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Downtown Freehold has a full holiday calendar lined up for 2026, from a tree lighting at the Hall of Records on Tuesday, December 1 to Jolly Trolley rides, brunch with Santa and a community sing along before Christmas. Here is what is happening in the county seat this season and when.
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Tree Lighting and Holiday Vendor Village
- Town: Freehold Borough
- Where: Monmouth County Hall of Records, Main Street, Freehold
- When: Tuesday, December 1, 2026, 5 p.m. to 7 p.m. (rain date Wednesday, December 2)
The season officially starts downtown when the holiday tree lights up outside the historic Hall of Records. The Rock and Roll Choir is scheduled to perform, Court Jester will serve hot cider, and the evening includes a holiday vendor village for early shoppers. The Freehold Fire Department may also stop by with a special guest, so bring the kids and a camera.
Brunch with Santa at The American Hotel
- Town: Freehold Borough
- Where: The American Hotel, downtown Freehold
- When: Sundays, November 29, December 6, December 13 and December 20, 2026, 10 a.m. to 3 p.m.
Santa joins brunch on four Sundays this season at The American Hotel. Reservations are required, so call 732-431-3220 to save a table, especially for the Sundays closest to Christmas.
Menorah Lighting
- Town: Freehold Borough
- When: Tuesday, December 8, 2026, 4 p.m. to 5 p.m.
Downtown Freehold celebrates Hanukkah with a menorah lighting during the festival of lights, a short and meaningful early evening gathering for the whole community.
Jolly Trolley
- Town: Freehold Borough
- When: Friday, December 11, 2026, at 5, 6, 7 and 8 p.m.; Saturday, December 12 and Sunday, December 13, hourly from 3 p.m. through 8 p.m.
The Jolly Trolley, sponsored by Shore Luxury Limos, runs holiday rides on the hour across one December weekend downtown. Tickets are sold through the Downtown Freehold website store and are nonrefundable unless the event is canceled, so pick your time slot carefully.
Breakfast with Santa at Sweet Lew’s Cafe
- Town: Freehold Borough
- Where: Sweet Lew’s Cafe, downtown Freehold
- When: Saturday, December 12, 2026, 9 a.m. to 12:30 p.m.
For families who prefer a Saturday morning visit with Santa, Sweet Lew’s hosts breakfast with the big guy. Reservations are required at 732-308-1887.
Caroling and Holiday Sing Along
- Town: Freehold Borough
- Where: The Holiday Tree at the Monmouth County Hall of Records
- When: Thursday, December 17, 2026, 6 p.m. to 8 p.m.
Peter Guarino and a group of carolers lead a holiday sing along around the downtown tree a week before Christmas. It is a cozy way to wrap up an evening of shopping on Main Street.
Downtown Freehold is also planning more holiday fun, including a Gingerbread House Contest, with details posted on the Downtown Freehold website as they are announced. Make a day of it with lunch, shopping at local boutiques and a stroll under the lights. For more holiday events across the county, keep following Shop Monmouth County.
Photo: Freeholdman12, CC BY-SA 4.0, via Wikimedia Commons
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