Christmas in Middleburg Runs on Parking Passes. This Year, That Matters More.

"Without significant financial support, this event is in real risk of ending." Doug Myers told Middleburg Town Council that on September 24, according to the Middleburg Eccentric. He co-organizes Christmas in Middleburg with his wife, Michelle. The event had no presenting sponsor, which left a shortfall of about $20,000.

The parade is still on. It's set for Saturday, December 5. The Middleburg Hunt's horses and hounds step off at 11 a.m., and the community Christmas parade follows at 2 p.m. Between the two there are carolers and a kids' zone at the Middleburg Community Center. What's less settled is the money behind it, and that money depends heavily on one thing locals tend to complain about: parking. On October 28, Michelle Myers told the Eccentric she was "in active talks with a potential sponsor that will fill the gap, but no confirmation yet."

Where the Money Came From in 2025

Christmas in Middleburg is a 501(c)(3) nonprofit. Each year it files its budget and a statement of activity with Town Council, so its finances are public. For 2025, it reported $151,529 in income and about the same in expenses. Here's where that income came from, by the Eccentric's breakdown:

Parking and VIP sales together brought in $86,425 in 2025, more than half of all income and more than three times what sponsors gave. Michelle Myers put it more broadly to the Eccentric: "80% of our incoming revenue is parking and VIP offers in town. Only 20% is raised by sponsorships." Sponsorship came in light last year as well. The 2025 budget counted on $57,000 from sponsors, $35,000 of it from a presenting sponsor, and sponsors actually gave $27,300. Individual donations and VIP sales made up most of the gap. PenFed, the federal credit union, was the presenting sponsor in 2024 and 2025. As of late October, no company had taken its place for 2026.

The event has also grown a lot. When the Eccentric reported on the 2016 parade's finances, income was $78,000, including $9,000 from the Town. Michelle Myers told Council that costs rise "5 to 7% every year."

Why Parking Became the Business Model

The single biggest cost is the bus fleet that brings visitors in from lots outside the village. That was $40,857 in all for 2025, according to the filing. Barricades and portable toilets ran about $15,000, and insurance about $6,000.

The buses became essential after the parade came back from its 2020 COVID cancellation. That's when the Town closed in-town street parking to parade visitors, Michelle Myers told the Eccentric. The Town has also asked organizers to cap parking at 1,000 cars. So the shuttle system that moves visitors past residents' front doors without filling the side streets also brings in most of the parade's revenue. Every pass bought for Mickie Gordon Park helps pay for the bus that keeps that car off Washington Street.

Parking money also flows back into town. In 2025 the nonprofit gave $13,923, nearly 10 percent of its spending, to local schools, churches and charities, including the Hill School, Foxcroft, Middleburg FISH and the Middleburg Hunt. It pays Loudoun County Sheriff's deputies to direct traffic off Route 50 and buses out of Mickie Gordon Park, and it donates to the Aldie Ruritans, who help run the parking there.

A parade funded by parking passes depends on big crowds. Town Manager Danny Davis estimated the 2025 parade drew about 10,000 people, according to the Eccentric's December 2025 Town Council report. In that report, Punkin Lee, president of the business association, asked that merchant parking and drivers getting around the barricades be addressed this year.

Parade Day, Step by Step

The organizer's parking page and the 2026 schedule of events cover what anyone driving in needs to know. The schedule says no parking is available in town or along Route 50 that day, and towing is enforced.

1. Pick a lot. Priority parking is at Mickie Gordon Park, one mile east of town on the north side of Route 50. Turn north onto Oakham Road, then take Carters Farm Lane to the park entrance. VIP parking is one mile west of town at Lost Barrel Brewing, also on the north side of Route 50. Shuttles serve both lots from 8:30 a.m. to 6 p.m.
2. Buy early. Northern Virginia Magazine reported that passes opened October 1 at $50 for Mickie Gordon Park and $110 for Lost Barrel, with prices set to rise as the date approached. As of October 31, the organizer listed $60 and $150 per car, shuttle included.
3. Use the accessible lot if you qualify. Free parking behind Middleburg United Methodist Church at 15 West Washington Street is open to vehicles with a valid DMV sticker or hang tag.
4. Reserve a spot to watch from if you want one. The organizer sells reserved viewing spots on Washington Street and front-row seats at the grandstand or The Oyster Bar.
5. Start with breakfast. Middleburg Community Charter School at 101 N. Madison Street hosts Breakfast with Santa that morning, with food by Tutti Perricone of Back Street Catering. The school's PTO promotes it as "THE BEST (and cheapest) PARKING IN TOWN," and tickets are sold through the MCCS PTO. Northern Virginia Magazine lists it from 8 to 11 a.m.

