rock beside Theodore Roosevelt's grave in Youngs Memorial Cemetery on Cove Road. The Town of Oyster Bay lists the cemetery's address as Oyster Bay Cove.
The Halloween events on Friday, October 30 and Saturday, October 31 are spread across Oyster Bay Cove and nearby Oyster Bay hamlet. Much of that ground is tied to Roosevelt. A guided hike starts near the corner where his statue stands. His grave and the songbird sanctuary next to it sit on the village's own road. Free grounds tours run at his home next door. On Friday night, the town's Halloween parade will end at the bandstand named for his daughter, which replicates one he once spoke from. Here is how October 30 and 31 line up.
Friday at 10 a.m., a guided hike near Berry Hill Road
The weekend's first scheduled event is in the woods. The September–October 2026 newsletter from the Oyster Bay–East Norwich Public Library lists a moderate 2.5- to 3-mile hike through Tiffany Creek Preserve with Lee McAllister at 10 a.m. on Friday, October 30. Registration opened September 18, so call the library before you show up to see if spots are left.
The hike covers more ground than most people expect. The Town of Oyster Bay's preserve guide calls Tiffany Creek a 197-acre preserve pieced together from parts of three former estates. Its trail drops through glacial ravines from an oak hilltop and upland meadow. Tuliptree, red oak and red maple fill the lower slopes, and there's a wet meadow at the northeast edge. The entrance is on Sandy Hill Road near Berry Hill Road.
The same guide places a 12-foot statue of Roosevelt on horseback at the corner of Route 106 and Berry Hill Road. The Rotary Club of Oyster Bay commissioned it in 2005 from the original casting of Alexander Phimister Proctor's 1921 "Theodore Roosevelt-Rough Rider."
If you'd like a shorter walk, the Cordelia Hepburn Cushman Preserve on Route 25A in Oyster Bay Cove has 15 wooded acres, open sunrise to sunset. Parking is limited.
On Cove Road, the sanctuary and the grave share a property line
Cove Road is the stretch of the Roosevelt story that sits fully inside the village. The Theodore Roosevelt Sanctuary and Audubon Center at 134 Cove Road opened in 1923 as the country's first National Audubon Society songbird sanctuary. Audubon says Roosevelt's gravesite sits at the edge of the sanctuary property. Its 14 acres hold native plant demonstration gardens, several small ponds, a mile of hiking trails and a Bessie Potter Vonnoh fountain sculpture.
The trails and gardens are open sunrise to sunset. Audubon asks for a $5 trail-use donation. Its listing for the visitor building has been inconsistent, so plan on the trails alone.
Youngs Memorial Cemetery has been a burial ground since the 1600s. It's where Theodore and Edith Kermit Roosevelt are buried, under a plain granite headstone with both names and the Presidential Seal. You reach the hillside grave by climbing 26 steps, one for each step to the 26th presidency. From now through the end of the year, the cemetery is open 9 a.m. to dusk, weather permitting. Late October brings early sunsets, so on a Saturday you can fit in the grave and the sanctuary loop before lunch and still reach the hamlet by noon.
A burial ground since the 1600's, Youngs Memorial Cemetery is the final resting place of President Theodore Roosevelt and his wife, Edith Kermit Roosevelt.
From the Town of Oyster Bay's guide
Next door, Sagamore Hill runs free grounds tours both mornings
The National Park Service calendar lists a Guided Grounds Tour at Sagamore Hill at 10:30 a.m. on both Friday, October 30 and Saturday, October 31. That makes it the one Roosevelt site with a guide on both days of the weekend. The grounds tours are free and are listed on Recreation.gov for Fridays through Sundays.
Getting inside the house takes more planning. According to the NPS tour page, home tours need advance online reservations and run Thursday through Sunday. The house is closed Monday through Wednesday, and a tour lasts about 45 minutes. Prices are $15 for adults, $7.50 for seniors 62 and older and for qualifying military members and veterans, and $1 per child reservation. Recreation.gov releases 2 and 3 p.m. tickets at 9:30 a.m. the day before. Noon and 1 p.m. tickets may go on sale at 9:30 a.m. the same day, depending on staffing.
The grounds are open year-round, free, from sunrise to 30 minutes after sunset. The Old Orchard Museum is open Thursday 1 to 4:30 p.m. and Friday through Sunday noon to 4:30 p.m. Don't plan on picking up a book on the way out. The NPS current conditions page has listed the Eastern National Bookstore and Gift Shop as closed until further notice since an alert posted October 2, 2026. The same page notes phone problems and asks visitors to use email. The Park Service last updated its hours page in 2025, so check it once more before you head out.
