Halloween is nearly upon us, and you know what that means: Jack-O-Lanterns! What would October be without a little pumpkin carving, right?! After trick-or-treating in downtown Leesburg on Saturday, Shoe’s Cup & Cork invites everyone to stop by for some crazy carving! Do your Halloween duty and decorate your doorstep with these gruesome gourds 🎃 Then, dive headfirst into your Halloween sugar rush in the pie eating contest! Crust Trust us, just one taste of the baked goods served up at Shoe’s Cup & Cork will leave you filling feeling ready for another bite… and another, and another 🥧 We’ll see you at the Pumpkin Carving and Pie Eating Contest — in costume, we hope!

Recent studies have indisputably proven that about 70% of the fun of being a dog owner derives from dressing them up in adorable Halloween costumes. Dachshunds in hotdog costumes? Yes, please. Shih Tzus dressed as Ewoks? Bring it on. Dalmatians in little firefighter outfits? We are 100% here for it. And it’s every dog for himself in the 868 Estate Howl-o-ween Dog Costume Contest! Doll up your furry friends and roll out the leashes for an afternoon of vino, crisp fall air and friendly competition (with wine-related prizes, of course). Is your dog the Scariest? Silliest?  Crowd favorite? Or are the two of you the “Best Twinned”? We’re jumping and spinning with Howl-o-ween excitement!

Just one final question begs to be asked: “You want a trick treat?” 🐶

If there’s one thing you can count on, come Halloween, it’s candy. There’s no exception here in Loudoun County, although we like to incorporate wine at every opportunity 😉 Thus, Halloween Candy and Wine Pairings! Make your way to Fabbioli for the cellar’s annual Halloween event, at which guests are treated to delicious vino, accompanied by everyone’s favorite candies. Sounds like a devilishly good time, to us. How else would you expect us to pregame Halloween in DC’s Wine Country?!

Ready for one final fall festival?! Ford’s Fish Shack saved the best for last with an activity-packed Oktoberfest that sounds like a blast! Bring the whole family to Dulles Golf Center & Sports Park for a fun afternoon of unlimited access to the golf driving range, batting cages, miniature golf course, basketball and volleyball courts. All you cornhole kings and queens out there, bring your A-game to the Corn Hole Tournament, in which the winning team will receive both a $75 Ford’s Fish Shack gift card and a round of mini golf for four at Dulles Golf.


Here’s a sneak peek of what German fare the buffet will feature: a German seafood boil with brats, cod and shrimp; traditional Oktoberfest sides, like German potato salad, pretzels, braised cabbage and roasted Brussels sprouts; and a delectable dessert of white chocolate blueberry bread pudding. (Don’t worry, there will also be burgers, hot dogs and mac & cheese for your favorite picky eater!) Of course, it wouldn’t be a true Oktoberfest without lots of local seasonal beer! Fill up your stein one last time with seasonal craft beers by Old Ox Brewery, Lost Rhino Brewing Company, and Solace Brewing Company. We’ll prost to that!



Frightening Fun after Nightfall

Halloween isn’t all scary! If you feel full of fright, laugh it off at a Halloween Stand-Up Comedy Show! The professional comedians and incredible wine at Winery 32 will placate even your worst fears. Headliner, Mark Matusof, will keep you laughing all night long with scary-good fun! You’re welcome, Hallo-winos 😂🍷

After a good spook, we find that the best scareapy therapy is to just dance it out. Break out your favorite mask and most killer dance moves for a Halloween Risqué Masquerade at B Chord Brewing! Make the Boogie Man proud as you boogie down on the dance floor and let your freak flag fly 💃🕺






A Night at the Oxbury - Oct. 26 at Old Ox Brewery

On Fly in the Salt: Talk & Tour - Oct. 26 at National Sporting Library & Museum

October Paint and Sip - Oct. 26 at Breaux Vineyards

Temple Hall Farm Fall Festival & Corn Maze - daily at Temple Hall Farm Regional Park

Pumpkin Village and Fall Festival - daily at Leesburg Animal Park

Fall Pumpkin Harvest Festival - daily at Great Country Farms

Shocktober Haunted House - Oct. 26, 27, 28 at Paxton Manor