It may not quite feel like it today, but fall is just around the corner in Loudoun County. And though I could be biased, I’d argue that Loudoun is one of the best places to find yourself as the leaves begin to change and there’s a touch of chill in the air. Looking for things to do in Loudoun in fall 2022? Check out a few local options with that Loudoun flair you don’t want to miss.
For the ones who have been ready for fall since June…
Yes, we get it. Sometimes fall is more than just a season, it’s a whole mood. Sweaters, warm drinks, not sweating the moment you walk out the door, all those ‘just autumn things’. If you’re nodding your head, these activities are what you’re looking for.
Great Country Farms
If you’ve spent any time in western Loudoun, you’ve likely either visited or heard of Great Country Farms. At this time of year, they have all the IG-worthy fall festivities that come to mind when you think of things to do with your pumpkin spice latte. You could:
- Sep 1-30: Sip apple cider while getting lost in a corn maze
- Oct 1-31: Find your perfect pumpkin (protip: go buy your tickets now. Seriously. They do sell out and if you’re reading this and still in shorts, now is the time.)
- Dates TBD, but was in November in 2021: Try your hand at “Pumpkin Chunkin’”
There are plenty of other fall activities sprinkled throughout the season. So make sure to stop by their website for the latest. And don’t forget your flannel.
The Bluemont Fair
September 17-18
Another autumn staple in the Loudoun landscape is The Bluemont Fair. This annual event is a fantastic opportunity to explore the 200-year old village of Bluemont while perusing local crafts and seminars. Oh, and of course, there’s plenty of local wine to be found as well.
Wondering what to expect? Check out the following:
For the ones who always do their holiday shopping early…
We all have that one friend who somehow manages to get their gift shopping done before any of us have even started to make a list. Maybe you can invite them to one of these events and get your shopping done too?
Vanish Sip and Shop
September 18
Hosted at Vanish Farmwoods Brewery, this event features plenty of local artisans with a wide range of products for sale. You can also probably find your new favorite beer from Vanish’s expansive selection.
Some of the vendors you can expect at Vanish include:
- Little Clay Daisy
- Second Life Decoupage
- DeeDee’s Jams
- Chappelle Candle Company
- LoZo Spice Blends
The list above is just a taste of what you can enjoy. Check out the full list and get further details on their event Facebook page. And speaking of tastes, Nomini Bay Oysters will also be there all day, serving up freshly shucked oysters. (prefer something cooked? Burger and taco food trucks will also be onsite)
The Waterford Fair
October 7-9
Landmark artisans? Check. Living historians? Check. Historic home tours? You got it. And local libations to tie it all together? You guessed it. As the name suggests, The Waterford Fair is located in the National Historic Landmark of Waterford, which is just about as quintessentially Virginia as you might imagine.
If you’ve never seen a demonstration by a landmark artisan, you can’t really appreciate the level of detail and expertise that goes into their work. To reach this status they must use traditional methods and be approved to participate. You can learn more about the landmark artisans that will be in attendance here.
Proceeds go to supporting historic preservation efforts in the village.
LoCo Latino Festival
October 23
This community festival in Leesburg celebrates and showcases Latino culture. Featuring a wide range of foods, crafts, and activities, this is a great one to bring the kids too as well. As for the shopping? You can find plenty of local and regional businesses, non-profits, and commercial vendors. ¡Nos vamos!
Get more details here and here.
For the ones who have the best Spotify playlists…
You know, the ones who always take on DJ duties on road trips or at parties. In any case, they are in luck if they’re a Loudoun local as there’s no shortage of musical happenings around town. Check out just a few of them below.
LoCo Fest 2022
September 4
Get your dancing shoes on for the 5th annual LoCo Fest, featuring 25+ Loudoun County musicians. Hosted at 868 Vineyards in Hillsboro, there will be plenty of food, beer, and wine to keep you going. Prefer a more chilled approach? Bring your own chairs, blankets, and even pop up tents!
