A JOY IN NOVA GUIDE 🌐 JoyInNova.com β“• facebook.com/joyinnova
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Fall Finds

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IN NOVA
πŸ‚ Things to do with kids & family πŸ‚

Your Guide to the
Best of Fall in NOVA!

From fall festivals and pumpkin patches to concerts, markets, outdoor fun and cozy family activities, find it all right here.

Make memories this season!
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🍁 FALL HIGHLIGHTS & COMMUNITY PICKS

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🍁 EXPLORE FALL IN NOVA 🍁

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πŸ‚ 111 things to do this fall πŸ‚
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πŸ—ΊοΈ On the Map

Everything, Plotted

A real, zoomable map with every farm, festival, race and foliage stop in this guide. Click a pin for details and directions. Use the category toggles here, then use the county and week filters directly below the map to narrow the list.

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Charity & Fundraising(8)

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Fundraisers and community causes worth showing up for this fall.

SEP28
LoudounMon, Sept 28, 2026 Β· 9am (8am check-in)

Driving Out Hunger β€” Fore the Kids Golf Tournament

Stoneleigh Golf & Country Club, Round Hill

A charity golf tournament benefiting the Backpack Buddies Foundation of Loudoun, which sends food home with local kids facing hunger over the weekend. Sponsorship and foursome tiers available.

OCT17
LoudounSat, Oct 17, 2026 Β· 10am–5pm

Fall Festival by Joshua's Hands

Hamilton, VA

A free community festival honoring the memory of Joshua Guthrie, celebrating America's 250th this year β€” hayrides, pony rides, a petting farm, crafts, carnival-style games (everyone wins a prize!), an old-fashioned spelling bee, live entertainment, music bingo and an obstacle course, plus a 2pm charity auction supporting Joshua's Hands' volunteer and service programs. Free admission; donations welcome, and volunteer opportunities are available.

SEP5–6
LoudounSat–Sun, Sep 5–6, 2026

September UpDog Challenge

A Click Above, Leesburg

A dog agility competition at the region's premier performance-dog training facility β€” fun to watch even if you're not entering a dog.

SEP11
FrederickFri, Sep 11, 2026 Β· 4pm

Heroes and Harvest Festival

Newtown Commons, Stephens City

A veteran and community resource fair paired with harvest-season festivities on Stephens City's town common.

OCT4
LoudounSun, Oct 4, 2026 Β· 1:30–3:30pm

Blossoming β€” 45 Years of Teaching

Franklin Park Arts Center, Purcellville

A classical Indian dance performance from Konark Dance School & Jayantika Dance Company, marking 45 years of teaching. $20 tickets benefit MKK-USA.

SEP12
FairfaxSat, Sep 12, 2026 Β· 9:30am–2pm

Basset Hound Rescue Fall Festival

Fairfax County

Meet adorable basset hounds and support a good cause while enjoying games, raffles, and pet-friendly activities. Bring the family β€” and your pup!

SEP2
FairfaxWed, Sep 2, 2026 Β· 5pm

Pups in the Pavilion

11900 Market St, Reston

A community dog-friendly evening at Reston Town Center's pavilion β€” meet local rescue pups and support the cause.

SEP20
LoudounSun, Sep 20, 2026 Β· 1pm

Paws & Pours: Dog Adoption Event

14001 Harpers Ferry Rd, Hillsboro

Meet adoptable dogs from local rescues while enjoying drinks and community vendors.

🌾 U-Pick & Harvest

Pumpkin Patches, Corn Mazes & Farms(29)

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The region's big harvest-season farms β€” hayrides, corn mazes, cider, and enough pumpkins for everyone.

SEP19
FairfaxSept 19 – Nov 8, 2026

Cox Farms Fall Festival

Centreville, VA

Giant slides, world-famous hayrides, the Cornundrum corn maze, goat village, live music daily, and a pumpkin to take home. Sept/Oct hours 10am–6pm (last entry 5pm); November 10am–5pm (last entry 4pm). Tickets required, sell out on busy dates.

SEP1–18
LoudounSep 1–18, 2026 Β· Daily 9am–5pm

Apple Harvest + Corn Maze & Pig Races

Great Country Farms, Bluemont

Kick off September with the farm’s 1.5-acre corn maze, apple harvest activities, cider pressing, cider donuts and farm attractions. Apple picking is limited in 2026 because of the April freeze, so check what’s currently available before visiting.

SEP19
LoudounSep 19 – Oct 31, 2026 Β· Daily 9am–5pm

Great Country Farms β€” Pumpkin Harvest Festival & Corn Maze

Bluemont, VA

Pick pumpkins from the patch, explore the corn maze, roast marshmallows and enjoy cider donuts. Weekend pig races run at 11am, 1pm and 3pm. Pumpkins are sold separately.

