Late October Events in Hunt Country: Part 2
October saves some of its best for last. The leaves are at their peak, the International Gold Cup returns to Great Meadow, and Halloween parades fill main streets from Leesburg to Middleburg. Here’s your guide to the second half of the month, plus a look at what September’s contracts tell us about the local market.
Fresh from San Francisco
Earlier this month I joined colleagues from around the world at Sotheby’s International Realty’s 2026 Global Networking Event in San Francisco, celebrating the brand’s 50th anniversary.
I was proud to represent Hunt Country Sotheby’s International Realty alongside our broker/owner, our chief operating officer, and several of my Hunt Country colleagues.
I came home with new ideas and new connections. For my clients, that means their Virginia and Delaware properties reach buyers and advisors far beyond our region.
A selection of listings from our office
348 Ebaugh Drive SE, Leesburg
3 beds, 4 baths
2,774 sq ft, 0.06 acres
$699,000
Patricia Gallardo
703-980-4594
281 Train Whistle Terrace SE, Leesburg
3 beds, 4 baths
2,576 sq ft, 0.02 acres
$739,999
Joanna Terrones
703-963-4884
261 Merrifield Lane, Winchester
5 beds, 6 baths
6,342 sq ft, 6.11 acres
$2,200,000
Lisa Behr
540-533-3853 lisa.behr@hcsir.com
17395 Arrowood Place, Round Hill
5 beds, 4 baths
3,375 sq ft, 0.51 acres
$750,000
Sherry Santmyer, 540-431-8101 sherry.santmyer@hcsir.com
Chloe Powell
September Contract Trends
Presented by Vesta Settlements
Beyond understanding the property itself, contract terms offer insight into how buyers and sellers are negotiating.
Vesta Settlements' latest snapshot highlights September trends in financing, seller assistance, and contingencies, including a weekly breakdown for September 21–27. Explore the figures below for a closer look.
Know Your Property
Presented by Vesta Settlements
A property survey can reveal details that matter, from boundary lines to potential encroachments. Vesta Settlements shares why surveys deserve a closer look, with local examples of issues uncovered before and after closing.
Numbers aside, fall is the best time to get to know these communities in person. Here’s a snapshot of more October events in Hunt Country through the end of the month.
Fall Family Fun & Adventures
Not everything this month is about pumpkins and haunted trails. There’s steeplechase racing at Great Meadow, living history at Harpers Ferry, and plenty of small-town gatherings worth a weekend drive.
International Gold Cup – Great Meadow
October 24 | The Plains, VA | Spend a day at Great Meadow watching steeplechase competition at this celebrated fall race. Learn More
October events at the U.S. National Arboretum
Selected Dates in October | Times Vary | Washington, DC | Choose from seasonal programs including bird walks, a moonlight hike, a fall 5K and festival, and a chile pepper festival. Explore the Calendar
Virginia Scenic Railway autumn special
Selected Dates in October | Departure Times Vary | Goshen, VA | Take one of four limited-run train excursions departing Goshen to see fall color across the Shenandoah Valley. Plan Your Ride
Moonlight market – One Loudoun
Fridays Through October 30 | 5–9 PM | Ashburn, VA | Spend a Friday evening shopping from local makers, artists, bakers, and small businesses. The market is free and open to all ages. Plan Your Visit
Clarke County farmers' market
Saturdays Through October | 8 AM–Noon | Berryville, VA | Shop fresh produce, prepared foods, and handmade goods from Clarke County and Shenandoah Valley vendors. Learn More
At all times ready – Harpers Ferry National Historical Park
October 17–18 | 11 AM–4 PM Daily | Harpers Ferry, WV | Experience living-history demonstrations and stories exploring John Brown's raid. Park staff and the U.S. Marine Corps Historical Company interpret the experiences of Marines, local residents, and formerly enslaved people. Programs are included with park admission. Get Event Details
Walk about nothing
October 21 | 6–7:30 PM | Charles Town, WV | Meet at City Hall, 101 East Washington Street, for a relaxed community walk through downtown. Enjoy an evening connecting with neighbors; children and dogs are welcome. Get Event Details
Annandale parade
October 24 | Time Not Listed | Annandale, VA | See marching bands, floats, dancers, and vintage cars along Columbia Pike. Learn More
Fall garage sale – Fredericksburg Convention Center
October 24 | Time Not Listed | Fredericksburg, VA | Browse antiques, collectibles, clothing, furniture, and other finds from hundreds of vendors at the convention center. Get Event Details
Hip after six — candy drop
October 30 | 6–10 PM | Charles Town, WV | Head to North Charles Street in historic downtown for Charles Town Now's October Candy Drop gathering. Get Event Details
Haunted Happenings
Halloween is almost here, and there’s plenty going on. You can catch a costume parade, take a ghost tour through an old downtown, or go trick-or-treating at the park.
