"They have the numbers. They have the fences. And they are ready to race!" That line comes from the Middleburg Hunt's announcement for Sunday, October 11, and the racers it describes are hounds.
On Saturday, October 10, the 72nd Virginia Fall Races run at Glenwood Park, with the first post at 12:30 p.m. The next afternoon, the Hunt holds its 2nd Annual Middleburg Hound Steeplechase at Dresden Farm. Many people will see these as two separate outings on one calendar. They work better as a single meet. Sunday's event uses Saturday's format, including the race classes, the paddock, the fences and the tailgate. It shrinks the scale, the price and the stakes. Once you see the weekend that way, it's easier to decide how to spend both days.
Saturday Sets the Template
The Virginia Fall Races are sanctioned by the National Steeplechase Association and run for real purses. In 2025, the feature was the $50,000 National Sporting Library & Museum timber stakes. The card also included the $50,000 Will O'Keefe Memorial stakes for three-year-old hurdlers, and Potus won a maiden timber race. Those are 2025 results. As of October 1, the National Steeplechase Association's schedule listed the Virginia Fall Races but had no entries posted yet, so the 2026 card isn't confirmed.
The logistics are set. The 2026 visitor schedule lists gates opening at 10 a.m., racing at 12:30 p.m., and gates closing at 6 p.m. General admission is listed at $50 per vehicle from August 31 through October 11, either in cash at the gate or on TicketLeap. Each additional occupant is $10. The car pass covers parking and admission for four people. TicketLeap adds a $2 service fee and a 3% transaction fee when you buy online. The race's own page lists reserved spaces as sold out, so this year it's general admission or nothing. The early $40 presale ran July 31 through August 30, so it's over.
The money stays fairly local. Event proceeds go to the INOVA Hospital Foundation and the Glenwood Park Trust. Race programs sold on the grounds support Sprout Therapeutic Riding & Education Center. If you buy a program at the rail, the money goes to Sprout.
Don't confuse Glenwood Park with the International Gold Cup. That race runs at the Great Meadow Course in The Plains on October 24 and is a separate meet.
Sunday Copies the Card at Hound Scale
Compare the two cards and you'll see what the Hunt did. The Hound Steeplechase runs four races on a short course: Maiden, Open, Stakes and Grand Champion. Fence heights are set to match the hounds' experience. Maiden and stakes are the same classes that fill a Glenwood Park program. Spectators also pick favorites in the paddock before each race, the same ritual they follow on Saturday.
The prize is where the copy stops. The Hunt says the only prize that matters is bragging rights. Saturday's 2025 feature paid $50,000.
The rest of the pricing follows the same pattern:
| Virginia Fall Races, Sat., Oct. 10 | Hound Steeplechase, Sun., Oct. 11 | |
|---|---|---|
| Venue | Glenwood Park | Dresden Farm, field entrance, 22553 Dresden Farm Lane |
| Gates open | 10 a.m. | 1 p.m. |
| First post | 12:30 p.m. | 3 p.m. |
| Car admission | $50 per vehicle, four occupants | $25 per car, paid at the gate |
| Reserved tailgate | Listed as sold out | $200, by phone at 703.431.0322 |
| Proceeds | INOVA Hospital Foundation, Glenwood Park Trust | All proceeds to the Middleburg Hunt |
Sunday also has its own add-on. The Damsel Derby comes back as a champagne relay, with teams of three ladies entering for $30 per team and drinking from glasses of bubbly. The Hunt sums up the afternoon in one line:
No horses required for this one. Just good friends, fast hounds and an afternoon at Dresden Farm.
The event is in its second year. We couldn't find any published account of the first one, including results, names of winning hounds or attendance, so this year's program is the only record available. If tailgating matters to you, Sunday is the day you can still reserve a spot. The reserved spaces at Glenwood Park are gone, and the Hunt is still taking calls.
Filling the Hours Between Posts
The two days start at different times, so they call for different plans. Saturday's gates open at 10 a.m., which leaves the morning for parking and setting up. Sunday's gates don't open until 1 p.m., which leaves a long late morning free. Several places that opened or reopened this year fit into those gaps.
Saturday morning, in the village. Nido Coffee + Teahouse opened in June at 12 South Pendleton Street, inside the Nature Composed garden. Pablo and Natalia Enriquez run it next to floral designer Jenn Pineau's shop. It serves coffee, tea and local baked goods, and Middleburg Life mentioned pumpkin, maple and cinnamon drinks as possible fall specials. Two Washington Street-area shops are close by. Faire Isles Trading Co. opened in early May at 116 West Washington Street. Owners Adam and Stephanie Shahan stock Irish sweaters, tweed jackets, kilts and tartan goods. A tweed jacket suits a cool October afternoon at the rail. Middleburg Books reopened at 17 South Madison Street on March 5 after a temporary closure caused by a fire, and it came back as a refreshed shop under owner Mary Beth Morell.
Sunday before the 1 p.m. gates. Two kitchens outside the village fit the slow Sunday start. Grayson's opened at Goodstone Inn, 36205 Snake Hill Road, in June 2026. It serves breakfast, lunch, dinner and weekend brunch, with a farm-to-table menu led by Executive Chef Ahmed Ibrahim. Hunter's Head, at 9048 John S. Mosby Highway in nearby Upperville, reopened in March after an ownership transition and renovation. Master sommelier Jarad Slipp runs daily operations. The menu now centers on British classics, including a Sunday roast served all day. A British Sunday roast before a hound race at a hunt-country farm fits the day well.
The Opening That Hasn't Happened Yet
The opening many people expected for this weekend hasn't arrived. In July, The Georgetowner reported that developer Kevin Ash planned to open La Caccia, an Italian restaurant, this fall in the former Fun Shop next to the post office. The plans also include an Italian café, a tucked-away bar, and a members' space for The Chase Club upstairs. La Caccia means "the hunt" in Italian, which suits this weekend.
The town's own records show where the project stood more recently. The September 3 agenda for the Historic District Review Committee lists Ash's request for three projecting signs and two wall signs at 115 West Washington Street, under the names La Caccia, L'Enoteca and The Chase Club. The same agenda lists a fence request for that address. That is the latest official record we found. None of the sources we reviewed give an opening date or name a chef. Don't plan race-weekend dinner around 115 West Washington Street yet.
After the Hounds
The rest of October in the village is already scheduled. The Middleburg Film Festival runs October 15 to 18. The Halloween parade starts at 5 p.m. on October 31 at the Community Center, and the celebration there continues until 8 p.m. After that, the Hunt's calendar moves to its own traditions. Junior Day is on November 3, and the Christmas Hunt Parade comes through town at 11 a.m. on Saturday, December 5. Adults in that parade are required to wear formal hunt attire, and the horses are braided.
For the weekend itself, bring $50 in cash for the Glenwood Park gate on Saturday and $25 for Dresden Farm on Sunday. Call 703.431.0322 before Sunday if you want a reserved tailgate spot.
If the slower pace of a Middleburg October has you thinking about what a place in hunt country could look like for you, Rachel Van Zanten knows the land, the farms and the roads between Glenwood Park and Dresden Farm, and would be glad to talk it through quietly. Let's Connect.
