Bedford's November Has One Ticketed Weekend and a Month of Drop-Ins
October 29, 2026
October 29, 2026
In Bedford this November, how you get in matters more than the date. The Fine Day Holiday Fair returns to Bedford Post Inn on November 7 and 8. Each ticket comes with an arrival window and assigned parking for the car it arrives in, and no tickets are sold at the door. Nearly everything else on the November calendar runs the other way. A jazz quartet at the Playhouse is free and needs no reservation. Mahjong is on the schedule three days a week between the library and the Playhouse. Later in the month, the town's Holiday Market sets up at the Bedford Hills train station.
So in practice, Bedford's November has one weekend you have to plan around. The rest of the month you can just show up for.
The Fine Day Holiday Fair runs 9 a.m. to 4 p.m. both days at 954 Old Post Road, with 50 vendors. The ticket tier you buy sets two things: when you can arrive and where you park.
| Ticket | Arrival window | Price | Where the car goes |
|---|---|---|---|
| First Arrivals | 9 to 11 a.m. | $60 plus tax | On site at Bedford Post Inn while space lasts, then Cloverly Farm |
| Late Morning | 11 a.m. to 1 p.m. | $50 plus tax | Cloverly Farm, 921 Old Post Road, across the street |
| Afternoon | 1 to 4 p.m. | $40 plus tax | Bedford Village Elementary School, 45 Court Road, with a complimentary shuttle |
The arrival window only controls when you come in. The organizer's FAQ says there is no required departure time, so a 9 a.m. arrival can stay until close. The Late Morning lot at Cloverly Farm comes with an assisted pedestrian crossing to the Inn.
The organizer's own ticket copy shows how fast these sell:
"Last year's Holiday Fair sold out in less than two weeks."
This year looks similar. In late October, every Saturday tier showed sold out. On Sunday, First Arrivals and Late Morning were gone, and only the Afternoon session with the school-lot shuttle could still be booked. Availability changes quickly, so check the ticket page before you plan around it.
A few details in the FAQ matter if you're going with family or neighbors. Every person needs a ticket, but parking goes by the driver's ticket. A driver with a First Arrivals ticket can park at the Inn even if the passengers hold tickets for later windows. The FAQ is also more careful than the checkout page. The ticket listing calls First Arrivals parking guaranteed. The FAQ says on-site parking is "subject to availability" and that First Arrivals drivers go to Cloverly Farm once the Inn's lot is full. The organizer asks people to carpool. It also asks anyone who lives close enough to be dropped off and picked up instead. For anyone in Bedford Village, that's the simplest way to go.
Bedford Post Tavern runs the food on fair weekend. It sells food and drinks at an outdoor kitchen and takes sit-down reservations for breakfast, lunch and dinner on both November 7 and 8. The organizer warns that lines may form at peak times. It suggests bringing snacks and water for children or anyone with dietary needs.
The Tavern's regular weekend schedule sets the times. Breakfast runs 7:30 to 10:30 a.m., brunch 10:30 a.m. to 3 p.m., and a midday menu 3 to 5 p.m. Dinner is 5 to 10 p.m. on Saturday and 5 to 9 p.m. on Sunday. Table bookings go through Bedford Post Tavern on Resy. Dinner starts an hour after the fair closes at 4 p.m. If you want a table at the Inn that Saturday or Sunday, plan on booking it like a fair ticket and not as a walk-in.
Back toward the village, Bedford Playhouse at 633 Old Post Road has a busy week around the fair. Its café and Bambi's Bar are open Tuesday through Sunday, 11:30 a.m. to 8 p.m. Doors sometimes open earlier on days with early screenings. Outside food and drink aren't allowed.
Fair week at the Playhouse, day by day:
Friday's jazz is the opposite of the fair. On the night before the busiest weekend on Old Post Road, a live set at the Playhouse is free and needs no reservation.
The rest of the month includes:
Mahjong is the most regular thing on Bedford's November calendar. Between the Playhouse and the Bedford Free Library, a game is scheduled every Wednesday, Thursday and Friday for most of the month, with one Tuesday night added on November 17.
The Playhouse's Mahjong Lunch & Lesson meets Wednesdays at 1 p.m. on November 4, 11, 18 and 25 and runs about two hours. Mahjong Nights at the Playhouse adds an evening on Tuesday, November 17, at 6:30 p.m., with a lesson or open play. The library covers Thursdays and Fridays with Drop-In Mahjong from 10 a.m. to noon, including November 5, 6, 12 and 13.
The library schedule has other regular drop-ins too. Sip & Stitch meets Wednesday evenings from 6 to 7:30 p.m. Afternoons with Alix offers tech help from 2 to 6 p.m., and Stories, Songs and Surprises is at 11:15 a.m. on Thursdays.
Fair Saturday also has a free option for families. At the Bedford Hills Free Library, Puzzles and Playdough runs from 10:30 to 11:30 a.m. on November 7. Kitten Corner with Rock n' Rescue follows from 11 a.m. to noon. The same library is closed on November 11 for Veterans Day. On November 12 it hosts Community Perspectives on Sustainable Living, an offsite program from 7 to 8:30 p.m.
The month's other holiday shopping day doesn't take place on Old Post Road. The Town of Bedford's Holiday Market runs Saturday, November 21, from 11 a.m. to 3 p.m. at the Bedford Hills Train Station. It's listed on the town's Recreation & Parks calendar. The listing doesn't mention timed entry or tiered parking.
The same Saturday is also the last day of the John Jay Homestead Farm Market's extended 2026 season, from 9 a.m. to 2 p.m. at Lot 2, 190 Katonah Avenue. If you're going to both, you'll be driving between Bedford Hills and Katonah. The two schedules overlap from 11 a.m. to 2 p.m.
Old Post Road gets one more turn before the year ends. The Bedford Historical Society lists Fezziwigs on Friday, December 4, from 5 to 6 p.m. at 612 Old Post Road. That's just down the road from the Playhouse at 633.
The Fine Day weekend is the one that needs planning. If you hold a Sunday afternoon ticket, the shuttle leaves from the Court Road school lot, and the doors close at 4 p.m.
At Durr Palumbo Partners, we pay attention to weekends like this one because they shape what a home on Old Post Road is like to live in. If you're curious how that stretch of Bedford affects the value of your home, we'd be glad to talk it through. Request a Home Valuation.
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