If you want a real scare, a few haunted trails are open too.
Haunted hollow – Maple Tree Farm
Fridays & Saturdays, September 25–October 31 | Ticket Times Vary | Warrenton, VA
Follow a haunted trail through and around the barns of an abandoned farm. Get Tickets
Buckland haunted farm
Fridays & Saturdays in October | 7–11 PM | Warrenton, VA
Make your way through a half-mile haunted trail in the corn, then try to escape an inflatable maze. Get Tickets
Milltown haunt
Select Nights, October 2–November 7 | Midway Opens 6 PM; Haunts Open 7 PM | Lovettsville, VA
Explore three indoor and outdoor haunted attractions—Thorne House and Barn of Fears, The Void, and Trickster's Hollow—at a working Loudoun County farm. Get Tickets
Dark encounters – Workhouse Arts Center haunt
Fridays, Saturdays & Select Sundays, October 3–30 | Timed Entry Varies | Lorton, VA
Venture through the grounds of the former Lorton Reformatory for a haunted walk filled with unsettling scenes and unexpected encounters. Get Tickets
Factory of fear: outbreak – ARTfactory
October 22, 7–9 PM; October 16, 17, 23 & 24, 7–10:30 PM | Manassas, VA
Navigate an infected world in search of a cure as ARTfactory's four-floor haunted house transforms into an outbreak scenario. Get Tickets
Halloween on the green – Vienna Town Green
October 17 | 10:30 AM–12:30 PM | Vienna, VA
Enjoy crafts, a live animal show, games, treats, and pumpkin decorating at this free family celebration. Get Event Details
Hauntings 2026 – Loudoun Museum
October 22–24 | Evening Tours; Select a Departure Time When Booking | Leesburg, VA
Walk through historic downtown Leesburg and hear ghost stories and tales of the buildings, cemeteries, and people that shaped the town. Tours begin at the museum; advance tickets are required. Get Tickets
Chocolate boo bash mommy & me sculpting workshop – The Conche
October 24 | 10 AM–Noon | Leesburg, VA
Parents and children create and decorate Halloween-themed chocolate sculptures with guidance from The Conche team. Get Tickets
8th annual Halloween bark bash – One Loudoun
October 24 | Noon–3 PM | Ashburn, VA
Enjoy a pet-focused Halloween festival with a dog costume contest, trick-or-treat trail, adoptable dogs, rescue groups, vendors, and children's activities. Get Event Details
Monster mash – Village at Leesburg
October 24 | 1–5 PM | Leesburg, VA
Celebrate Halloween with professional pumpkin carving, trick-or-treating, costume contests for children and pets, cookie decorating, and face painting. Get Event Details
Ashburn Village Halloween spooktacular – Ashburn Village Sports Pavilion
October 24 | 6–7 PM | Ashburn, VA
Tour the decorated grounds, collect candy, and enjoy a pet costume contest. The event is free for Ashburn Village residents. Get Event Details
Clifton haunted trail
October 24 | 7–10 PM | Clifton, VA
For one night, the wooded trail fills with costumed creatures and Halloween scares, including the trail's take on the Bunnyman legend. Get Tickets
Halloween happenings – Clearbrook Park
October 24 | Time Not Listed | Clear Brook, VA
Families are invited to dress up and trick-or-treat through Clearbrook Park at this Frederick County Parks and Recreation celebration. Get Event Details
Haunting sounds: celebrating autumn and All Hallows' Eve – Happy Retreat
October 25 | 3–4 PM | Charles Town, WV
Get into the Halloween spirit with an eclectic guitar and violin concert featuring Sergey Prokofyev and Jan Knutson in this seasonal Appalachian Chamber Music Festival program. Learn More
70th annual Leesburg Kiwanis Halloween parade
October 28 | 6:30–8 PM | Leesburg, VA
Enjoy a longstanding Leesburg tradition featuring marching bands, community groups, and costumed participants. Get Event Details
Vienna Halloween parade – Maple Avenue
October 28 | 7–9 PM | Vienna, VA
Watch floats, bands, and costumed participants travel along Maple Avenue during this free annual parade. Get Event Details
Middleburg Halloween parade & hot dog it's Halloween – Middleburg Community Center
October 31 | Parade Begins 5 PM; Community Celebration 5–8 PM | Middleburg, VA
Gather in costume for the annual parade, followed by hot dogs and family activities at the community center. The celebration is free. Get Event Details
Harvest festival fly-in – Shannon Airport
October 31 | Time Not Listed | Fredericksburg, VA
Celebrate Halloween with aircraft displays, aviation-themed trick-or-treating, candy drops, and family activities. Learn More
Fall Favorites
From apple festivals to pumpkin patches to chalk art to film screenings, the rest of October has lots of good reasons to get out and enjoy the season.