SEP19
LoudounSept 19 & 26, 2026 (evenings)

Family Flashlight Corn Maze Nights

Great Country Farms, Bluemont

Challenge the corn maze after dark with flashlights, then roast marshmallows on the bonfire.

NOV5–6
LoudounThu–Fri, Nov 5–6, 2026

Pumpkin Chuckin' Festival

Great Country Farms, Bluemont

Great Country Farms' end-of-season send-off for leftover gourds β€” launch pumpkins and close out the harvest.

NOV15
LoudounSat, Nov 15, 2026 Β· 12–5pm

LoCo Cider Fest

Great Country Farms, Bluemont

Kicks off Virginia Cider Week β€” small-batch hard cider tastings from Loudoun-area producers, live music, a local-vendor market, and full run of the farm. 21+ tastings; non-alcoholic option for kids.

SEP5
FrederickSat, Sept 5, 2026 Β· 9am–5pm

Honeycrisp Festival

Marker-Miller Orchards Farm Market, Stephens City

First Annual Honeycrisp Festival β€” a full day dedicated to one of everyone's favorite apples, plus the farm's usual fresh produce, bakery goods, and fudge. Note: an April freeze damaged most of the farm's apple crop this year, so there's no pick-your-own from the trees β€” apples will be available by the bin in the orchard on weekends starting in September.

OCT10–11
FrederickSat–Sun, Oct 10–11, 2026 Β· Sat 9am–5pm Β· Sun 12–5pm

Apple Harvest Festival

Marker-Miller Orchards Farm Market, Stephens City

A weekend celebrating apples with multiple varieties in the farm market, apple cobbler, cider, pies, turnovers, apple pie ice cream and cider donuts, plus vendors, food, cow train rides and scenic wagon rides. Apple availability is limited this year after the April freeze, so check the orchard’s current picking update before visiting.

OCT24
FrederickSat, Oct 24, 2026 Β· 9am–5pm

Marker-Miller Orchards Pumpkin Festival

Marker-Miller Orchards Farm Market, Winchester

Choose pumpkins, enjoy pumpkin treats from the bakery, browse vendors, grab food and let the kids ride the cow train. Scenic wagon rides are also planned during the festival.

OCT3
πŸ“ Beyond (WV)Sat, Oct 3, 2026 Β· 9am–3pm (raindate Oct 4)

Farm-mooo-za

Schildt Family Farm, Falling Waters, WV

Just across the state line from Frederick County β€” a fall farm day worth the short drive. Confirm hours and activities directly with the farm before you go.

NOV20
ClarkeWeekends, mid-Sept–early Nov 2026 (confirm exact dates)

Wayside Farm Fun β€” Fall Festival

Berryville, VA

A 120-acre working farm off Route 7 with a 10-acre corn maze, 8-acre u-pick pumpkin patch, pig races, hayrides, farm slides and a jumping pillow. 2026 season dates weren't posted yet as of this check β€” the farm's site says they're "busy planning" for fall.

NOV20
LoudounWeekends, mid-Sept–early Nov 2026 (confirm exact dates)

Pumpkin Village β€” Leesburg Animal Park

Leesburg, VA

20+ acres of fall fun at the animal park β€” giant hill slides, a zip line, pedal carts, wagon rides, moon bounces, live music weekends, plus camels, zebras, lemurs and more. 2026 dates hadn't posted yet as of this check; runs roughly late Sept through early Nov most years.

FALL2026
LoudounSeasonal, fall 2026 (check NOVA Parks week)

Temple Hall Farm β€” Pumpkin Patch & Sunflower Fields

Temple Hall Farm Regional Park, Leesburg

A NOVA Parks property β€” pick your own pumpkins and sunflowers, wagon rides, farm animals, and jumping pillows on a working regional-park farm.

OCT20
FauquierWeekends, October 2026 Β· 10am–4pm

Maple Tree Farm β€” Fall Pumpkin Festival

Warrenton, VA

Pumpkins, a corn maze, train rides, farm animals and puppet shows on a family-run farm just outside town β€” confirmed open weekends throughout October 2026 per the farm's own site.

OCT20
FauquierWeekends through October 2026 (confirm exact dates)

Messick's Farm Market β€” Fall Festival

Bealeton, VA

Hayrides, a corn maze, zip line, candy cannon, bounce pillow and a u-pick pumpkin patch at this family-owned farm market, alongside their farm-fresh food and frozen custard.

