Dated Loudoun winery, brewery, cidery, and distillery events, generated from official venue and tourism calendars. Recurring live-music entries are expanded about eight weeks ahead when the site is seeded; one-off events drop after their date on the next deploy. Planning around a holiday? Pair the calendar with our confirmed holiday-hours guide.
Calendar generated July 10, 2026. Between deploys, always confirm the official event page before you drive out.
This weekend
Fri-Sun, Jul 10 – Jul 12, 2026, as of July 10, 2026.
Jason Frye at Old 690
Old 690 Brewing Company
Friday evening live music at Old 690 Brewing Company.
Add to calendar (opens in new tab)Download ICSVenue details — Jason Frye at Old 690Official page — Jason Frye at Old 690 (opens in new tab)
Key West Festival at Breaux
Breaux Vineyards
Breaux brings Key West energy to the vineyard for a one-day July festival.
Add to calendar (opens in new tab)Download ICSVenue details — Key West Festival at BreauxOfficial page — Key West Festival at Breaux (opens in new tab)
Scott Kurt at Creek's Edge
Creek's Edge Winery
Saturday live music at Creek's Edge Winery.
Add to calendar (opens in new tab)Download ICSVenue details — Scott Kurt at Creek's EdgeOfficial page — Scott Kurt at Creek's Edge (opens in new tab)
Dennis Wayland at Old 690
Old 690 Brewing Company
Saturday afternoon live music at Old 690 Brewing Company.
Add to calendar (opens in new tab)Download ICSVenue details — Dennis Wayland at Old 690Official page — Dennis Wayland at Old 690 (opens in new tab)
Live music weekends at Breaux Vineyards
Breaux Vineyards
Recurring Saturday and Sunday live music from 2-5pm with rotating performers on the official Breaux calendar.
Add to calendar (opens in new tab)Download ICSVenue details — Live music weekends at Breaux VineyardsOfficial page — Live music weekends at Breaux Vineyards (opens in new tab)
Neil McKillip at Creek's Edge
Creek's Edge Winery
Sunday live music at Creek's Edge Winery.
Add to calendar (opens in new tab)Download ICSVenue details — Neil McKillip at Creek's EdgeOfficial page — Neil McKillip at Creek's Edge (opens in new tab)
Summer Sundays Live Music at Dirt Farm
Dirt Farm Brewing
Dirt Farm runs its Summer Sundays Live Music Series every Sunday from 1-4pm, June through September.
Add to calendar (opens in new tab)Download ICSVenue details — Summer Sundays Live Music at Dirt FarmOfficial page — Summer Sundays Live Music at Dirt Farm (opens in new tab)
Youth Showcase at Old 690
Old 690 Brewing Company
Sunday afternoon youth showcase at Old 690 Brewing Company.
Add to calendar (opens in new tab)Download ICSVenue details — Youth Showcase at Old 690Official page — Youth Showcase at Old 690 (opens in new tab)
July 2026
Joey & the Waitress at Creek's Edge
Creek's Edge Winery
Saturday live music at Creek's Edge Winery.
Add to calendar (opens in new tab)Download ICSVenue details — Joey & the Waitress at Creek's EdgeOfficial page — Joey & the Waitress at Creek's Edge (opens in new tab)
Mark Cullinane at Old 690
Old 690 Brewing Company
Saturday afternoon live music at Old 690 Brewing Company.
Add to calendar (opens in new tab)Download ICSVenue details — Mark Cullinane at Old 690Official page — Mark Cullinane at Old 690 (opens in new tab)
Purcellville Wine and Food Festival
Fireman's Field Park
The 13th annual Purcellville Wine & Food Festival runs 2-8pm at Fireman's Field Park.
Add to calendar (opens in new tab)Download ICSOfficial page — Purcellville Wine and Food Festival (opens in new tab)
Melanie Pearl at Creek's Edge
Creek's Edge Winery
Sunday live music at Creek's Edge Winery.
Add to calendar (opens in new tab)Download ICSVenue details — Melanie Pearl at Creek's EdgeOfficial page — Melanie Pearl at Creek's Edge (opens in new tab)
Chris Hanks at Old 690
Old 690 Brewing Company
Sunday afternoon live music at Old 690 Brewing Company.
Add to calendar (opens in new tab)Download ICSVenue details — Chris Hanks at Old 690Official page — Chris Hanks at Old 690 (opens in new tab)
July Comedy Night at Breaux
Breaux Vineyards
Breaux hosts its July comedy-night event at the vineyard.
Add to calendar (opens in new tab)Download ICSVenue details — July Comedy Night at BreauxOfficial page — July Comedy Night at Breaux (opens in new tab)
Linda Andersen & Friends at Creek's Edge
Creek's Edge Winery
Saturday afternoon live music at Creek's Edge Winery.