Carroll County Corn Maze
Carroll County Agricultural Center | Through November 1 | Fridays 6–10 PM; Saturdays 2–10 PM; Sundays Noon–6 PM | Westminster, MD | Navigate the corn maze and enjoy fall activities at the Carroll County Agricultural Center. Plan Your Visit
Great Country Farms Pumpkin Harvest
Great Country Farms | September 19–October 31 | 9 AM–5 PM Daily | Bluemont, VA | Explore the corn maze, pig races, farm market, fresh cider, and seasonal treats during this family-friendly harvest celebration. Get Tickets
Pumpkin Village Fall Fest
Leesburg Animal Park | September 19–November 8 | Hours Vary | Leesburg, VA | Enjoy slides, moon bounces, wagon rides, a petting zoo, pedal carts, a corn bin, and weekend entertainment. Plan Your Visit
Temple Hall Farm Pumpkin Patch & Flower Fields
Temple Hall Farm Regional Park | September 26–November 3 | 9 AM–5 PM Daily; Last Tickets at 4 PM | Leesburg, VA | Pick pumpkins and flowers, enjoy wagon rides, visit farm animals, and explore jumping pillows and hill slides. Admission is $15 on weekends and $12 on weekdays; children younger than 2 enter free. Each paid admission includes one pumpkin and flowers. Plan Your Visit
Pumpkin Picking & Fall Fun
Shawnee Springs Market | October 17 & 24 | 10 AM–4 PM | Winchester, VA | Pick pumpkins and enjoy hayrides, an apple slingshot, and other family activities at the market on Senseny Road. Plan Your Visit
Middleburg Film Festival
October 15–18 | Screening Times Vary | Middleburg, VA | Watch curated narrative and documentary films, including premieres and awards contenders, followed by filmmaker conversations. View Festival Details
Go Outside Festival
October 16, 5–10 PM; October 17, 10 AM–11 PM; October 18, 11 AM–6 PM | Roanoke, VA | Celebrate outdoor recreation and adventure over three days in Virginia’s Blue Ridge. View Festival Details
Celebrate Purcellville Festival
Dillon’s Woods | October 17 | Time Not Listed | Purcellville, VA | Enjoy music, carnival games, children’s activities, food, and community entertainment. Get Event Details
Mountain State Apple Harvest Festival
October 17–18 | Gates Open 9 AM | Martinsburg, WV | Celebrate the region’s agricultural heritage, apple harvest, and community traditions. View Festival Details
ChalkFest
Reston Town Center | October 17 | 10 AM–5 PM | Reston, VA | Watch artists turn Reston Town Center into an outdoor chalk gallery, with music, face painting, and family activities. Attendance is free; competition participation requires advance registration. Get Event Details
Oktoberfest Renaissance Festival
Shipgarten | October 17 | 1–6 PM | McLean, VA | Bavarian and Renaissance traditions meet for jousting, archery, axe throwing, costumes, stein hoisting, food, and beer. Get Event Details
Appalachian Oddities Faire
Near the Clarion, 4330 William L. Wilson Freeway | October 17 | Time Not Yet Confirmed | Harpers Ferry, WV | Discover unusual curiosities, dark art, and folklore-inspired finds. The daytime market is recommended for ages 13 and older; a separately ticketed evening costume ball is for ages 21 and older. Get Event Details
Virginia Film Festival
October 21–25 | Screening Times Vary | Charlottesville, VA | Discover films from around the world, documentaries, independent voices, and conversations presented by the University of Virginia. View Festival Details
Marker-Miller Orchards Pumpkin Festival
Marker-Miller Orchards | October 24 | 9 AM–5 PM | Winchester, VA | Choose or pick a pumpkin, browse craft vendors, and enjoy seasonal bakery treats, a cow train, and wagon rides. Plan Your Visit
Fall Harvest Family Days
George Washington’s Mount Vernon | October 24–25 | 9:30 AM–4:30 PM | Mount Vernon, VA | Explore 18th-century harvest traditions through farm activities, music, and demonstrations. Get Event Details
Asia in a Bite Food Fest
One Loudoun | October 31–November 1 | Check Event Page for Daily Hours | Ashburn, VA | Explore Asian street food, fusion dishes, and sweets from dozens of vendors, alongside merchandise vendors and live DJ music. Admission is free with RSVP. Get Event Details
Let's talk about your property
Every market shift creates opportunity for someone. If you are weighing a purchase or sale in Loudoun, Fauquier, or anywhere in Virginia's hunt country, I would be glad to walk you through what these numbers mean for your specific property.
Peter Leonard-Morgan | REALTOR®
Hunt Country Sotheby's International Realty
4 W. Washington St, PO Box 1033, Middleburg, VA 20118
Associate Broker - licensed in Virginia
Broker of Record - licensed in Delaware
o 540.687.8500 | dir 443.254.5530
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