SEP20
πŸ“ Beyond (MD)Sept 20 – Nov 1, 2026 Β· Wed–Sun

Butler's Orchard β€” Pumpkin Festival

Germantown, MD

A DC-area institution and one of the region's biggest pumpkin festivals β€” hayrides, corn maze, giant slides, a rubber duckie derby, and 300 acres of pick-your-own. About 45 minutes from Dulles-area Loudoun.

OCT17–18
LoudounSat–Sun, Oct 17–18, 2026

A Decade of Ponies β€” A Mountain of Memories

Hogback Mountain Pony Rides, Leesburg

Ten years of hand-led pony rides β€” a family-run, teacher-owned operation known for being especially good with kids. A milestone-anniversary weekend event.

SEP6
LoudounSun, Sep 6, 2026 Β· 11am

NOVA Fruit Festival 2026

Planetary Farms, Purcellville/Hillsboro

Meet the growers behind 400+ varieties of fruits, vegetables, nuts and edible plants, including a geothermal greenhouse full of tropical fruit trees you won't see anywhere else in the region.

OCT2–3
πŸ“ Beyond (WV)Fri–Sat, Oct 2–3, 2026

Fall Harvest Weekend

343 Campground Rd, Harpers Ferry, WV

A weekend of harvest-season activities just across the state line β€” confirm hours and activities directly with the venue before you go.

SEP12
FrederickSat, Sep 12, 2026 Β· 10am

Sunflower Festival

2502 N. Frederick Pike, Winchester

A field of blooming sunflowers open for photos and picking, alongside the farm's usual fresh produce and fall treats.

OCT24
FrederickSat, Oct 24, 2026 Β· 10am

Homestead Harvest Festival

Fruit Hill Orchard, Winchester

A big, well-loved harvest festival at a working orchard β€” one of the most popular fall gatherings in the area.

SEP5
ClarkeSat, Sep 5, 2026 Β· 1pm

Baby Goat Snuggles

1829 Withers Larue Rd, Berryville

Exactly what it sounds like β€” a hands-on afternoon with baby goats on a Clarke County farm. A guaranteed hit with young kids.

OCT10
FrederickSat, Oct 10, 2026 Β· 2pm

Harvest Festival

333 Jeremiah Lane, Clearbrook

A family-friendly harvest celebration with hayrides, s'mores, hot chocolate, and fall games.

OCT9
FrederickFri, Oct 9, 2026 Β· 7pm

Succulent Pumpkin Workshop

6521 Holter Rd, Middletown

A hands-on workshop planting succulents into mini pumpkins β€” a cute, low-key fall craft night.

SEP10–12
ClarkeThu–Sat, Sep 10–12, 2026

Watermelon Pickers' Fest

Clarke County Ruritan Fairgrounds, Berryville

A community farm festival at the Ruritan Fairgrounds, wrapping up the last of the summer produce season.

OCT31
πŸ“ Beyond (WV)Sat, Oct 31, 2026 Β· 6am

Annual Apple Butter Festival

Shepherdstown Fire Dept, WV

A long-running fall tradition just across the state line β€” apple butter made the old-fashioned way, plus vendors and community food.

NOV21
LoudounSat, Nov 21, 2026 Β· 10am–12:30pm

Fall Festival Fun

Douglass Community Center, Leesburg

Moon bounces, bouncing animals, games, crafts, music and autumn-themed adventures β€” including a visit from Mr. Turkey. Parents don't pay.

OCT24–25
FairfaxSat–Sun, Oct 24–25, 2026

Mount Vernon Fall Harvest Festival

George Washington's Mount Vernon

Celebrate the crisp autumn season with 18th-century activities and demonstrations at the Farm at Mount Vernon.

SEP20
FrederickSat–Sun, Sept 20 – Nov 1, 2026 Β· 10am–5pm

The Pumpkin Patch at Hill High Farm

933 Barley Ln, Winchester

A working Century Farm with pick-your-own apples, a hayride out to the pumpkin patch, an 8-acre corn maze, and antique farm equipment on display. Free to visit; corn maze and hayride ticketed separately.

SEP12
FairfaxSat, Sep 12, 2026 Β· 7am

Ramble 2026

Frying Pan Farm Park, Herndon

A morning ramble through the historic working farm at Frying Pan Park β€” animals, gardens and open fields to explore.

SEP26
πŸ“ Beyond (MD)Sat, Sep 26, 2026 Β· 10am

2026 Fall Festival at Magnolia Meadow Farms

13001 Creagerstown Rd, Thurmont, MD

A fall festival at a working farm β€” hayrides, farm animals, and pumpkins in a picturesque country setting.

πŸ‚ Main Street & Fairgrounds

Fall Festivals & Craft Shows(50)

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Historic villages, town Main Streets, and county fairgrounds turned into juried craft markets and harvest festivals.

