The Middleburg Community Center at 300 West Washington Street has more on its October calendar than any other address in town. It is the box office for the Middleburg Film Festival. On the festival's first afternoon it shows a film before opening night. It is a stop on the festival shuttle loop. On Halloween it is where the parade lines up. Farther east on the same street, a new Celtic goods shop opened in May. In the 100 block of West Washington, a builder is turning the former Fun Shop into an Italian restaurant and a private club.
Most of the month happens within a few blocks of the street everyone already drives. During festival week, the town also changes its parking rules.
The Community Center carries most of the month
The festival's own FAQ lists four screening venues, and the Community Center is the one that does the most. It sells tickets and hosts the Thursday-afternoon screening before the 7 p.m. opening night at Salamander. Two weeks later, the MBPA and Middleburg Police Department Halloween Parade gathers there at 5 p.m. on Saturday, October 31. The parade goes "through Town," with trick-or-treating at local businesses and with Police Chief Shaun Jones. That same evening, the Community Center hosts Hot Dog It's Halloween. Its own event page lists 5 to 8 p.m., and one Visit Middleburg listing gives 5 to 7 p.m., so check the end time before promising kids a late night.
The National Sporting Library & Museum at 102 The Plains Road is close by, and it carries a similar share of the calendar. On Sunday, October 4, from 2 to 3 p.m., it hosts the Interfaith Blessing of the Animals, rain or shine. Dogs, cats, horses, hounds, livestock, fish and teddy bears are all welcome. It is also a festival venue, and two exhibits run past the end of the season: Pursuits of Independence and the Natural World through December 6, and George Washington and a Nation of Farmers through January 10, 2027.
Festival week changes the parking rules
The Middleburg Film Festival runs October 15 through 18, 2026. Here is how its venues line up:
| Venue | Address | Festival role |
|---|---|---|
| Salamander Resort | 500 North Pendleton St. | Opening night, 7 p.m. Oct. 15 |
| The Hill School | 130 S. Madison St. | Screening venue, shuttle stop |
| Middleburg Community Center | 300 W. Washington St. | Box office, Thursday pre-opening film |
| National Sporting Library & Museum | 102 The Plains Rd. | Screening venue, shared shuttle stop with Community Center |
The festival's FAQ promises free parking at its venues and around town, and free meters on what it calls Main Street, for the length of the festival. Shuttles will run a continuous loop between Festival Headquarters, the Hill School, the Community Center and NSLM, and Salamander. The route and times will be posted closer to the dates. On Friday and Saturday, screenings run from about 9 a.m. to 11 p.m. On Sunday they end around 7 p.m. That makes four days in a row when the town runs close to round the clock.
If you didn't buy a pass over the summer, timing is the main issue. All advance packages are listed as sold out. These include the $2,700 Backstage All-Access Pass, the $1,450 Film Lovers Pass, the $400 Hill School Venue Movies Pass, the $125 Saturday Day @ The Movies Pass and the $150 Future Filmmaker's Pass. The festival says single tickets go on sale at the beginning of October, along with the full slate and schedule. In mid-September, Washingtonian reported that single-ticket prices had not been announced yet.
The first wave of announced films gives a sense of what will be in demand:
- Opening night, October 15: A24's The Debut, followed by a Q&A with writer-director Jesse Eisenberg and star Julianne Moore.
- Saturday centerpiece: I Play Rocky, directed by Peter Farrelly, with Anthony Ippolito as Sylvester Stallone, followed by a Q&A with Jay Duplass and P.J. Byrne.
- Also announced: Gentle Monster, Club Kid, Ink, Wicker and Elsinore.
- Honorees and guests: Léa Seydoux, Jordan Firstman, Jack O'Connell, makeup and hair designer Nadia Stacey, and composer Daniel Pemberton, who will also give a concert. Olivia Colman is a special guest for Wicker and Elsinore.
