Fall Events in Loudoun County 2025: A Local Guide to Autumn Adventures
If you're a longtime resident, or just considering buying a home in Loudoun County, this region is really at its best in the autumn months.
Here are some upcoming fall 2025 events that showcase why so many families work with our top Loudoun County real estate agents to make this area home.
Harvest Festivals and Fall Celebrations in Loudoun County
This section covers the best seasonal festivals and celebrations happening throughout Loudoun County this fall, from wine tastings to traditional harvest events.
August & September Events:
- LoCo Fest 2025 – August 31 at 868 Estate Vineyards in Purcellville featuring over 20 bands across multiple genres, local wines, craft beers, and food vendors
- Crossroads Music Festival 2025 – September 19-20 at Tally Ho Theatre with headliners Sister Hazel and Andy Summers (legendary guitarist of The Police)
- Middleburg Oktoberfest – September 20, 11 AM-6 PM with two biergartens, traditional German food, live music, German dancers, and Corgi dog races
- Oktoberfest at Dirt Farm Brewing – September 20, 12-7 PM in Bluemont with German-inspired beer and food specials
- Oktoberfest at Solace Brewing Co. – September 20, 11 AM-10 PM in Sterling featuring Festbier release, live music with Hot Taters, and Oktoberfest trivia
- Larktoberfest 2025 – September 27, 11 AM-10 PM at Lark Brewing Co. in Aldie with seasonal beers, live music, German dancers, face painting, and 21+ beer garden
- LoCo Wine Festival – September 27-28 at Old Farm Winery where 14 Loudoun wineries serve tastings in a refurbished timber barn with live bands performing
- Leesburg Airshow – September 27, 11 AM-4 PM featuring antique and modern planes, the Douglas C-54 Skymaster “Spirit of Freedom,” and Smithsonian demonstrations
October Events:
- 37th Annual Leesburg Car Show – October 4, 12-4 PM in historic downtown Leesburg with over 150 classic, street rod, muscle, custom, and sports cars (free admission)
- 81st Annual Waterford Fair – October 3-5 in historic Waterford featuring colonial-era arts, crafts, music, and private home tours of 18th-century preserved homes
- Morven Park International & Fall Horse Trials – October 9-12 with $200,000 prize money, televised on ESPN3, featuring world-class riders competing for 2028 Los Angeles Olympics qualification
- Celebrate Purcellville Fall Festival – October 18, 2-5 PM in Dillon’s Woods with carnival games, obstacle course, live music, and food vendors
- Loudoun Fall Farm Tour – October 18-19 with more than 30 participating farms showcasing locally grown produce, farm animals, and meet-the-farmer experiences
- Sunset in the Field 2025 – October 19, 3:30-7 PM in Middleburg featuring Lonesome River Band, bluegrass music, BBQ, and Blue Ridge Mountain sunset views ($110 admission)
November Events:
- Purcellville Artisan Tour – November 1-2, 11 AM-5 PM featuring local artisans, demonstrations, tours, and pre-holiday sales at 13 locations including 868 Estate Vineyards
- Cakechella 2025 – November 9, 1-5 PM at Bluemont Station Brewery & Winery, a dessert-tasting festival with live demos and sweet treats ($20 adults, $10 kids)
- Ciders & Sides Friendsgiving – November 14, 6:30-8:30 PM at Henway Hard Cider with five-course meal paired with seasonal ciders ($55 per guest)
- Seventh Annual Dirt Farm Christmas Market – November 30, 11 AM-4 PM featuring handmade items from local artisans, holiday beverages, and unique gift shopping
Family-Friendly Fall Activities: Pumpkin Patches and Corn Mazes in Loudoun County
Families will find endless autumn adventures with pumpkin picking, corn mazes, and seasonal activities designed for all ages throughout Loudoun County.
