wkndSun Oct 11 2026, all dayFreeKentlandsThe City of Gaithersburg's 33rd Oktoberfest fills the Kentlands with multiple stages of Bavarian music and dancing, beer, mead, cider, non-alcoholic beer, food, artisan vendors, and fall family activities. Admission, parking, and shuttle service from 101 Orchard Ridge Drive are all free; crowds have topped 30,000 in past years.
Sun Oct 11 2026, 6 to 9pmGeorge Washington's Mount VernonEvening wine festival on the grounds of George Washington's Mount Vernon with Virginia wineries pouring tastings, live music, and the mansion lit at night. Ticket prices vary by evening (Fri $62, Sat $66, Sun $51).
Sun Oct 11 2026, 10am to 6pm$45Linganore WinecellarsLinganore Winecellars marks 50 years with a two-day fall festival pairing reggae bands with wine. General admission includes unlimited sampling of 19 Linganore wines, a keepsake tasting glass, craft beer from Red Shedman Brewery, seasonal specialty drinks, and 40+ boutique vendors. Live music runs 10 AM to 6 PM each day; kids 17 and under attend free.
Sat Oct 10 2026, all dayFreeGermantown Town CenterGermantown Town Center hosts a free one-day October Fest with a MoCo Show beer garden, drag beer garden bingo (separate ticket), live music headlined by Nappy Roots, international food vendors, a parade, artisan market, and a kids carnival. No ticket is needed to attend; RSVP enters you to win a local prize pack.
Sat Oct 10 2026, 12 to 7pm$23.18Settle Down Easy Brewing – Falls ChurchFall festival at the Falls Church brewery pairing pierogies with house-brewed beer, with live music and fall activities. Tickets from $23.18 on Eventbrite.
Sat Oct 10 2026, 12 to 6pm$75WashingtonBeer festival on Pennsylvania Avenue NW with hundreds of craft beers from regional and national breweries, plus food vendors and live music. VIP entry at noon, general admission 2 to 6 pm.
Sat Oct 3 2026, all dayMount AiryMain Street shuts down for Mount Airy's annual Oktoberfest, a one-day community tradition with cold beer, food vendors, live music, and local shops open along the historic district. Organized by the Mount Airy Main Street Association; admission and ticket pricing were not posted on the official page.
Sat Oct 3 2026, all day$125DarnestownWindridge Vineyards celebrates harvest with a six-course Maryland-inspired dinner at a communal candlelit table, paired with its estate-grown Piedmont Plateau wines. Chef Jeff Palmer cooks regional dishes; wine pairings, cocktails, and gratuity are included in the ticket. Seats are limited, and wine club members save 10%.
Sat Oct 3 2026, 5 to 10pm$49.87BluemontEvening harvest party at a mother-daughter-owned boutique winery in Bluemont. Includes a guided vineyard and property tour, a traditional grape stomp, and three curated wine and food pairings led by the head sommelier. 21 and over.
Sat Oct 3 2026, 11am to 10pmFrederickFrederick's 25th annual Oktoberfest at the Frederick Fairgrounds. German food, beer, wine and cider, live music and dancing, with proceeds supporting Frederick County community causes. Friday is 21+; Saturday is all ages. Admission about $25 Friday, $22 Saturday GA.
Sat Oct 3 2026, 7 to 9pm$99.99ArlingtonOne-night-only seated multi-course dinner with South African winemaker Thomas Webb, each course paired with his wines. $99.99 per guest, seating limited.
Sat Oct 3 2026, 11am to 7pmFreeViennaTown-run Oktoberfest on Church Street with German beer, food, live music, and vendors. Free admission; drink tickets $8 each or 4 for $30.
Sat Oct 3 2026, 2 to 6pmFreeWashingtonFree Oktoberfest on District Pier with German beer, brats, live music, and games on the Southwest waterfront.
Sat Oct 3 2026, 1 to 6pmFreeArlingtonFree fall festival at the NOW pop-up park featuring local beer, cider, and wine alongside food vendors and family activities.
Fri Oct 2 2026, 6pm$40WashingtonGuided tasting of wines from around the world hosted by Calvert Woodley in the UDC Student Center ballroom. $35 early bird, $40 after Sep 27.
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