October Events in Hunt Country: Part 1
Crisp days and colorful landscapes set the scene for a memorable October. From local fairs and festivals to fall wine tastings, countryside traditions, and Halloween celebrations, October offers plenty of reasons to explore. Discover a new favorite outing or revisit a cherished tradition across Northern Virginia, the Eastern Panhandle, and beyond.
I had the honor and joy of emceeing the Corgi Races at the Middleburg Oktoberfest on Saturday, September 19th. This photo perfectly sums up the joy the Corgis, their owners, and the spectators shared. At a time when the world around us seems to be going crazy, simple pleasures like this bring us all together.
The Distinguished Gentleman’s Drive
The Distinguished Gentleman's Drive, postponed from September 27th, took place on Sunday, October 4th, and I had the pleasure of driving a 1966 Rolls-Royce Silver Shadow Two-Door Coupé by James Young (coach builders).
This is for such a good cause - check out the Distinguished Gentleman’s Drive website! Huge thanks to my generous sponsors!
Before the big day, I also took the Rolls and a very nice Jaguar E-Type 4.2 Coupé out for a test drive and made a quick video of my drive through the Virginia countryside!
Our Office's Most Recent Listings
Here are a few of our office's most recent listings. Discover more of our current listings by clicking the "View More Listings" button below. Who knows, you might find one with character as unique as yours.
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
Of course, the best way to know if a home is right for you is to spend time in the community around it. Fall is when Northern Virginia and Hunt Country really come alive, with harvest festivals, small-town traditions and weekend events worth planning around. Here are a few October events in Hunt Country over the next couple of weeks.
October is Virginia Wine Month
Pick a vineyard or a weekend. Plot out the perfect itinerary or follow wherever the road takes you to explore the shifting landscape and extraordinary wines of Virginia.
EVENTS & OFFERINGS
Don't miss the exciting events and specials going on all month long. Discover More
Local & Family Adventures
October brings fresh ways to connect with our communities, from equestrian competitions and historic walking tours to live music, local markets, and downtown gatherings. Explore what's happening across Northern Virginia, the Eastern Panhandle, and nearby destinations.
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
Morven Park International & US Equestrian Open – Morven Park
October 8–11 | 8 AM–5 PM | Leesburg, VA | Watch elite dressage, cross-country, and show jumping, including the U.S. Equestrian Open Eventing Final. Enjoy tailgating, hospitality, food, and a vendor village throughout the grounds. Get Event Details
The writer's eye with Elizabeth Letts – National Sporting Library & Museum
October 8 | 10 AM–1 PM | Middleburg, VA | Author Elizabeth Letts leads an intimate writing workshop, using objects and images from the museum's collections to spark new stories. Space is limited. Learn More
The Virginia fall races – Glenwood Park
October 10 | Middleburg, VA | Bring a picnic for a day of steeplechase racing at Glenwood Park. Learn More
Sacrifices & circumstances – Harpers Ferry National Historical Park
October 10 | 11 AM–4 PM | Harpers Ferry, WV | Explore the people and decisions behind John Brown's 1859 raid. Ranger-led walking tours begin at John Brown's Fort at 11 AM and 3 PM, with an additional program in Arsenal Square at 1 PM. Programs are included with park admission. Get Event Details
Workhouse open house & art walk – Workhouse Arts Center
October 10 | 6–9 PM | Lorton, VA | Spend an evening exploring the studios and art at Workhouse Arts Center. Plan Your Visit
Sunrise sweat with lululemon – One Loudoun Park
October 11 | 9–10:30 AM | Ashburn, VA | Start the morning outdoors with three 30-minute yoga classes at One Loudoun Park. Get Event Details
Youth sports gear swap – Clearbrook Park
October 11 | 1–3 PM | Clear Brook, VA | Families can exchange sports gear at this free community event at Clearbrook Park. Learn More
Sunset in the field – Farmer's Delight
October 11 | 3:30 PM–Sunset | Middleburg, VA | Join the Land Trust of Virginia for an afternoon of live bluegrass, barbecue, local drinks, Blue Ridge views, and activities for children. Get Event Details
The royal gala – Hollywood Casino
October 15 | Social Hour 5:30 PM; Gala 6 PM | Charles Town, WV | Celebrate the region's apple-growing heritage in Hollywood Casino's ballroom. This Mountain State Apple Harvest Festival gathering recognizes the Honored West Virginian and introduces the 2026 Queen Pomona court. Learn More
Ghosts, Gourds & Gatherings
Find your Halloween fun, from haunted trails and corn mazes to spine-tingling walks through historic grounds.
