October is finally here, and it’s welcoming us with the gorgeous mild weather we’ve been waiting for! This holiday weekend, it’s all about the fairs and festivals. Whether you bring the whole family or fly solo and make festival friends, you’re going to have a great time with this impressive lineup. So, who’s the fairest of them all? 


The Arts & The Crafts  

Come on out for a 3-day celebration of all things handmade at the Waterford Fair! Explore more than 100 artisans from across the country, all gathered in the National Historic Landmark of Waterford, Virginia to exhibit and demonstrate jewelry, clothing, furniture, metal and home decor crafts. Don’t miss this chance to touch, feel and explore high-quality American crafts and meet the makers behind the fabulous work. Get a headstart on holiday gifts (it’s never too early, right?) when you browse through the Fine Art Exhibit and Art Mart Sale, the Old Mill Shop, the Dried Flower Barn and the Photography Show. Enjoy stellar entertainment on the main stage while reenactors and entertainers stroll throughout the village!

If you’re like us, you’re always in the mood to sway along to some sweet, sweet jazz. Swing by Tracy Hamlin's inaugural Sweet Jazz Festival, as international saxophonist Gerald Albright, pianist Alex Bugnon, vocalist Tracy Hamlin, trumpeter Cindy Bradley and other Loudoun County jazz artists take the stage at Shadow Lake. While you’re there, enjoy food truck treats, luxuriate in the crisp autumn evening and celebrate Virginia Wine Month by savoring a few sips of delicious wine from Tarara Winery. As if we weren’t already super jazzed for the weekend!

Display your support of the arts by attending the opening weekend of The Byrne Gallery’s “Coalesce” exhibit! Artists Christine Olmstead and Marta Staudinger bring synergy in mind and spirit to this exhibition of their expressive abstract paintings. With a consistent color palette, the two artists sought to emphasize the importance of color in expressing mood and perspective, as we all instinctively select certain colors of various hues and tones to populate our lives. The special tranquility that this thoughtfully created exposition evokes will lift and inspire each viewer to enjoy and relish the beauty surrounding us daily.



Celebrate the season — autumn, that is — at this weekend’s lineup of fall festivals! First stop, the 25th Annual Fall Pumpkin Harvest Festival at Great Country Farms, where you can enjoy everything fall as you help celebrate the last harvest of the season and October’s top crop! 🎃 Bump along on a wagon ride out to the patch to choose your very own great pumpkin. Comb through the corn maze for 1.5 acres of a-maize-ing fun, followed by lots of laughs in the 5-acre play area! Don’t miss the heart-racing Triple Threat 80-foot slide, the 2,800 square-foot Pumpkin Jumpin’ Pillow, the pedal cart track, rope swings and the Cow Pie Putt-Putt Course. Then, it’s bombs away at the pumpkin cannons; aim true for those field targets! After a visit with the barn animals, shop the Farm Market for seasonal fresh produce, jams & jellies, honey, local meats, baked goods and great gift ideas from local artists. Stock up on seasonal fall favorites like fresh cider, 100% natural cider slushies, corn stalks, gourds and apples! Get your festival feast on at the Roosteraunt Concession Stand, featuring hand-dipped pumpkin ice cream, pecan wood-smoked pork BBQ sandwiches with classic coleslaw, kettle corn, freshly baked apple pies and everyone’s favorite: cider donuts. Keep the sweets coming with roasted marshmallows by the bonfire. Big fans of smashing pumpkins will find a friend in P-Rex the Pumpkin Munching Dinosaur, who roars into action for the P-Rex Pokey, a little dino flossing and a lot of pumpkin chomping (look out, he’s a messy eater). 🦖

Gather together and give thanks for the year’s bountiful harvest at Willowcroft Farm VineyardsHarvest Celebration! Please your palate with your pick of five award-winning Willowcroft wines paired with five “fall” comfort foods. This harvest celebration stems from a rich history of Loudoun agriculture, as it was the Willowcroft team who first brought wine to what is now DC’s Wine Country! After planting the first grapes in 1981 on the slopes of a nineteenth-century orchard, Willowcroft opened in 1984 with vintages from their first fruits. Taste the tradition in Willowcroft’s large rustic red barn that dates back to the Civil War, and enjoy the view of autumnal foliage from the picnic tables perched high atop Catoctin Ridge. Soak up the peaceful panoramic views of Loudoun Valley and the Blue Ridge Mountains as you drink in the flavors of fall’s harvest!

We’ll just leave you with one final spook: Shocktober opens this weekend! While we’ve already mentioned Shocktober, these delightful frights are worth a reminder. If you feel brave enough to face the horrors around every corner of Paxton Manor, make your way to Northern Virginia’s only REAL Haunted House and the best destination for Halloween entertainment in Leesburg, Virginia and the DC area. Creep through the 32 rooms and basement of terror, then qualm your fears with the Loudoun County beers and wine on sale. Don’t forget that they scare because they care: all proceeds from Shocktober benefit The Arc of Loudoun, a full-service nonprofit that serves children with disabilities and their families!





First Friday with the Crooked Angels & Market Salamander - October 5 at Greenhill Winery & Vineyards

The Ultimate Michael Jackson tribute: Who's Bad - October 5 at Tally Ho Theater

A Progressive Tasting Experience - daily at 50 West Vineyards and Sunset Hills Vineyard

Barktoberfest: A Purrfect Pet Celebration - October 6 at Loudoun County Fairgrounds

Brambleton Fall Fest - October 6 at Brambleton Town Center

Fall Festival by Joshua’s Hands - October 6 at Guthrie Farm

Loudoun Symphony Presents New Horizons - October 6 by Loudoun Symphony Orchestra

Mewsic and Brews - October 6 at Old Ox Brewery

The Michael Allman Band - October 6 at Tally Ho Theater

Decanting Class at Breaux Vineyards - October 7 at Breaux Vineyards

Vineyasa Yoga & Wine - October 7 at Greenhill Winery & Vineyards