Another cool part about this event is that it’s a fundraiser to support up-and-coming artists in Loudoun. To date, it has generated over $20,000 in music equipment for local musicians.
In other words, if you don’t have plans on the 4th, find some friends and get your tickets for the event here. (Tickets will also be available at the door)
Crossroads Music Festival
September 17
Crossroads Music Festival takes place in downtown Leesburg and is a showcase of musicians local to the greater DMV region. This all day event features several different stages dotted throughout downtown – so there’s never a lack of variety in your music choices.
Put on by Benefit, proceeds from this event go on to support local charities serving children. So, not only do you get to hang out and listen to great music in Leesburg, you can feel extra good knowing that your ticket is contributing to a fantastic cause.
Here’s the schedule:
Ready to rock? You can buy your tickets or see more details about the event.
HOUSE in the Country at Lost Barrel Brewing
September 24
Looking for a slightly different vibe? Head on out to Lost Barrel in Middleburg for a sundown session with DJ Heather Femia and DJ Matt Dillon. They’ll be playing some house classics in the beautiful backdrop of horse country.
And of course, there will be plenty of space to dance – so come ready to be transported to an oceanside club, without ever getting on a plane. After all, who needs Ibiza when you’ve got Middleburg?
Get the details on the event’s Facebook page.
For the ones who wait patiently but are secretly only there for the food…
Every friend group has one. That person who always manages to pick the most delicious things on the menu. AKA: the foodie. But deep down, aren’t we ALL foodies? 😉
Dining in the Dark
October 13
Held in support of Loudoun Therapeutic Riding, this five-course meal will be served in low light and with eyeshades so that diners can have a full immersive experience. Your chef for the evening, Christine Ha, is blind, and won “MasterChef” season 3 with Gordon Ramsay.
Hosted at Bourbon Bayou Kitchen in Ashburn, this event will be truly unforgettable. Not only because of the experience itself, but also because of the positive impact that your support can have.
See more details about the event or buy your ticket today.
OysterFest & Rescue Ale IPA Release Day
October 15
An entire festival for oysters AND rescue dogs? Sign me up.
Bring your dog and your appetite because Arielle Oyster Company will be serving raw oysters, grilled oysters, peel and eat shrimp, bacon-wrapped scallops, and much more. The event itself is free but they are requesting that people RSVP so they can plan how many delicious shelled delights to bring.
It’ll also be release day for their Rescue Ale IPA. Aside from being a very tasty beer, a portion of the proceeds will go to supporting local animal rescues.
Loudoun Veg Fest
October 30
If eco-friendly vegan cuisine is your jam, this is the event of the season. And if you’re omnivorous but veg-curious, it’s for you too. There will be speakers, live music, and of course, a wide range of vegan foods to try.
Loudoun Veg Fest is free to attend, so it’s a great way to capture those last bits of Loudoun County autumn weather. So, be sure to come with an empty stomach and your reusable grocery bag to carry your vegan haul home.
For the family that wants to experience something different that Loudoun has to offer…
Loudoun is more than just pumpkin festivals, wineries, and delicious foods – though there’s certainly nothing wrong with enjoying these. Got a group that includes the whole family? These events are perfect for groups of all ages.
Luau at Ohana
September 10
Who doesn’t like hula dancers and Hawaiian feasts?
Extra points if you can drive to Aldie instead of the airport to experience it.
Hosted by the Ohana Preservation Foundation, this event features more than just a Hawaiian flair. Instead, you can dress the whole family up in your most festive Hawaiian attire for your chance to win a prize. There will also be a mechanical surf ride, animals, a bounce house, and of course, a wine and beer tap truck for the parents. Something else you’re unlikely to find in Loudoun? Tomahawk-throwing. So yes, there really is something for everyone at this event.
This event will be held rain or shine and all proceeds will support Ohana Preservation Foundation’s mission, in addition to the 2022 charity beneficiary, Capital Caring Kids, a local children’s hospice and bereavement organization.
Get your tickets or learn more today.