Add to calendar (opens in new tab)Download ICSVenue details — Linda Andersen & Friends at Creek's EdgeOfficial page — Linda Andersen & Friends at Creek's Edge (opens in new tab)
Shane Gamble at Old 690
Old 690 Brewing Company
Saturday afternoon live music at Old 690 Brewing Company.
Add to calendar (opens in new tab)Download ICSVenue details — Shane Gamble at Old 690Official page — Shane Gamble at Old 690 (opens in new tab)
Mercy Creek at Creek's Edge
Creek's Edge Winery
Sunday live music at Creek's Edge Winery.
Add to calendar (opens in new tab)Download ICSVenue details — Mercy Creek at Creek's EdgeOfficial page — Mercy Creek at Creek's Edge (opens in new tab)
Doin' Time Country Classics at Old 690
Old 690 Brewing Company
Sunday afternoon live music at Old 690 Brewing Company.
Add to calendar (opens in new tab)Download ICSVenue details — Doin' Time Country Classics at Old 690Official page — Doin' Time Country Classics at Old 690 (opens in new tab)
Braham Noodles at Old 690
Old 690 Brewing Company
Friday evening live music at Old 690 Brewing Company.
Add to calendar (opens in new tab)Download ICSVenue details — Braham Noodles at Old 690Official page — Braham Noodles at Old 690 (opens in new tab)
August 2026
Live music weekends at Breaux Vineyards
Breaux Vineyards
Recurring Saturday and Sunday live music from 2-5pm with rotating performers on the official Breaux calendar.
Add to calendar (opens in new tab)Download ICSVenue details — Live music weekends at Breaux VineyardsOfficial page — Live music weekends at Breaux Vineyards (opens in new tab)
Summer Sundays Live Music at Dirt Farm
Dirt Farm Brewing
Dirt Farm runs its Summer Sundays Live Music Series every Sunday from 1-4pm, June through September.
Add to calendar (opens in new tab)Download ICSVenue details — Summer Sundays Live Music at Dirt FarmOfficial page — Summer Sundays Live Music at Dirt Farm (opens in new tab)
BBQ & Bluegrass at Breaux
Breaux Vineyards
A barbecue-and-bluegrass day at Breaux; the official listing notes free admission.
Add to calendar (opens in new tab)Download ICSVenue details — BBQ & Bluegrass at BreauxOfficial page — BBQ & Bluegrass at Breaux (opens in new tab)
August Comedy Night at Breaux
Breaux Vineyards
Breaux hosts its August comedy-night event at the vineyard.
Add to calendar (opens in new tab)Download ICSVenue details — August Comedy Night at BreauxOfficial page — August Comedy Night at Breaux (opens in new tab)
September 2026
Bluemont Crush With Us
Bluemont Vineyard
Grape-stomping harvest event on September weekends at Bluemont Vineyard.
Add to calendar (opens in new tab)Download ICSVenue details — Bluemont Crush With UsOfficial page — Bluemont Crush With Us (opens in new tab)
LoCo Fest at 868 Estate
868 Estate Vineyards
868 Estate Vineyards’ marquee early-fall music festival, LoCo Fest — an all-day (noon–9pm) day of live music at the Purcellville vineyard.
Add to calendar (opens in new tab)Download ICSVenue details — LoCo Fest at 868 EstateTickets — LoCo Fest at 868 Estate (opens in new tab)Official page — LoCo Fest at 868 Estate (opens in new tab)
Bear Chase Oktoberfest
Bear Chase Brewing Company
Bear Chase's annual Oktoberfest at the Bluemont brew barn — market vendors, live music, and their gold-medal Oktoberfest Marzen lager.
Add to calendar (opens in new tab)Download ICSVenue details — Bear Chase OktoberfestOfficial page — Bear Chase Oktoberfest (opens in new tab)
Bluemont Fair
Bluemont Community Center
Traditional country fair in the village of Bluemont.
Add to calendar (opens in new tab)Download ICSOfficial page — Bluemont Fair (opens in new tab)
Lovettsville Oktoberfest
Downtown Lovettsville
Town-wide German-heritage Oktoberfest festival in Lovettsville.
Add to calendar (opens in new tab)Download ICSOfficial page — Lovettsville Oktoberfest (opens in new tab)
Leesburg Airshow
Leesburg Executive Airport
Free late-September airshow at Leesburg Executive Airport with aerial performances and ground attractions.