OCT2–4
LoudounOct 2–4, 2026 Β· 10am–5pm

Waterford Fair

Waterford, VA

The mid-Atlantic's quintessential fall craft fair β€” 85+ juried heritage and contemporary artisans exhibiting in the National Historic Landmark village, plus home tours, live old-time music, and a wine & beer garden. 82nd annual.

OCT3
FauquierSat, Oct 3, 2026 Β· 9am–3pm

Old Town Warrenton Fall Festival

Warrenton, VA

The 47th annual festival β€” Main Street fills with 160+ booths of handmade goods, artisan crafts, live music and food. One of the top 20 events in the Southeast, drawing up to 25,000 visitors.

SEP19–20
FrederickSat–Sun, Sept 19–20, 2026

Shenandoah Valley Apple Harvest Festival

Clear Brook, VA (Frederick County Fairgrounds)

Over 50 years running β€” local and regional artisans across two open-air buildings, a Kidzone, apple pie baking & eating contests, a classic car show, and a "Tap & Cork" craft beer/cider section. Pet-friendly.

OCT3
LoudounSat, Oct 3, 2026 Β· 12–6pm

BRAMtoberfest

Brambleton Town Center, Ashburn

An Oktoberfest-style fall celebration β€” live music, food and drink vendors, and family activities in the town square.

OCT16–18
ClarkeFri–Sun, Oct 16–18, 2026

Lucketts Fall Market

Clarke County Fairgrounds, Berryville

200+ "vintage hip" vendors β€” antiques, repurposed furniture and one-of-a-kind design finds β€” now in its 25th year. Live music and beer garden on-site.

OCT3
LoudounSat, Oct 3, 2026 Β· 9am–noon

Fall Shred

South Riding Center, Chantilly

Free community document-shredding event at South Riding Center β€” shred only, no electronics or donations accepted.

OCT3–4
FauquierOct 3–4, 2026

Art in the Plains (Grace Episcopal Church Art Show)

The Plains, VA

77th anniversary of this juried regional art show β€” nearly 100 local artists, 300 original works, live music, food trucks and wine tastings on the church green Saturday; show continues Sunday 12–4pm.

SEP19–20
FauquierSat–Sun, Sept 19–20, 2026

Flying Circus Hot Air Balloon Festival

Bealeton, VA

The Flying Circus Aerodrome's annual balloon festival β€” weather-dependent morning and evening hot air balloon launches both days, plus their regular afternoon airshow (biplane barnstorming, wing walking, aerobatics). Suitable for all ages.

SEP19
LoudounSat, Sept 19, 2026 Β· 10:30am

National Jelly Roll Day Sew-along

Webfabrics, Purcellville

A day of sewing, community, and jelly-roll inspiration in the Learning Loft at Webfabrics β€” bring a machine and your own project, or pick up a bundle from the shop. Beginners welcome.

SEP26
LoudounSat, Sept 26, 2026 Β· 11am

3rd Annual Paws N' Pumpkins

Bluemont Station Brewery & Winery, Bluemont

A free, dog-friendly community day hosted by Ridgeside K9 β€” live music, local vendors, food and drink, and pet-friendly activities in a beautiful outdoor setting.

OCT16
FairfaxNow through Oct 16, 2026

Family Movie Night β€” PenFed Plaza

Tysons Corner Center, Tysons

Free outdoor movie screenings on PenFed Plaza β€” bring a folding chair and blanket for family-friendly films under the stars.

JAN1
FairfaxNow through Jan 1, 2027

Fairfax County LEGO Exhibit

Tysons Corner Center, Tysons

An immersive LEGO installation celebrating Fairfax County's 250th anniversary β€” free, indoor, spans the whole fall season.

OCT17
LoudounSat, Oct 17, 2026 Β· 10am–5pm

Fall Festival by Joshua's Hands

Hamilton, VA

A beloved Loudoun tradition celebrating America's 250th this year β€” free family festival with hayrides, pony rides, carnival-style games, a petting farm, crafts, live entertainment, music bingo and an obstacle course. Also benefits Joshua's Hands' charity work (see the Charity section above).

SEP19
FairfaxSat, Sep 19, 2026 Β· 12pm

Oktoberfest

43055 Center St, Chantilly

A family-friendly Oktoberfest with Kiddie Academy on board for kids' activities alongside the usual German food and beer-garden atmosphere.

OCT10
πŸ“ Beyond (Warren Co.)Sat, Oct 10, 2026 Β· 10am

The 54th Annual Festival of Leaves

Downtown Front Royal

One of the region's biggest and longest-running fall festivals β€” worth the drive out to Front Royal for the full downtown-takeover experience.