Creepy Creatures and Animals in Fall and Winter Puppetshows
September 17
One of my favorite things about living in Loudoun is the wide range of wildlife that is local to the region. And if you’ve got some little ones in the family, the changing of the seasons is the perfect time to get to know the first “locals” of the region.
Held at Claude Moore Park, this is a great way to spend a little time outside – and you might even learn something new too! There will also be tons of fun things to see and do including live music, great food, and plenty of nature related activities.
See all the details here.
SterlingFest
October 8
This annual event is the biggest block party of the year. It takes over multiple streets adjacent to the Sterling Community Center, creating the ideal space to get to know your neighbors and the community at large.
It includes booths with offerings from a wide range of local vendors, LOTS of different food choices, and a beer garden for the adults in the group. There will also be plenty of games, obstacle courses, and even crafts for the kiddos to enjoy.
SterlingFest is free to attend, but be sure to bring some spending money! A portion of the proceeds will go to The Sterling Foundation, which aims to strengthen and beautify the town.
For the ones who are ready to experience the best wines Loudoun has to offer…
Sometimes known as the Napa of the east coast, Northern Virginia, and Loudoun in particular has some truly spectacular wines. So, of course, it’s crucial that we take advantage of the gorgeous fall weather to enjoy them.
Boxwood’s 2022 Harvest Tour
September 24
Ever wondered what it takes to execute a fall wine harvest at a working vineyard? Head on out to Middleburg during their annual fall tour to get a behind-the-scenes look at the harvesting process.
You’ll get the chance to tour the winery facilities with the vineyard manager and get an insider look at the fruit selection, fermentation, and aging processes. And what winery tour would be complete without a taste of the finished product? Your tour includes a half bottle of select wine.
Get your tickets here.
Virginia Wine Festival
October 1-2
A festival dedicated to wine held at One Loudoun? Sounds good to me. Your general admission ticket includes a tasting glass, unlimited tastings from a number of VA wineries, and access to the VA Oyster Pavillion. There will also be a wide range of concessions and musicial entertainment available to keep you busy all day long.
And if walking around tasting wine builds up an appetite, fear not, as there will be no lack of food trucks available for you to choose from.
This event tends to sell out, so buy your tickets here. Need more info? Check out the event’s website.
2022 Loudoun Wine Awards
October 14
It would make sense that in an area so rich with quality vineyards, we’d need an entire awards program dedicated to wine.
Now entering its 7th year, the Loudoun Wine Awards aim to highlight the best wines that Loudoun vineyards have to offer. There will be a tasting of the award winning wines, followed by an awards reception and dinner (you can see the menu in the link below).
Want to attend? Reservations are required, and you must be 21 to enter. There will also be a raffle benefiting Harvest Kindness, an organization providing grants throughout the local agricultural community.
For anyone who didn’t realize how many Oktoberfests Loudoun has…
Ah yes, Oktoberfest. You’re likely thinking of Germany, beer, and sausages. But you don’t have to dust off your passport to get into the Oktoberfest mood. Instead, check out some of the local Oktoberfests you can add to your calendar in Loudoun this year.
Oktoberfest @ Bear Chase Brewing Company
September 10
Get a jump on the festivities at Bear Chase. This popular event will feature live music, German outfits, and of course, plenty of beer.
Visit their Facebook event for more details.
Bonus event: Bear Chase holds an additional Oktoberfest / Beer fest on October 22. Learn more here.
Middleburg Oktoberfest
September 17
Held in downtown Middleburg, you can expect to enjoy two biergartens, traditional German eats, live music and even an art fair. There will, of course, be beer available for sale from local vendors.
See details and photos from last year here.
Lovettsville Oktoberfest
September 23-24
The German village of Lovettsville is known for putting on quite the Oktoberfest. There will be a number of events throughout the weekend, not to mention local vendors for food, beer, and beyond.
See what you can expect here and get your tickets here.
Oktoberfest @ Dirt Farm
September 24
Ready for seasonal beer and German-inspired food choices? Stop by Dirt Farm for their annual Oktoberfest. There will also be live music, axe-throwing, and some fun Oktoberfest swag.