Whether you prefer playful celebrations or an evening of frights, there's plenty to enjoy this October.
Haunted hollow – Maple Tree Farm
Fridays & Saturdays, Sep 25–Oct 31 | Ticket Times Vary | Warrenton, VA
Follow a haunted trail through and around the barns of an abandoned farm. Get Tickets
Fields of fear – Cox Farms
Fridays & Saturdays, Sep 25–Nov 7 & Oct 11 | 7:30–11 PM | Centreville, VA
Explore Cornightmare, The Forest, and the Dark Side Hayride, with entertainment and food at The Firegrounds. 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 15 & 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
Fall Festivals & Seasonal Traditions
Celebrate autumn with pumpkin patches, apple harvests, artisan fairs, and seasonal food and wine. Across the region, fall festivals invite you to spend time outdoors, discover local makers, and enjoy the traditions that make this season special.
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
Washington West Film Festival
Various Venues | October 8–12 | Screening Times Vary | Reston, VA | Attend film screenings and filmmaker conversations at venues around Reston, including LOOK Cinemas at Reston Town Center, in support of local nonprofits. View Festival Details
Mount Vernon Fall Wine Festival
George Washington’s Mount Vernon | October 9–11 | 6–9 PM | Mount Vernon, VA | Sample Virginia wines, take an evening walk through the Mansion, and enjoy sunset at Mount Vernon. Get Tickets
Fairfax Fall Festival
Old Town Fairfax | October 10 | Fairfax, VA | Celebrate the festival’s 50th anniversary with entertainment, hundreds of craft and food vendors, and family activities. Get Event Details
Fall Arts & Crafts Show
Fredericksburg Convention Center | October 10–11 | Time Not Listed | Fredericksburg, VA | Shop handmade jewelry, home décor, artwork, and seasonal gifts from more than 175 makers. Get Event Details
Marker-Miller Orchards Apple Harvest Festival
Marker-Miller Orchards | October 10, 9 AM–5 PM; October 11, Noon–5 PM | Winchester, VA | Celebrate apple season with apples, cider, baked treats, craft vendors, a cow train, and scenic wagon rides around the farm. Plan Your Visit
Parktober Fest
Ellanor C. Lawrence Park | October 10 | Chantilly, VA | Enjoy live music, craft beer, food and artisan vendors, and nature activities for children. Get Event Details
Providence FallFest
Jim Scott Community Center | October 10 | 11 AM–2 PM | Fairfax, VA | Enjoy performances, games, activities for all ages, and county and community resources. Get Event Details
Reston Town Center Rocktoberfest
Town Center Pavilion | October 10 | 5–11 PM | Reston, VA | Hear live sets from Virginia Coalition, Everything, and Vertical Horizon, with Sip & Stroll options nearby. Get Event Details
Pumpkin Picking & Fall Fun
Shawnee Springs Market | October 10, 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
Let's talk
October is one of the best months to see why so many people choose to call this part of Virginia home. If you're thinking about buying or selling in Loudoun, Fauquier, or anywhere in Hunt Country, I'd be glad to talk through what's happening in the market and what it means for you. And watch for Part 2 coming soon, with more events to round out the season.
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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