SEP25–27
πŸ“ Beyond (WV)Fri–Sun, Sep 25–27, 2026

50th Mountain Heritage Arts & Crafts Festival

1707 Old Leetown Pike, Kearneysville, WV

A major milestone year for this long-running craft festival β€” worth the trip across the state line for the 50th anniversary.

NOV14
πŸ“ Beyond (MD)Sat, Nov 14, 2026 Β· 11am

Quad State Holiday Pickle Fest

Washington County Agricultural Center, Boonsboro Rd, Hagerstown, MD

A National Pickle Day celebration drawing visitors from four states β€” a quirky, food-forward pick if you're up for a slightly longer drive.

SEP26
LoudounSat, Sep 26, 2026 Β· 11am

Nature Bobsledding

Hal and Bernie Hanson Regional Park, Aldie

A dry-land bobsled-style ride through the woods β€” a fun, unusual family outing. Ages 8+, $15.

SEP5
ClarkeSat, Sep 5, 2026 Β· 9am

Wildfest 2026

Seven Bends Nursery, Berryville

A native-plant nursery's community festival β€” hands-on activities, local food vendors and a chance to learn about native landscaping.

FALL2026
FauquierSundays, May–Oct Β· 10am–3pm

Archwood Green Barns Farmers' Market

The Plains, VA

A historic restored horse barn turned weekly market β€” up to 40 local farmers and artisans, indoor and outdoor, rain or shine.

SEP26
LoudounSat, Sept 26, 2026 Β· 10am–5pm

Lovettsville Oktoberfest

Downtown Lovettsville (Zoldos Square)

The 30th annual Lovettsville Oktoberfest returns to its roots this year β€” moved into the historic downtown for a walkable, community-centered celebration of the town's German heritage. Stein hauling, stein hoisting, the famous wiener dog races, live German entertainment, and a kinderfest for the kids. Dog-friendly, rain or shine.

SEP5
FrederickSat, Sep 5, 2026 Β· 7pm

Stampede Rodeo & Bullriding

Stonewall District Ruritan, Clearbrook

A real rodeo β€” bull riding and Western-style entertainment for the whole family. Draws a big crowd every year.

SEP12
FrederickSat, Sep 12, 2026 Β· 9am

3rd Annual Fast & Furious Autos (FFA) Car Show

BriedΓ© Family Vineyards, Winchester

A family car show at a working vineyard β€” classic and custom cars on display, plus the vineyard's usual food and drink.

OCT17
FairfaxSat, Oct 17, 2026 Β· 10am

Centreville Day

5714 Mt. Gilead Rd, Centreville

Centreville's annual community festival β€” vendors, food, live entertainment and family activities on the town green.

SEP7
LoudounMon, Sep 7, 2026 Β· 11am–3pm

LoCo/PRCS Kids Fest

Segra Field, Leesburg

Loudoun County's award-winning Labor Day tradition β€” a free, full day of family-friendly activities for kids of all ages.

SEP19–20
LoudounSat–Sun, Sep 19–20, 2026 Β· 10am–5pm

Bluemont Fair (56th Annual)

Bluemont Community Center

Breathe in some mountain air, shop craft vendors, and get an early start on the holiday gift list. $10 admission, children 9 and under free.

OCT3
LoudounSat, Oct 3, 2026 Β· 12–5pm

Douglass Legacy Day

Douglass Community Center, Leesburg

A free community celebration honoring the history, impact and enduring legacy of Douglass High School β€” Loudoun County's first and only Black high school, 1941–1968. Live entertainment, food trucks, vendors and educational experiences.

SEP19–20
FairfaxSat–Sun, Sep 19–20, 2026 Β· 9am–5pm

Colonial Market & Fair

George Washington's Mount Vernon

Step back in time β€” colonial-attired artisans demonstrate 18th-century crafts, live period music, and 18th-century games on the 12-acre field. Adults $30, youth 6–11 $16, under 6 free.

SEP17
LoudounStarts Thu, Sep 17, 2026 (runs ~2 weeks)

Venardos Circus

Loudoun Station, Ashburn

Broadway-style, animal-free circus under the big top β€” aerialists, jugglers, acrobats and comedy performers backed by an original score. Founded by former Ringling Bros. ringmaster Kevin Venardos. Ticketed.

SEP26–27
FairfaxSat–Sun, Sep 26–27, 2026 Β· 11am–6pm

Mosaic Fall Festival

Mosaic District, Fairfax

A weekend of family-friendly fun with over 90 handmade and vintage vendors, live music and performances, a Kids' Zone, and pumpkin painting.