See more here.
Oktoberfest @ Village at Leesburg
October 2
Conveniently located just minutes from downtown Leesburg, this Oktoberfest will help you to ring in the new month with beer, brats, and German attire.
Learn more here (no tickets required).
For the ones who have the BEST costumes this year (and have had it ready since August)…
Spooky season is nearly upon us. An excuse to eat a pound of candy, the time to break out your best DIY tailor skills, or the perfect day to curl up with Michael Myers and Jason Voorhees. Whatever it means to you, you’ll find no lack of ways to celebrate in Loudoun.
4th Annual Halloween Bark Bash
October 29
Some of my best Halloween memories include a furry friend. And this year if you’re in the neighborhood with Fido in tow, stop by One Loudoun for this annual event.
Held outdoors, the Halloween Bark Bash is a Halloween-themed festival featuring local animal rescues, pet-focused businesses, and of course, pets and their owners. There will be trick or treating, music, costumes, and of course, adoptable dogs.
All Ages Read Together (AART) 10th Annual Halloween Hoedown Fundraiser
October 29
What’s fall without a Halloween Hoedown? This one features a BBQ buffet (including vegetarian options), a live band, a silent auction, and of course, a costume contest. This is a great option for families with kids of all ages; there will be arts & crafts, an inflatable bouncehouse, and games.
This is also a hoedown you can feel good about because proceeds will help to support AART’s mission to provide free preschool classes to children who need them.
Get more details and your tickets here.
Halloween Tea
October 30
A traditional English afternoon tea meets Halloween.
Head on out to Oatlands Historic House and Gardens to enjoy English scones, Devon cream, tea sandwiches, and of course, all the tea you can drink. What makes it part of spooky season aside from the date? Treats will be Halloween themed.
Tea is served at three different times throughout the day (10:30am, 12:30pm, and 2:30pm), so get your tickets and choose your slot here.
For the ones who are up for anything (as long as they don’t have to plan it)…
Yep, there are plenty of miscellaneous activities that don’t really fall into any of the categories above, but are still absolutely worth stopping by. These require minimal planning and in most cases, don’t need to be pre-registered for (though be sure to check the links so that you’re not surprised).
Loudoun Pet Expo
September 11
Launched in 2014, this annual event promotes community support and awareness for local pet businesses, non profits, and rescues. It’s a family friendly event, where of course, pets are welcome. There will be vendors, educational sessions, and plenty of new furry friends to meet.
Learn more about the event here.
Leesburg Airshow
September 24
With a wide range of aircraft and performers, as well as attractions on the tarmac, this event promises to be a fabulous day of high flying fun. Aerial performances begin at 1pm, but doors open at 11am for anyone who wants to look at these incredible feats of engineering close up.
There will also be a range of local food vendors available. And beer. Because is there really a better combination of activities than watching airplanes, drinking beer, and enjoying those first few days of fall weather?
Get directions and see what you can expect here.
Bob Ross Painting Workshop
October 15
It’s always a good time to paint a happy little tree.
In this upcoming workshop, you’ll complete a 16×20 original painting, with step-by-step instructions from a certified Bob Ross instructor to help you get there. All materials are included in your fee and the painting will take about 3 hours to complete.
Lost Barrel Brewing Cars & Coffee
October 29
Is there a better combination of activities than caffeine and horsepower? Probably not, but I’ll let you know if I find one. This recurring event happens on the last Saturday of each month from 9-11am. Bring your car, motorcycle, or other engine-having contraption and enjoy some delicious coffee and company from other gearheads.
Check it out here.
Fall activities in Loudoun County: which is your favorite?
These are just a few of the fun things you can do to pass the autumn season in Loudoun. Are there any I’ve missed that should be included here? Leave me a comment!
And of course, if you stumbled across this post and are looking for a new home in Loudoun, contact me directly to get a complimentary list of homes for sale that meet your criteria. You can reach me at sian@sianpugh.com.
Leave a Reply