Under the memorandum of understanding Council approved in July 2025, the Middleburg Police chief sets the parade route and has the final say on whether the parade goes on. The Town provides police and staff, and for this year it has budgeted a $12,000 sponsorship, up from $10,000, along with police overtime, officers from other jurisdictions and public works help.

The Rest of December Doesn't Need a Shuttle

Most of Middleburg's other holiday events are smaller, and many are in walking distance for anyone who lives near the village. They also give local shops and restaurants business on days without a 10,000-person crowd.

Week of November 23

• Salamander Middleburg's Santa Experience at its Equestrian Center, Friday, November 27, 9 a.m. to 4 p.m., with a wagon ride to Santa's Workshop. Reservations are required.
• Small Business Saturday, November 28, promoted by the Red Fox Inn & Tavern as a day for more than 100 local boutiques. The Red Fox's holiday carriage rides run weekends through December 28, except parade day.
• The Byrne Gallery's Yuri Gorbachev exhibition, marking the gallery's 30th anniversary, runs November 4 through December 30.

Week of November 30

• Town of Middleburg Tree Lighting at the Pink Box, Friday, December 4. Gates open at 5 p.m. and the lighting is at 5:30 p.m. More than 400 people came to last year's lighting, according to the Eccentric's council report.
• Salamander's Christmas in Middleburg BBQ in the Middleburg Ballroom, December 5, 11 a.m. to 4 p.m., $72 per adult and $30 per child ages 2 to 12. Check with Salamander about access before planning around it.
• Decorate Your Own Gingerbread House at Salamander, Sunday, December 6, at 10 a.m. or 2 p.m.

Week of December 7

• Dickens of a Dog Show at the National Sporting Library & Museum, December 10, per the Red Fox Inn & Tavern's calendar.
• Jingle in the 'Burg on S. Madison Street, Saturday, December 12, 10 a.m. to 4 p.m., with carolers, dancers, actors, musicians and holiday vendors.
• Holiday Afternoon Tea at Harrimans, December 12, 1 to 3 p.m.

Week of December 14

• A Dickens of a Christmas, December 17, with A Christmas Carol, St. George and the Dragon, vendors, storytime at Middleburg Books and the Dickens Dancers.
• Jingle Paws Parade, presented by Tilley's Pet Supplies, Saturday, December 19 at 1 p.m. It starts at the National Sporting Library & Museum, runs through town and ends with a Yappy Hour at Brick & Mortar.
• Santa Brunch in Salamander's Middleburg Ballroom, December 19, 10 a.m. to 2 p.m.

How the Gap Gets Closed

The organizers have money in the bank, but less room than the balance suggests. Their Statement of Financial Position showed $79,180 as of February 23, 2026, with no debts. Michelle Myers said they spend $40,000 to $60,000 in advance payments before parking sales open in September. By the Eccentric's math, that leaves somewhere between $6,000 and $26,000 to absorb a missing $20,000 sponsor. They're already cutting back. "We will move out of our office space at the end of 2026, we will cut back on social outreach and admin support," she said.

At the September meeting, Mayor Bridge Littleton suggested that members of the Middleburg Business and Professional Association each "chip in 200 bucks." The organizers recently added family sponsorships, and they can be reached at [email protected]. "We can take sponsorship help all year round," Michelle Myers said. A $60 parking pass bought by a resident who could have walked in still goes into the same revenue line as everyone else's.

The tradition goes back to 1979, when Mayor Loyal McMillin suggested the town needed a Christmas celebration. In 1980, Dudley and Cissy Bunn and Tyler Gore put together the first modern parade. Jim Herbert made it a nonprofit in 2011. Michelle and Doug Myers started volunteering in 2018 and became its part-time co-organizers in 2022.

At 15 West Homes, we follow Middleburg's calendar the way our neighbors do, from the tree lighting to the last carriage ride. If you own a home within walking distance of Washington Street and want to know what it's worth going into the new year, request your free home valuation.