Add to calendar (opens in new tab)Download ICSOfficial page — Leesburg Airshow (opens in new tab)
October 2026
Great Country Farms Fall Pumpkin Harvest
Great Country Farms
Great Country Farms’ month-long Fall Pumpkin Harvest in Bluemont — pick-your-own pumpkins, corn maze and apple harvest, next door to Bear Chase and Dirt Farm.
Add to calendar (opens in new tab)Download ICSOfficial page — Great Country Farms Fall Pumpkin Harvest (opens in new tab)
Waterford Fair
Historic Waterford Village
Virginia's oldest crafts fair, early October, in historic Waterford.
Add to calendar (opens in new tab)Download ICSOfficial page — Waterford Fair (opens in new tab)
Loudoun Wine Awards
Lansdowne Resort & Spa
October gala honoring Loudoun’s Winemaker / Winegrower / Wine Ambassador of the Year; Grand Tasting at 6pm at Lansdowne Resort.
Add to calendar (opens in new tab)Download ICSOfficial page — Loudoun Wine Awards (opens in new tab)
Harvest Festival at Breaux
Breaux Vineyards
Breaux Vineyards’ fall Harvest Festival weekend at the Purcellville estate.
Add to calendar (opens in new tab)Download ICSVenue details — Harvest Festival at BreauxOfficial page — Harvest Festival at Breaux (opens in new tab)
November 2026
LoCo Wine Festival – Fall
Old Farm Winery at Hartland
Fall edition of the Loudoun wine festival at Old Farm Winery at Hartland, with wine tastings, food trucks, live music, and an artisan market.
Add to calendar (opens in new tab)Download ICSOfficial page — LoCo Wine Festival – Fall (opens in new tab)
December 2026
Christmas in Middleburg Parade
Downtown Middleburg
December holiday parade and festivities in Middleburg.
Add to calendar (opens in new tab)Download ICSOfficial page — Christmas in Middleburg Parade (opens in new tab)
Leesburg Holiday Tree Lighting
Town Green (Leesburg Town Hall)
Town of Leesburg holiday tree lighting on the Town Green — lights, live music, and holiday characters, from 6pm. The Christmas & Holiday Parade is a separate event a week later.
Add to calendar (opens in new tab)Download ICSOfficial page — Leesburg Holiday Tree Lighting (opens in new tab)
Leesburg Holiday Parade
Ida Lee Park
Leesburg’s Christmas & Holiday Parade — Santa and floats down King Street through Historic Downtown, starting at Ida Lee Park, from 6pm (rain date Dec 13).
Add to calendar (opens in new tab)Download ICSOfficial page — Leesburg Holiday Parade (opens in new tab)
Seasonal planning notes
Annual and seasonal programs without confirmed future dates yet. These stay here as planning leads, but only dated items above become Event structured data.
4th of July at Ida Lee Park
Leesburg's Independence Day celebration at Ida Lee Park.
Official page — 4th of July at Ida Lee Park (opens in new tab)
Acoustic on the Green
Free Town of Leesburg Summer JAMS concerts on most Saturdays, June 6-August 22, 2026, 7-8:30pm on Town Green; no concert July 4 or August 8.
Bluemont Lighting of the Vines
Bluemont Vineyard
About 15,000 holiday lights at Bluemont Vineyard. The 2025 Launch Party ran Fri–Sat, Nov 28–29 (Thanksgiving weekend), 4–7pm; 2026 dates are not yet announced.
Venue details — Bluemont Lighting of the VinesOfficial page — Bluemont Lighting of the Vines (opens in new tab)
Bluemont TrueBlue / Sunset Saturdays
Bluemont Vineyard
Bluemont Vineyard's summer sunset concert series.
Venue details — Bluemont TrueBlue / Sunset SaturdaysOfficial page — Bluemont TrueBlue / Sunset Saturdays (opens in new tab)
Brewery Anniversary Parties & Seasonal Releases
Recurring anniversary parties and seasonal releases; track via Visit Loudoun brewery page and LCBA Eventbrite.
Official page — Brewery Anniversary Parties & Seasonal Releases (opens in new tab)
Fall & Spring Farm Tours
Self-guided tours of ~40 farms including wineries and breweries, held both spring and fall.
Harvest Dinners & Yoga in the Vines
Harvest dinners, 'yoga in the vines,' and guest-chef farm dinners across wineries.
Official page — Harvest Dinners & Yoga in the Vines (opens in new tab)
King Street Halloween Parade
October Halloween parade through downtown Leesburg (Kiwanis Club of Leesburg). 2025 (69th annual) ran Thursday, Oct 30, 6pm; the 2026 (70th annual) date is not yet announced.
Official page — King Street Halloween Parade (opens in new tab)
Leesburg First Friday
Monthly downtown gallery walk with shops/restaurants open late and wine tastings.
