The Parking Pass Is What Pays for Christmas in Middleburg

In 1979, Mayor Loyal McMillin said Middleburg needed a Christmas celebration. A year later, Dudley and Cissy Bunn and Tyler Gore organized the first modern parade, according to the Middleburg Eccentric's history of the event. For years the Middleburg Business and Professional Association ran it. Jim Herbert led it through the 2010s and turned it into a nonprofit in 2011.

Forty-six years later, the day costs about $150,000 to put on. Most of that money comes from cars parked in a field at Mickie Gordon Park and on the grounds of Lost Barrel Brewing. The Middleburg Hunt's horses and hounds step off down Washington Street at 11 a.m. on Saturday, December 5. The community parade follows at 2 p.m., with carolers and a kids' zone at the Middleburg Community Center in between. The parade is a little more than three weeks away, and this year the parking pass is carrying more of the weight than usual.

Where the Money Came From in 2025

Christmas in Middleburg is a 501(c)(3) that files a budget and a statement of activity with Town Council every year. That makes its finances unusually easy to read. For 2025, the nonprofit reported $151,529 in income and about the same in expenses.

"80% of our incoming revenue is parking and VIP offers in town. Only 20% is raised by sponsorships," co-organizer Michelle Myers told the Eccentric. Her split covers what visitors and sponsors pay. In the 2025 filing, parking and VIP receipts together came to $86,425, compared with $27,300 from sponsors. The gifts went to the Hill School, Foxcroft, Middleburg FISH and the Middleburg Hunt, among others. That came to nearly 10 percent of the year's spending.

The event used to be much smaller. When the Eccentric reported the 2016 parade's finances, income was $78,000, including $9,000 from the Town. In less than a decade the budget has nearly doubled, and much of that growth traces back to one decision about where visitors park.

Why the Biggest Bill Is a Bus

The largest single cost of the day is the shuttle contract, about $39,000. All bus spending last year came to $40,857, according to the filing. Michelle Myers told the Eccentric the buses became essential when the Town closed in-town street parking to parade visitors after the event returned from its 2020 COVID cancellation. The Town has also asked organizers to cap parking at 1,000 cars.

So the system that keeps cars off Washington Street is the same one that pays for the parade. A pass pays for a seat on a bus that only runs because visitors can no longer park in the village, and the same money goes on to cover the barricades, insurance and charitable gifts. The nonprofit pays Loudoun County Sheriff's deputies to direct traffic off Route 50 and buses out of Mickie Gordon Park. It also donates to the Aldie Ruritans, who help run the parking there.

The Town's part is set out in a memorandum of understanding that Council approved unanimously in July 2025. The nonprofit carries the financial and contractual obligations. The Town provides police and staff, and the Middleburg Police chief sets the parade route and has the final word on whether it goes on. For 2026, the Town budgeted a $12,000 sponsorship, up from $10,000. It is also covering police overtime, officers from other jurisdictions and public works help, according to Interim Town Manager Will Moore.

What That Means for December 5

Because the parking caps how many cars come in, passes run out early. The 2026 standard parking and shuttle pass at Mickie Gordon Park was listed at $50 per car on TicketLeap and is marked sold out. Online sales for VIP parking and shuttle service at Lost Barrel Brewing, one mile west of town on Route 50, are closed. The listing asks buyers to contact the organizer about availability. Neither lot sells passes on the day.

For anyone holding a pass, or bringing guests who have one, the day runs on the bus schedule:

1. Friday, December 4. The Town of Middleburg Tree Lighting takes place at the Middleburg Museum's Pink Box, 8 North Madison Street, according to the Red Fox Inn's events page.
2. Saturday morning. The Middleburg Community Charter School PTO lists Breakfast with Santa for December 5 on its site. Shuttles from both lots start at 8:30 a.m.
3. 10:15 a.m. The last shuttle that gets riders in for the Hunt Review leaves the Mickie Gordon lot, because Route 50 closes. Drivers to that lot enter from Oakham Road only.
4. 11 a.m. The Middleburg Hunt's horses and hounds come down Washington Street.
5. Midday. Carolers and the kids' zone run at the Middleburg Community Center.
6. 1:15 p.m. The last shuttle that gets riders in for the parade departs.
7. 2 p.m. The community Christmas parade begins.
8. 6 p.m. Shuttle service from the lots ends.