Friday night, the parade finishes at a bandstand built for Roosevelt history
The Roosevelt route ends downtown. Raynham Hall Museum's Oyster Bay Halloween Ghost Walk & Dance Party runs from 6 to 8:30 p.m. on Friday, October 30. It starts at Oyster Bay High School, 150 East Main Street, heads west to Audrey Avenue Extension, and ends at the Derby-Hall bandstand in Townsend Park. The museum points out one change this year: the parade ends at the bandstand itself, not the parking lot.
The museum asks everyone to come in costume and bring lanterns and noisemakers. Pets are welcome too; the listing invites ghosts and goblins of the "two & four-legged varieties." The party has a DJ, John Hubbard, who volunteers. Food and drink vendors are Gimme Burger, Oyster Bay Brewing, Outlaw Street Eats, Penelope Bean & Co. Coffee and The Toy Box. Raynham Hall is also looking for volunteers to carry the parade's large ghost puppets.
The Town's guide describes the Derby-Hall Bandstand, built in 1980, as an exact replica of a 1909 bandstand. Roosevelt used the original for a July 4th speech in 1916. The replica is named for Ethel Carow Roosevelt Derby, one of his daughters, and for former Congressman Leonard W. Hall, her godson, who came up with the idea of rebuilding it. A cannon sits at each corner of Townsend Park. One is a Civil War Dahlgren rifle carrying a bronze tablet cast from metal recovered from the USS Maine.
Adults have a second option that night. Raynham Hall's Tarot & Tales: A Night with the Spirits runs from 7:30 to 9 p.m. at the museum, 20 West Main Street. Tickets are $75 and include a five-minute personal tarot reading.
Saturday, the trick-or-treat trail and the newer tables share the same blocks
On Halloween itself, the Oyster Bay Main Street Association runs Boo-tiques by the Bay from noon to 2 p.m., with costumes, treats and stops at participating shops. Newsday's 2026 Halloween guide puts the trail along Audrey Avenue, East and West Main streets, South Street and the gazebo across from Town Hall.
Several of the businesses on those blocks are new since you last trick-or-treated here:
- HOSHI, 34 Audrey Avenue. This Japanese restaurant opened October 5, 2026, which makes this its first Halloween. Long Island Wave reported that it opens daily at noon and closes at 10 p.m. Sunday through Thursday and 11 p.m. Friday and Saturday. The restaurant says hours may change. Its website lists a Chef's Omakase Tuesday through Saturday at 7 p.m. for parties of two to four, booked at least 24 hours ahead.
- The Bay Butcher, 96 South Street. Patch reported that this family-owned butcher shop opened in early May 2026.
- Bull Moose, 108 South Street. This members-only cocktail lounge and cultural salon sits behind Provisions Market. Long Island Business News reported its opening in March 2026 and said the name nods to Roosevelt's run with the Progressive Party, better known as the Bull Moose Party.
These are the same blocks that hosted the 43rd Oyster Fest on October 17 and 18. Newsday listed the festival on Audrey Avenue and in Theodore Roosevelt Memorial Park, two weeks before Halloween.
After Halloween, the November dates to keep
Once the weekend is over, the calendar gets lighter. These are the dated events through Thanksgiving:
- Saturday, November 7, 1 p.m. The Town Historian gives a free talk, "Oyster Bay: As It Was A Century Ago," at the Oyster Bay Community Center on Church Street. The date was rescheduled, and registration is required, according to the Town of Oyster Bay.
- Weekends through mid-November. The Oyster Bay Railroad Museum at 102 Audrey Avenue keeps regular weekend hours of noon to 4 p.m., with turntable rides on Saturdays in season, weather permitting.
- November 21 and 22, 11 a.m. to 4 p.m. The museum's Annual Model Train Show Fundraiser moves to the Hicksville Community Center.
- Thursday, November 26. Sagamore Hill closes for Thanksgiving.
The Cove Road trails keep their sunrise-to-sunset hours through all of it, and the cemetery stays open until dusk.
Batul has spent more than 30 years on the North Shore and knows how much of Oyster Bay Cove's daily life happens on its wooded roads and just down the hill in the hamlet. If you're wondering how your home on one of those roads would come across to buyers who care about the same places, Batul Morbi and her team would be glad to walk you through it. Start with a private home valuation, or read more about the Oyster Bay Cove market.