Leesburg Flower & Garden Festival
3rd weekend of April; free, ~150 vendors, rooftop beer garden.
Official page — Leesburg Flower & Garden Festival (opens in new tab)
LoCo Ale Trail Digital Passport
Free beer check-in rewards program via LoyalBrew across Loudoun breweries; sign up any time.
Official page — LoCo Ale Trail Digital Passport (opens in new tab)
LoCo Wine Festival – Spring
Late-April edition of the twice-yearly Loudoun wine festival.
Official page — LoCo Wine Festival – Spring (opens in new tab)
Loudoun Beer Awards / Brewers Choice Awards
Early-February LCBA awards — Brewer of the Year, Best of Loudoun Beer, etc.
Official page — Loudoun Beer Awards / Brewers Choice Awards (opens in new tab)
Loudoun County Barrel Tasting
Multi-winery weekend of barrel/pre-release tastings.
Official page — Loudoun County Barrel Tasting (opens in new tab)
Loudoun Pours to Explore
Loudoun Wineries & Winegrowers Association tasting series; next official listing is November 14, 2026, 6-8pm, highlighting Sauvignon Blanc and Cabernet Franc. Location was not published on the event page, so this remains a seasonal planning note until the physical venue is confirmed.
Middleburg Spring Races
Spring steeplechase horse-racing event in Middleburg.
Polo in the Park at Morven Park
Summer polo matches at Morven Park, Leesburg.
Official page — Polo in the Park at Morven Park (opens in new tab)
Pride in the Vines
Month-long June Pride wine passport (Loudoun Wineries & Winegrowers Assoc.); collect 10 stamps for a prize drawing.
Quattro Goomba's Oktoberfest
Quattro Goomba's Brewery
Oktoberfest at Quattro Goomba's, Aldie. 2025 ran Sunday, Oct 12; the 2026 date is not yet announced on the winery/brewery's own site.
Venue details — Quattro Goomba's OktoberfestOfficial page — Quattro Goomba's Oktoberfest (opens in new tab)
Stone Tower Harvest Dinner
Stone Tower Winery
Stone Tower Winery’s annual Harvest Dinner in Leesburg. 2025 ran Friday, Nov 14 (Vineyard View Ballroom); the 2026 date is not yet announced.
Venue details — Stone Tower Harvest DinnerOfficial page — Stone Tower Harvest Dinner (opens in new tab)
TASTE Leesburg
Downtown Leesburg culinary festival; the Town of Leesburg lists the 2026 edition for Saturday, August 8. Kept undated here until the event page publishes a stable physical address for JSON-LD and ICS.
Tarara Summer Concert Series
Marquee Saturday vineyard concerts at Shadow Lake, Leesburg, ~Memorial Day to late September. 2026 is the series’ final season as the winery winds down — confirm each date before planning around it.
Official page — Tarara Summer Concert Series (opens in new tab)
Virginia Craft Beer Cup
Statewide summer craft-beer competition relevant to Loudoun brewers.
Virginia Craft Beer Month
Statewide August celebration; track Loudoun brewery events via Visit Loudoun / LCBA.
Official page — Virginia Craft Beer Month (opens in new tab)
Virginia Governor's Cup (judging at Breaux)
Breaux Vineyards
Premier VA wine competition (670+ wines); judging physically held at Breaux Vineyards, Purcellville, in January.
Venue details — Virginia Governor's Cup (judging at Breaux)Official page — Virginia Governor's Cup (judging at Breaux) (opens in new tab)
Virginia Wine Country Half Marathon & Wine Festival
Doukénie Winery
Late-May race paired with a post-run wine festival.
Venue details — Virginia Wine Country Half Marathon & Wine FestivalOfficial page — Virginia Wine Country Half Marathon & Wine Festival (opens in new tab)
Virginia Wine Month
Statewide October celebration; 40+ Loudoun wineries participate — peak season.
Wheatland Spring Oktoberfest
Wheatland Spring Farm + Brewery
Wheatland Spring Farm + Brewery’s annual Oktoberfest in Waterford. 2025 (7th annual) ran Sept 13–14; the 2026 date is not yet announced.
Venue details — Wheatland Spring OktoberfestOfficial page — Wheatland Spring Oktoberfest (opens in new tab)
Wine Trail Guide
Visit Loudoun's self-guided wine planning tool, promoted heavily during October Virginia Wine Month (#DCsWineCountry).
Winery Holiday Tastings & Wreath-Making
Holiday tastings, wreath-making and mulled wine at many wineries through the season.
Official page — Winery Holiday Tastings & Wreath-Making (opens in new tab)
Keep exploring
Browse our ranked best-of lists or line up a safe, chauffeured way to tour the county.