The Shenandoah Valley is beautiful any time of year, but there’s something especially memorable about visiting during Virginia’s wine and harvest seasons. From summer wine festivals to colorful fall celebrations, the region offers plenty of opportunities to sip, explore, and enjoy the best of Virginia wine country.
Glen Gordon Manor makes an ideal home base for your getaway. Relax in one of our luxurious rooms and suites, enjoy breakfast each morning, and spend your days exploring nearby vineyards, historic towns, and seasonal events.
Below are some of the annual wine and fall festivals to consider when planning your stay.
Shenandoah Valley Wine Festival
Annually, late June
What to Expect: Virginia wine, local food, live entertainment, and regional wineries.
Held at the Museum of the Shenandoah Valley in Winchester, the Shenandoah Valley Wine Festival brings together wineries and wine lovers for an afternoon of tastings and entertainment. It’s an easy way to sample wines from across the region while enjoying food, music, and the museum’s beautiful setting.
Shenandoah Sips at Belle Grove
Annually, late August
What to Expect: Virginia wines, ciders, spirits, live music, food trucks, and historic scenery.
Shenandoah Sips at Belle Grove celebrates Virginia-made beverages with wine, cider, spirits, live music, food trucks, chef demonstrations, vendors, and family-friendly activities. Set on the grounds of the historic plantation in Middletown, it’s a fun way to combine local history with the flavors of Virginia.
LoCo Fest
Annually, early September
What to Expect: Live music, a vineyard setting, food, and Virginia wine.
Hosted at 868 Estate Vineyards in Loudoun County, LoCo Fest brings together more than 25 musicians for an all-day celebration of local music. Guests can enjoy the vineyard setting along with food and wine while experiencing one of Loudoun County’s annual music traditions.
Bull Run Wine Festival
Annually, late September
What to Expect: Virginia wine tastings, live music, food trucks, and artisan vendors.
The Bull Run Wine Festival at The Winery at Bull Run offers a festive way to welcome the arrival of fall. Guests can sample local vintages, enjoy live music, browse local vendors, and grab food from onsite food trucks.
Festival of Leaves
Annually, October
What to Expect: Fall foliage, live entertainment, food, local vendors, and historic Front Royal.
Front Royal’s annual Festival of Leaves is a celebration of autumn in the Shenandoah Valley. The event features multiple stages of live entertainment, food vendors, local businesses, and activities throughout the town’s historic district. It’s an excellent choice for guests who want to experience the area’s fall scenery while exploring beyond the vineyards.
Virginia Wine & Garlic Festival
Annually, October
What to Expect: Virginia wine, garlic-inspired food, live music, and more than 100 vendors.
Held at Rebec Vineyards, the Virginia Wine & Garlic Festival combines Virginia wine with plenty of garlic-themed food and entertainment. The annual event features multiple stages of live music, garlic growers, food vendors, artisans, and activities for all ages. It’s a lively fall tradition for visitors looking for something a little different.
Powhatan’s Festival of the Grape
Annually, early October
What to Expect: Virginia wine, cider, beer and spirits, live music, food trucks, and craft vendors.
Powhatan’s Festival of the Grape celebrates Virginia’s beverage producers in the town’s historic Courthouse District. Along with regional pours, guests can enjoy cider, mead, beer, spirits, live music, food trucks, and handmade crafts. Now in its third decade, the festival remains a longstanding fall tradition.
George Washington’s Mount Vernon Fall Wine Festival
Annually, early October
What to Expect: Virginia wine, live music, and an evening at George Washington’s historic estate.
For guests extending their trip toward Northern Virginia, the Fall Wine Festival at George Washington’s Mount Vernon offers tastings from Virginia wineries on the estate’s east lawn overlooking the Potomac River. The event also provides an opportunity to explore Mount Vernon after hours, making it a memorable combination of wine and history.
Virginia Wine Month
Annually, October
What to Expect: Fall foliage, harvest season, winery visits, special events, and Virginia wines.
October is Virginia Wine Month, making it one of the best times to explore the Commonwealth’s vineyards. The annual celebration highlights Virginia’s wineries and harvest season, with special events, tastings, and experiences taking place throughout the state.
The Shenandoah Valley is particularly beautiful in autumn, when crisp temperatures and changing leaves create the perfect backdrop for a wine-country escape. Plan a few winery stops, enjoy a leisurely scenic drive, and return to Glen Gordon Manor for a relaxing evening.
Fall Thomas Jefferson Wine Festival
Annually, early November
What to Expect: Virginia wine, local food, live entertainment, and the historic setting of Poplar Forest.
Held at Thomas Jefferson’s Poplar Forest, this annual fall festival gives wine lovers another opportunity to explore Virginia’s wine culture while visiting a historic property. It’s a worthwhile option for guests planning a broader Virginia road trip beyond the Shenandoah Valley.
Gourmet Dining at Houndstooth Restaurant
Your Virginia wine experience doesn’t have to end when you return to Glen Gordon Manor. At Houndstooth Restaurant, guests can enjoy an intimate fine-dining experience alongside a carefully curated wine program.
Houndstooth has been recognized with Wine Spectator’s Best of Award of Excellence, honoring restaurants with impressive wine selections, standout producers and regions, and exceptional presentation and service. Glen Gordon Manor’s current recognition includes the Wine Spectator’s Best of Award of Excellence since 2024.
Pair your wine with Chef Dayn Smith’s seasonal cuisine, then retreat to your luxurious accommodations for a relaxing evening.
Plan Your Virginia Wine Country Getaway
From summer tastings to October’s Virginia Wine Month and colorful fall festivals, there are plenty of reasons to plan a getaway to Virginia wine country.
Make Glen Gordon Manor your home base and enjoy easy access to wineries, seasonal events, scenic drives, and the beauty of the Blue Ridge Mountains. After a day of exploring, return to the inn for gourmet dining, comfortable accommodations, and a peaceful setting designed for relaxation.
Book your stay at Glen Gordon Manor and start planning your Virginia wine country escape.
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