Loudoun is glorious in the fall. The air is crisp and cool, early morning mist hangs in the valleys and the lush green of farm fields is offset by explosions of burnt yellow and salmon red from forests of oak, ash and maple. It’s also a great time to get out and celebrate the harvest.
Here are our top five things to do in Loudoun this fall.
Celebrate the Grape
October is Virginia Wine Month, which coincides with the annual Loudoun Wine Awards. The flagship event of the Loudoun wine calendar showcasing the best wines in the county will be held on Friday, October 24 at Lansdowne Resort. Fall is also a great time to visit the wineries and celebrate the harvest. Aside from the usual tastings, several wineries offer special fall events. The third Loco Wine Festival featuring more than a dozen local wineries as well as live music and food trucks takes place at Old Farm Winery at Hartland on September 27 and 28. Out west, Breaux Vineyards’ annual Harvest Festival takes place October 25-26: great food, tastings, live music and stunning views of the Fall foliage.
Visit a Farm
Great Country Farms offers apple and pumpkin picking through September and October on a ticketed basis. Kids can get lost in a corn maze and then feast on apple cider donuts. Temple Hall Farm near Lucketts is open daily for pumpkin picking throughout October while Wegmeyer Farms caters to people looking to find that perfect carving pumpkin. Get decorating!
Fairs and Festivals
The 81st Waterford Fair takes place the first weekend of October (3-5) with its traditional craft displays, magic acts, music, art, artisans and behind-the-curtains tours of historic homes. The annual Loudoun Fall Farm Tour takes place October 18-19 with dozens of small, family-owned farms opening their gates and fields to the public. The Middleburg Film Festival runs from October 16-19 drawing in big name stars and Oscar-buzz worthy movies. Fall is also Oktoberfest season and there are several special events in Loudoun. A few to check out include the 5th annual Middleburg Oktoberfest on September 20 with two biergartens, traditional German food, work from local and regional artists, live music and more; the following weekend, the celebrated Lovettsville Oktoberfest returns with lederhosen, bratwurst and local craft beer. If you don’t want to wait that long, Wheatland Spring Farm + Brewery Oktoberfest is September 13-14. This year’s festival will also include German dance lessons by a local instructor and performances from renowned Hornist and Alphornist Shawn Hagen. A member of the National Chamber Winds, Hagen is a frequent guest of the Kennedy Center Opera House Orchestra, the National Symphony Orchestra, and the Baltimore Symphony Orchestra.

Into the Wild
Experience the full glory of fall at a cabin or on a camping trip in the Loudoun wilderness. In Sterling’s Algonkian Regional Park on the banks of the Potomac River, you can rent one of 12 winterized vacation cottages. Cottages have two to five rooms, full kitchens, deck and grill – perfect for gazing out on the red and gold canopy along the riverbank. In western Loudoun, Harpers Ferry Adventure Center on a hilltop in the Blue Ridge has rustic cabins and a full-service campsite in which to pitch your tent. There’s a zipline course and brewery on property too.
Leaf Peeping
Loudoun is blessed with multiple vantage points to see the leaves at their peak. Make your way to Bear’s Den above Bluemont for spectacular west-facing views of the Shenandoah Valley, the forest canopy a swirl of red, gold and purple below. Hike the “Rollercoaster” stretch of the Appalachian Trail from here toward Round Hill, the trees above you an umbrella of gold. Back on lower ground, hop on your bike and cycle the Hamilton to Purcellville stretch of the W&OD Trail. The leaves along the path have all turned, and you have stunning front-on views of the Blue Ridge in the distance. In eastern Loudoun, explore 11 miles of hiking trails through wooded lanes and by sparkling ponds.




