Montgomery's Holiday Weekend Starts on Clinton Street and Ends at the Tracks

On Saturday, December 13, 2025, at about 5:15 p.m., the tree at Village Hall lit up in bright blue. A tractor parade decked out in lights closed out the day. The next afternoon, around 1:45, Santa was standing beside the tracks on Railroad Avenue while volunteers loaded new, unwrapped toys for children across Orange County. That year the Marines who usually distribute those toys had been deployed. According to the Wallkill Valley Times, the drive went on anyway because Village Event Coordinator Tracey Kazie, County Executive Steve Neuhaus and Marine veteran Vinny Serrano stepped in, and Kazie and other volunteers sorted and handed out the county's toys in the Marines' place.

That weekend is basically the village's whole holiday season. It lasts about 30 hours, from Saturday on Clinton Street to Sunday on Railroad Avenue, and it is run by the fire department, churches, a Scout troop, village volunteers and a short-line railroad. The November events lead up to it. This year it falls on December 12 and 13.

Two Days, Two Streets

The Village of Montgomery's Old-Fashioned Christmas is set for Saturday, December 12. Judi Van Nosdall's October 22 column in the Wallkill Valley Times says more details will come as plans are finalized. The same column says the Toys for Tots Toy Collection Train will stop in the village on Sunday, December 13. The train schedule is already published.

Saturday is the day still waiting on details. Last year's event is the best guide to what it will probably look like.

What Saturday Looked Like Last Year

The 2025 edition, called An Olde Fashioned Holiday, ran from 9 a.m. to 6 p.m. Nearly every piece of it came from a local group:

• Craft vendors along Clinton Street
• Tree and wreath sales by the Montgomery Fire Department and Boy Scout Troop 31
• A live Nativity at First Presbyterian Church
• Wagon rides from Norbury "Skip" Chambers
• Hot cocoa from St. Mary's Knights of Columbus
• Santa arriving on a fire truck and posing for photos at the Clinton Street Bandstand
• The Village Hall tree lighting around 5:15 p.m., then the lighted tractor parade

The 2024 coverage shows the same basic plan with a few differences. First Presbyterian sold soup to go as a fundraiser and Valley Central students sang. The tractor parade, organized by Village Trustees Kevin Conero and Randy Wilbur, started around 4:30 p.m. on Wallkill Avenue, and the crowd moved to Village Hall for the tree lighting afterward. That year the parade came before the lighting. In 2025 the lighting came first. Both years ran from late morning shopping on Clinton Street to a lit tree at dusk. The 2026 order is up to the organizers, and the village hasn't announced it yet.

Sunday Belongs to the Railroad

The Sunday stop belongs to a bigger operation. On December 13, the Middletown & New Jersey Railroad runs Orange County's leg of Operation Toy Train. The stops, in order:

1. Warwick, Visitor Information Caboose, 25 South St., 9:45 to 10:20 a.m.
2. Sugar Loaf Station, 1398 Kings Hwy., 10:35 to 11:10 a.m.
3. Montgomery "Lumber Lot," 46 Railroad Ave., 12:45 to 1:55 p.m.
4. Campbell Hall, Hamptonburgh Caboose Museum, 3 Erie St., 2:20 to 3:30 p.m.
5. Middletown–Walkill Train Station, 301 N. Galleria Dr., 4:05 to 4:30 p.m.
6. Port Jervis Railroad Museum, 86 Pike St., 5:35 to 6:15 p.m.

Montgomery has 70 minutes on the schedule. That ties Campbell Hall for the longest stop of the day and is about double the 35 minutes at Warwick or Sugar Loaf. The schedule says toys collected on the Orange County run go to the Marine Toys for Tots Foundation's county toy drive and are given to children in Orange County. Toys dropped off at Port Jervis go to local Easter Seals and Salvation Army drives instead. Bring new toys and leave them unwrapped. The organizers ask donors not to use wrapping paper.

The printed times are a plan, and the train has run on a different clock before. In 2024, the train pulled in at 12:45, and volunteers spent about an hour loading toys while Santa worked through a long line. In 2025, the Times reported Santa arriving around 1:45 for about half an hour. To be safe, get there for the 12:45 arrival.

The October column also asks for help with one group in particular. Gifts for older children are especially needed, so remember the teenagers.

November Builds Toward It

The November events are mostly about shopping, and that shopping heads toward the toy train.

Saturday, Nov. 7. The annual Orange County Farm Toy Show runs 9 a.m. to 3 p.m. at the Maybrook Senior Center, 2 Senior Way. Proceeds benefit the Orange County Farmers Museum. The show has new and used farm toys, memorabilia, a farm display contest, kiddie tractor pulls starting at noon, silent auctions and an outdoor tractor display. A new farm toy bought here could go straight onto the train five weeks later.

Friday, Nov. 13. Ladies Night Out runs 4 to 9 p.m. at 17 local businesses, and more may join. Rachel Santana is the contact, at 845-728-4470 or [email protected].

Saturday, Nov. 21. The Valley Central Scholarship Council Holiday Craft Fair runs 10 a.m. to 3 p.m. at Valley Central High School, with vendors, raffles and food.

The calendar also includes a few events for veterans and older residents. The Village of Montgomery Senior Center hosts a Veterans Luncheon on Tuesday, Nov. 10, from 11 a.m. to 2 p.m. Space is limited, and the center asks people to call Jo-Ann at 845-457-9367 soon. The village's Community Blood Drive comes three days after the train, on Wednesday, Dec. 16, from noon to 5 p.m. You can book through RedCrossBlood.org with the code VOM.

A Village With Fewer Tables

This year the holiday weekend comes to a village that recently lost two places to eat. Hudson Valley Post reported that Antonio's Family Restaurant's last day was Sunday, Sept. 20, and that Vic's Pizza closed for good four days later, on Thursday, Sept. 24, 2026.

In posts quoted by Hudson Valley Post, Mayor Mike Hembury called Antonio's "a true cornerstone of our village, a gathering space for neighbors." He said Vic's was a place "where friends could meet, families could gather, and everyone felt at home." Another village pizzeria, Cascarino's, wished both owners well and asked residents to be patient with the remaining restaurants as they handle more business.

That matters on a Saturday that ran from 9 a.m. to 6 p.m. last year. There are now fewer dining rooms in the village to feed that crowd. In her column, Van Nosdall recommends her favorite, Francesca's on Ward Street, and notes that the old Corner Deli is being renovated. No new business there has been announced. Saturday's food also comes from the event itself. In recent years that has meant soup to go from First Presbyterian and cocoa from the Knights of Columbus.

The Old-Fashioned Christmas is Saturday, Dec. 12, on Clinton Street. The toy train is Sunday, Dec. 13, at 46 Railroad Ave., arriving at 12:45 p.m.

A home on or near Clinton Street comes with a front-row seat to this weekend, and that is part of what the next owner is buying. If you're thinking about selling a home in or around the village in the new year and want a plan for preparing and timing it, Kathryn DeCrosta is available to talk it through. Call or Text to Connect.