SEP26
FairfaxSat, Sep 26, 2026 Β· 10am–2pm

Bug Fest

Lake Accotink Park, Springfield

Get up close with the creepy and crawly world of insects β€” hands-on learning, games, and bug-themed fun for the whole family.

OCT3
FairfaxSat, Oct 3, 2026 Β· 11am–7pm

Vienna Oktoberfest

Historic Church Street, Vienna

Beer, wine, food, music, vendors and kids' activities on historic Church Street. Free admission.

OCT10
FairfaxSat, Oct 10, 2026 Β· 10am–5pm

City of Fairfax Fall Festival

City of Fairfax

More than 400 arts, crafts, information and gourmet food vendors, children's activities, and three stages of music and entertainment for all ages.

OCT24
FairfaxSat, Oct 24, 2026 Β· 10am–4pm

UCP Fall Art and Craft Fair

Fairfax County

Browse handmade art and original works from talented local artists β€” jewelry, pottery, seasonal dΓ©cor and more, supporting the community's creativity.

SEP19–20
FairfaxSat–Sun, Sep 19–20, 2026 Β· 12–5pm

Capital One Center Celebration of the Arts

Capital One Center, Tysons

An immersive two-day festival transforming the streets of Capital One Center into a multi-block celebration of the arts β€” interactive installations, hands-on workshops, live music and culinary experiences for every generation.

SEP4
FairfaxStarts Fri, Sep 4, 2026

Bluey x CAMP: Bluey's House

Tysons Corner Center (at CAMP)

Step inside the home of Bluey at this immersive pop-up experience for the littlest fans. Ticketed.

SEP4–6
FairfaxFri–Sun, Sep 4–6, 2026 Β· 7:30pm

Theatre in the Park: Woody Guthrie's American Song

Reston, VA

A musical journey through the songs and spirit of Woody Guthrie, staged outdoors in the park.

SEP11–12
LoudounFri–Sat, Sep 11–12, 2026 Β· Fri 5–8pm Β· Sat 12–8pm

Ashburn Village Fall Fest

Ashburn Village Sports Pavilion

Free community fall festival with live music, food trucks, kids’ activities and a beer garden. Optional activity wristbands cover bounce houses, petting zoo, pony rides and a video game truck.

SEP12
ClarkeSat, Sep 12, 2026 Β· 8am

The Big Flea β€” Fall 2026

23 E Main St, Berryville

A big seasonal flea market and antique sale in downtown Berryville β€” seek, discover, and explore.

OCT3
LoudounSat, Oct 3, 2026 Β· 12pm

38th Annual Leesburg Car Show

25 W Market St, Leesburg

Downtown Leesburg fills with classic and custom cars for one of the region's longest-running car shows.

NOV7–8
FairfaxSat–Sun, Nov 7–8, 2026 Β· 11am–6pm

Pickle & Grilled Cheese Festival

Bunnyman Brewing, Chantilly

A quirky food festival built around two beloved comfort foods β€” pickles and grilled cheese β€” with vendors, music and family activities.

SEP6
LoudounSun, Sep 6, 2026 Β· 12pm

LoCo Fest 2026

14001 Harpers Ferry Rd, Hillsboro

A big community festival celebrating all things Loudoun County β€” local vendors, food and live entertainment.

OCT11
LoudounSun, Oct 11, 2026 Β· 1pm

DTFest 2026

One Loudoun Carnival

A carnival takeover of One Loudoun β€” rides, games and family fun for the whole neighborhood.

SEP12
LoudounSat, Sep 12, 2026 Β· 11am

Oktoberfest Market at Bear Chase Brewing Co.

Bear Chase Brewing Company, Bluemont

A German-style market day at the brewery β€” vendors, food and family-friendly Oktoberfest fun.

SEP12–13
LoudounSat–Sun, Sep 12–13, 2026 Β· 11am–5pm

Fabbioli's Diagon Alley Market 2026

Fabbioli Cellars

A Harry Potter-themed vendor market at the winery β€” wizarding wares, crafts and family-friendly fun.

SEP26
LoudounSat, Sep 26, 2026 Β· 11am–4pm

Leesburg Airshow

Leesburg Municipal Airport

Hosted by Leesburg's Parks and Recreation β€” a full afternoon of aerial performances and ground displays for the whole family.

NOV14–15
LoudounSat–Sun, Nov 14–15, 2026

2026 DMV Chocolate and Coffee Festival

Dulles Town Center

A weekend celebration of chocolate and coffee makers from across the region β€” sampling, vendors and family-friendly treats.