Great Country Farms – Bluemont (Main Fall Destination):
- Corn Maze & Apple Harvest – August 30-September 30, 9 AM-5 PM daily
- Weekday advance: $12/child, $14/adult
- Weekend advance: $14/child, $16/adult
- Apple picking, fresh cider tasting, corn maze, giant slides, jumping pillows, Farm Ninja obstacle course
- Family Flashlight Corn Maze Nights – September 20 & 27, 6-8:30 PM
- Advanced tickets: $10/child, $12/adult
- Includes bonfire marshmallow roasting, farm animals visits, glow cart shopping
- Farm market with kettle corn, apple cider donuts, and pies
- Pumpkin Chunkin’ – November 1-4, 9 AM-5 PM
- Advance: $10/child, $12/adult
- Silo Drop, Zip Wire Sploosh, 40-foot Pumpkin Drop Zone
- Marshmallow roasting 11 AM-4 PM weekends
- Pumpkin “Wall of Death” smashing station
Other Family Farm Experiences:
- Leesburg Animal Park Pumpkin Village – September 21-November 5
- 25th anniversary celebration with exotic animals
- Giant hill slides, moon bounces, wagon rides, petting zoo, pedal carts, pony rides
- Weekend features: live music, face painting, fresh harvest treats, kiddie zipline
- Temple Hall Farm Pumpkin Patch – September 27-November 2
- Wagon rides through 286-acre farm
- Pumpkin picking and sunflower gathering for holiday décor
- Giant jumping pillows, farm animal scavenger hunt, corn box play area
- Proceeds from sunflowers benefit apprenticeship program for neurodivergent individuals at Legacy Farms
Additional Fall Activities:
- Nomini Bay Oyster Festival – Multiple weekends (9/6-7, 10/4-5, 11/1-2, 12/6-7) at Dirt Farm Brewing
- Virginia-grown oysters served raw and grilled
- 12-5 PM outdoor events
- Hail to the Trail Green Expo – September 28, 1-4 PM in Purcellville
- Free family event at Chapman DeMary Trail
- Tree planting, live animals, environmental activities, live music
- Explores 10-acre old-growth forest area
Northern VA Fall Foliage and Nature Adventures
Discover where to see the most spectacular autumn colors and enjoy outdoor activities in Loudoun County’s stunning natural areas and nearby regional parks.
Loudoun County Scenic Drives & Local Parks:
- Hunt Country Scenic Drive – Winding route through Loudoun and Fauquier Counties
- Rolling hills, vineyards, historic horse farms
- Peak foliage typically mid-October
- Countless photography opportunities and peaceful driving
- Banshee Reeks Nature Preserve – Leesburg location with hiking trails and historical significance
- Ball’s Bluff Battlefield Regional Park – Local hiking with Civil War history and autumn scenery
- Appalachian Trail at Bears Den Trail Center – Bluemont access to renowned fall hiking experiences
Regional Virginia State Parks:
- Sky Meadows State Park – Delaplane location offering spectacular fall vistas
- Endless trails and picnicking opportunities
- Piedmont Overlook Trail – Family-friendly hiking through meadows, forests, and streams with countryside views
- Raven Rocks Trail – Bluemont area, moderate 5.5-mile hike
- Breathtaking overlooks of Shenandoah Valley and Blue Ridge mountains
- Challenging adventure with rewarding fall foliage views
Nearby Lake and Water Areas:
- Lake Thoreau and Lake Audubon – Reston area with tree-lined walking paths
- Benches for enjoying mirrored reflections of autumn leaves
- Some of the earliest and most photogenic fall foliage
- Burke Lake Park – Fairfax County’s largest lake with 5-mile loop trail
- Pretty water views combined with vibrant fall colors
- Wide, level paths suitable for families
Premier Northern Virginia Fall Destinations:
- Great Falls Park – Dramatic waterfall views surrounded by changing leaves
- Top destination for fall picnicking and hiking
- Mather Gorge Trail – Moderate difficulty with spectacular Potomac River views
- Multiple trails offering different waterfall perspectives
- Local Vineyards – Throughout Loudoun County
- Combine fall foliage viewing with wine tasting experiences
- Rolling hills burst with color during peak season
- Perfect autumn day trip destinations
Peak Foliage Timing:
- Early October – Lakes and water areas show first dramatic colors
- Mid-October – Peak foliage season throughout most of region
- Late October – Mountain overlooks and higher elevations reach peak
Explore more parks for fall foliage in our blog post: The Best Local Hikes in Northern Virginia in the Fall – Garrell Real Estate
If you’re exploring these natural wonders as a visitor or resident, Loudoun County’s combination of accessibility to outdoor recreation and desirable communities explains why so many people work with our team of top Loudoun real estate agents to make this area their home.
Make Loudoun County Your Home This Fall
Fall in Loudoun County really shows you what makes this area so special. You’ve got world-class wineries, family farms, beautiful natural areas, and community celebrations that bring everyone together. After checking out events like the LoCo Wine Festival, picking pumpkins at Great Country Farms, or hiking in Sky Meadows State Park, you’ll understand why Loudoun consistently ranks as one of Northern Virginia’s most desirable places to live.
Ready to find your dream home here? Contact us today to learn more about available properties and discover the perfect place where you can enjoy all these amazing fall traditions for years to come. Our team specializes in helping families find homes in Loudoun’s most sought-after communities, from Ashburn to Leesburg and beyond.
Looking to buy your first home? Check out our buyer resources. Ready to sell? We’ve got seller resources and a free home valuation to help you get started. We’re here to make your Loudoun County real estate dreams happen.
Best Loudoun County Real Estate Agents
Following these steps, you can increase the value of your property ahead of a home sale, without breaking the bank. Why not start making improvements today! Your home will thank you for it. In the meantime, if you are thinking about selling your home or have any questions, please don’t hesitate to contact us. We’re always happy to hear from you.