The weekend before belongs to Glenwood Park and Dresden Farm
The town's October starts out in the fields. The Virginia Fall Races hold their 72nd running on Saturday, October 10, at Glenwood Park, with the first race at 12:30 p.m. General admission is sold per car. The price is $50 from August 31 through race day, by cash at the gate or online. It covers four people, with $10 for each additional person. Reserved spaces are sold out. The 2026 ticket form bans personal tents, canopies and grills, so a tailgate with folding chairs and a cooler is fine, but a shade tent is not. The race organization says it has given to the INOVA Loudoun Hospital Foundation every year since 1955.
The next afternoon is smaller. The 2nd Annual Middleburg Hound Steeplechase runs from 3 to 5 p.m. on Sunday, October 11, at Dresden Farm. The Middleburg Hunt lists the field entrance as 22553 Dresden Farm Lane.
These two days are the start of a five-day lead-in to the festival. One weekend has steeplechase at Glenwood Park, the next has screenings in four venues around town, and the days in between hold the town's own civic dates.
The town-only dates in between
Visitors mostly won't see these dates. They come from the Town's September 2026 memo and Visit Middleburg's October roundup, listed here in order:
- Saturday, October 3: The Red Fox Inn & Tavern lists its Dining Room and Night Fox Pub as closed for the day. Its regular hours resume after that.
- Sunday, October 4: Blessing of the Animals at NSLM, 2 to 3 p.m.
- Wednesday, October 7: Coffee with a Cop.
- Tuesday, October 20: Mayor Bridge Littleton's annual State of the Town address at Town Hall, 6 p.m. It is open for questions and will be livestreamed and recorded on the Town's website.
- Saturday, October 31: Halloween Parade, gathering at the Community Center at 5 p.m.
The same memo has two notes that matter more than any event this month. First, VDOT will pave Route 50 through Middleburg "in the coming weeks," working from 10 p.m. to 5 a.m. Exact dates had not been announced when the memo went out. Second, the Town's mandatory water conservation is still in effect. Outdoor water use is banned, hand watering is allowed only before 9 a.m. and after 6 p.m., and restaurants are not to serve water unless a customer asks. The Town reports a 17 percent drop in average weekly use since the rules began, and says the aquifer still has a ways to go. At a festival-week dinner, ask for water if you want it.
The 100 block is still under construction
The last part of the West Washington story is the slowest. Faire Isles Trading Co. opened at 116 West Washington Street in early May 2026, selling Celtic, Irish and Scottish goods. At 115 and 117 West Washington, the former Fun Shop has been closed since 2023, after 66 years.
Kevin and Remington Ash, the developers behind Hotel Burg in Leesburg, are building three things in that space. The ground floor will be an Italian restaurant called La Caccia, which means "The Hunt," next to the Post Office. A historic house on the property will become an Italian café serving breakfast, lunch and dinner. Behind the café will be a small speakeasy that already has its ABC license. The second floor, the rooftop and the speakeasy will belong to a second location of The Chase Club, the private social club. In July, Clay Construction was working inside on the restaurant, the club and what Kevin Ash calls "two proper bars."
"We wanted a place where we could hang out with our friends and that we built and owned." Remington Ash, to The Middleburg Page, July 2026
The most recent public step came on September 3. That day, the Town's Historic District Review Committee agenda listed a fence request and sign requests for "La Caccia/L'Enoteca/The Chase Club." The project's target is still "this fall," and no opening date has been announced. For festival week, plan on the restaurants that are already open.
The new businesses that have opened are mostly daytime places, a block or two off West Washington. The Clothing Closet, a nonprofit thrift boutique run by Tree of Life Ministries, held its ribbon cutting at 15 E. Federal Street on July 9. It is open Tuesday through Saturday, 10 a.m. to 5 p.m. In September, Revive Clinic and IV Therapy opened at 200 E. Washington Street, and Granted Wellbeing held its grand opening at 11 S. Madison Street.
For a new evening option, head west. Hunter's Head Tavern, at 9048 John S. Mosby Highway in Upperville, was bought in late 2025 by Noel and Alannah Sweeney of Trinity Farm. It reopened after minor renovations, with Middleburg sommelier Jarad Slipp running it. It kept its name and plans a British-pub menu.
If the changes on West Washington Street have you wondering what your own property on or near it is worth right now, The Bill Davis Team can put real numbers on it before La Caccia opens. Request Your Free Home Value Report.