SEP30
LoudounWed–Sat, Sep 30–Oct 3, 2026

47th Annual Mid Atlantic Police Motorcycle Rodeo

Dulles Town Center

Police motorcycle skills competitions and demonstrations from agencies across the region β€” a fun, family-friendly spectator event.

SEP24
LoudounThu, Sep 24, 2026 Β· 8pm

Movie Nights: Paddington in Peru

One Loudoun Park

A free outdoor movie night on the lawn at One Loudoun β€” bring a blanket and settle in.

OCT10
πŸ“ Beyond (WV)Sat, Oct 10, 2026 Β· 10am

Middleway Day β€” Village Street Festival

112 East Street, Middleway, WV

Celebrating the village's 250th anniversary β€” a street festival with local vendors, food and community history in one of the region's oldest villages.

πŸƒ Lace Up

Fall Runs & Races(8)

β–Ά Click to expand
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5Ks, fun runs, and races that double as a good excuse to be outside while the weather's perfect.

NOV21
LoudounSat, Nov 21, 2026

Freeze Your Gizzard Cross Country 5K & Fun Run

Ida Lee Park, Leesburg

A 5K and 1-mile fun run benefiting Loudoun Hunger Relief β€” a Leesburg late-fall tradition.

SEP5
FauquierSat, Sept 5, 2026 Β· 7:30am

Dog Days of Summer 5K & 10K

Warrenton Aquatic & Recreation Facility, Warrenton

A dog-friendly 5K/10K on the rolling hills and trails around WARF, benefiting the Lost Dog & Cat Rescue Foundation. Strollers and walkers welcome.

SEP6
FauquierSun, Sept 6, 2026 (confirm time)

Running on Lemonade 5K

Warrenton, VA

A community 5K and 1-mile run in Warrenton supporting children and families battling cancer.

SEP12
FairfaxSat, Sep 12, 2026 Β· 7am

2026 Pleasant Valley 5K Run/Walk & Aquathlon

Pleasant Valley Recreation Area, Chantilly

A 5K run/walk, a swim/run aquathlon, a virtual 5K option, and an afternoon dog swim β€” proceeds support the Pleasant Valley Pool and two local charity partners.

SEP26
πŸ“ Beyond (MD)Sat, Sep 26, 2026

Run On The Rocks β€” 10 Miler, Half Marathon & 20 Miler

Point of Rocks Boat Ramp, Point of Rocks, MD

A flat, scenic out-and-back on the C&O Canal Towpath along the Potomac β€” just across the river from Loudoun. Chip-timed, custom finisher medals.

SEP19
πŸ“ Beyond (MD)Sat, Sep 19, 2026 Β· 8am

Muddy Mamas Mud Run + Obstacle Course

Washington County Agricultural Education Center, Hagerstown, MD

A big, family-friendly mud run and obstacle course β€” 971 people already marked interested. A different kind of fall outing.

SEP13
LoudounSun, Sep 13, 2026 Β· 9am

Heeling House 5K

Ida Lee Park, Leesburg

A charity 5K supporting a local dog rescue organization β€” a family-friendly run through Ida Lee Park.

OCT25
LoudounSun, Oct 25, 2026 Β· 8am

Second Annual Waterford Bicycle Classic

Wheatland Spring Farm + Brewery, Waterford

A scenic ride through Loudoun's historic countryside, starting and ending at the brewery β€” multiple route lengths for all riding levels.

🍁 Blue Ridge & Piedmont

Foliage & Outdoors(13)

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Farm tours, orchards and drives to catch peak color in the Blue Ridge foothills.

OCT10
FauquierSat, Oct 10, 2026 Β· 10am–4pm

Fauquier Fall Farm Tour

Fauquier County

Self-guided tour of local farms β€” field crops, livestock, hayrides, pumpkin patches, petting zoos and farm-fresh flavors across the county.

FALL2026
LoudounWeekends through fall 2026

Bluemont Vineyard & the Blue Ridge foothills

Bluemont, VA

Right across from Great Country Farms β€” sweeping mountain-view foliage with a glass of wine, easily paired with a farm visit the same day.

SEP13
LoudounSun, Sep 13 Β· Sun, Oct 4 Β· Sun, Oct 18, 2026

VHSA Hunter Show Series

Red Gate Farm, Bluemont

Family-friendly spectator horse shows at a welcoming, family-oriented equestrian center β€” great footing, spectator seating, and a fun atmosphere for all riding levels.

SEP20
LoudounSun, Sep 20, 2026 Β· 8am

Fall Starter Horse Trial and Combined Test

Red Gate Farm, Bluemont

An eventing competition open to spectators β€” cross country, dressage and jumping in one family-friendly outing.