A few details that matter on the day. Well-behaved pets can ride, but only on the clearly marked pet buses. Free handicap-accessible parking is behind Middleburg United Methodist Church at 15 West Washington Street, for vehicles with a valid DMV sticker or hang tag. That lot comes at a cost too. Organizers rented it with a $3,000 donation, and in September Council adopted the parking ordinance that allows the church to rent it, as the Eccentric's September council report noted.

Seats along the route are another source of income. The 2026 Grandstand Seating or Sip & See Dining package is based at the corner of North Madison and West Washington Streets from 10 a.m. to 5 p.m. and is for ages 21 and over. You choose either a reserved bleacher seat with a lap blanket or a private table served by The Oyster Bar, with a bottle of champagne and four branded carafes. These are the "VIP offers" in Michelle Myers's 80 percent.

A Presenting Sponsor Still Unconfirmed in Late October

Sponsorship is where 2026 differs. PenFed, the federal credit union, was presenting sponsor in 2024 and 2025. At the September 24 Council meeting, Doug Myers said the event had no presenting sponsor, leaving "an approximate $20,000 shortfall," and that "this event is in real risk of ending" without significant financial support, as the Eccentric reported. On October 28, Michelle Myers told the Eccentric in writing that she was "in active talks with a potential sponsor that will fill the gap, but no confirmation yet." She added that organizers would return to Council in November if needed.

Sponsorship had already been falling short. The 2025 budget counted on $57,000 from sponsors, $35,000 of it from a presenting sponsor. Actual sponsorships came to $27,300, and individual donations and VIP sales covered most of the difference. Michelle Myers has told Council that costs rise "5 to 7% every year."

The reserve is smaller than its headline number. The nonprofit had $79,180 in the bank as of February 23, 2026, and no debts. About $66,000 of that is the operating account. Organizers spend $40,000 to $60,000 of it on vendor deposits starting in July, before any parking is sold in September. The Eccentric calculated that this leaves a cushion of somewhere between $6,000 and $26,000 to absorb a missing $20,000 sponsor. Organizers say they will move out of their office space at the end of 2026 and cut back on social outreach and admin support.

What Neighbors Can Do Before the Horses Step Off

The suggestions so far are small and specific. At the September meeting, Mayor Bridge Littleton suggested the Middleburg Business and Professional Association ask each member to "chip in 200 bucks." Council member Pam Curran directed organizers to the Middleburg Charitable Foundation, which takes grant applications in October.

For individuals and local businesses, the sponsorship page lists tiers from a $25,000 presenting partnership down to a $12,000 Christmas Spirit sponsorship, a $2,500 Angel level, a $1,000 Band level and a $500 Kid's Zone level. Organizers recently added family sponsorships and can be reached at [email protected]. "We can take sponsorship help all year round," Michelle Myers said. The nonprofit also sells its annual Christmas ornament through its online shop. A separate donation account of about $11,900 pays for producing the ornament and for the year's charitable gifts.

Doug and Michelle Myers started volunteering with the event in 2018 and became its part-time co-organizers in 2022. Both put their own businesses on hold for the four weeks before the parade to answer thousands of emails, calls and texts. Those four weeks have begun. Parking and VIP sales remain the event's main income. With no presenting sponsor confirmed as of October 28, a family sponsorship or an ornament now helps the parade more than it would in a typical year.

At Kristin Dillon-Johnson, we count the first Saturday in December among the days that tie Hunt Country together, from the hounds on Washington Street to the volunteers directing cars on Oakham Road. If you're hosting family that weekend and want suggestions for where to stay in the countryside or how to work the shuttle schedule into your plans, schedule a free consultation and we'll talk it through over coffee before the parade.