OCT11
LoudounSun, Oct 11, 2026 Β· 9am

VHSA/BHSA/TIP Jumper Show

Red Gate Farm, Bluemont

A regular jumper show that happens to land near Halloween β€” not holiday-themed, just a great weekend for horse-loving families to watch some jumping.

OCT26
LoudounMon, Oct 26, 2026 Β· 7–8pm

Full Moon Hike β€” Hunter's Moon

Franklin Regional Park, Purcellville

An evening guided hike timed to October's Hunter's Moon, hosted by Loudoun County Parks, Recreation and Community Services.

NOV14
LoudounSat, Nov 14, 2026 Β· 8–10am

Reel Memories Trout Derby

Lovettsville Community Park

Anglers of all ages cast in for a whopper of a good time β€” prizes for the most fish caught in each age category. Under 16 must be accompanied by an adult.

SEP19
LoudounSat, Sep 19, 2026 Β· 5:30–7pm

Twilight Canoe Paddle

Franklin Park, Sleeter Lake

Paddle into the golden glow of evening and take advantage of twilight to watch birds return to their roost. Life jackets provided and required.

OCT8–11
LoudounThu–Sun, Oct 8–11, 2026

Morven Park International

41580 Sunday Morning Ln, Leesburg

A world-class equestrian driving competition set on Morven Park's historic grounds β€” a beautiful fall spectator event for the whole family.

OCT3
ClarkeSat, Oct 3, 2026 Β· 11am

First Saturdays at Sky Meadows

Sky Meadows State Park

A monthly state park program with hikes, history and hands-on nature activities for families.

SEP26
LoudounSat, Sep 26, 2026 Β· 10:30am

Hiking Meet-Up at Dirt Farm

Dirt Farm Brewing, Bluemont

A community hiking meet-up starting at the farm, exploring the surrounding Blue Ridge foothills.

SEP26
πŸ“ Beyond (MD)Sat, Sep 26, 2026 Β· 1pm

7th Annual Polo Classic

14660 Hughes Rd, Poolesville, MD

An afternoon of polo matches, tailgating and family fun at a picturesque farm setting β€” presented by MARS.

SEP12
πŸ“ Beyond (MD)Sat, Sep 12, 2026 Β· 5pm

Wildlife and Waves: Evening Kayaking Tour

Brunswick Family Campground, MD

A guided evening kayak tour along the Potomac β€” watch for wildlife as the light turns golden over the water.

🎢 An Evening Out

Concerts(1)

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Ticketed concerts and shows worth the drive this fall.

SEP4
FairfaxFri, Sept 4, 2026 Β· 8pm

Jerry Garcia Symphonic Celebration ft. National Symphony Orchestra

Wolf Trap, Vienna

The National Symphony Orchestra performs a symphonic tribute to Jerry Garcia at Wolf Trap's outdoor Filene Center. Tickets required.

πŸ¦ƒ Looking Ahead

Turkey Trots & Thanksgiving Preview(2)

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A quick preview of what's coming in Thanksgiving week β€” the full guide (parades, food drives and more) lands at thanksgiving.joyinnova.com when it's ready.

NOV14
ClarkeSat, Nov 14, 2026 Β· 5K 9am, Kids Fun Run 10am

Berryville Turkey Trot 5K & 1 Mile Kids Fun Run

Chet Hobert Park, Berryville

Celebrating 5 years β€” a chip-timed 5K and kids fun run hosted by John H. Enders Fire Company & Rescue Squad, with top-3 age-group awards and a food drive for FISH of Clarke County.

NOV21
FauquierSat, Nov 21, 2026

Gobble Gobble Run or Wobble

Warrenton, VA

A community Thanksgiving-week fun run/walk in Old Town Warrenton β€” open to all paces.

Also on the way for Thanksgiving week: the Lansdowne, Herndon, Purcellville and Reston turkey trots β€” 2026 dates aren't confirmed yet, so check back or watch thanksgiving.joyinnova.com once it's live.

πŸ—“οΈ
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🍁 Fall Resources

Plan your leaf-peeping around the week

Official Report

Virginia Fall Foliage Report

The Commonwealth's own tracker for when and where color peaks each year β€” generally October 10–31, earliest at higher elevations.

virginia.org β†’
Daily Foliage Map

ExploreFall.com β€” Virginia Map

Daily-updated, data-driven fall color map with a 10-day forecast. Built in part by Peter Forister, a Virginia Tech geography grad and a friend of ours.

explorefall.com β†’
Photography

Fall Photos by Peter Forister

Gorgeous fall galleries from around Virginia and the Blue Ridge, shot by the same Peter behind ExploreFall's maps.

peterforisterphoto.com β†’
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