Wine and beer events in the DMV
Wine and beer across the DMV: winery and brewery events, tastings, releases, festivals and taproom happenings.
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Friday, October 2 TodayJump to Sat Oct 3
Calvert Woodley Wine World Tour6pm$404200 Connecticut Ave NW, Washington, DC 20008Guided tasting of wines from around the world hosted by Calvert Woodley in the UDC Student Center ballroom. $35 early bird, $40 after Sep 27.
A Toast to Maryland! Harvest Dinner at Windridge VineyardsAll day, day 1 of 2, Oct 2 to 3$12515700 Darnestown Rd, Darnestown, MD 20874Windridge 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%.
Saturday, October 3 TomorrowJump to Thu Oct 8
Frederick's Oktoberfest 25th Anniversary11am to 10pm, day 2 of 2, Oct 2 to 3797 E Patrick St, Frederick, MD 21701Frederick'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.
Vienna Oktoberfest11am to 7pmFree131 Church St NE, Vienna, VA 22180Town-run Oktoberfest on Church Street with German beer, food, live music, and vendors. Free admission; drink tickets $8 each or 4 for $30.
Rosslyn Fall Fest1 to 6pmFree1401 Wilson Blvd, Arlington, VA 22209Free fall festival at the NOW pop-up park featuring local beer, cider, and wine alongside food vendors and family activities.
Oktoberfest at The Wharf2 to 6pmFree101 District Square SW, Washington, DC 20024Free Oktoberfest on District Pier with German beer, brats, live music, and games on the Southwest waterfront.
Harvest Party: Grape Stomp, Vineyard Tour, and Wine Pairings5 to 10pm$49.8718035 Raven Rocks Road, Bluemont, VA 20135Evening 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.
A South African Winemaker's Dinner with Thomas Webb7 to 9pm$99.992415 Wilson Boulevard, Arlington, VA 22201One-night-only seated multi-course dinner with South African winemaker Thomas Webb, each course paired with his wines. $99.99 per guest, seating limited.
Mount Airy Main Street OktoberfestAll dayMain Street, Mount Airy, MD 21771Main 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.
Thursday, October 8 Jump to Fri Oct 9
The Vineyard Table at Black Ankle VineyardsAll day, one of 3 dates$13214463 Black Ankle Road, Mount Airy, MD 21771Black Ankle Vineyards hosts an intimate three-course wine-pairing dinner on the second Thursday of each month. Chef Tony's seasonal, locally sourced menu is paired course by course with Black Ankle wines; the October menu features roasted beet salad with 2023 Phyllite, Dijon pork loin with house Syrah, and poached pears with 2024 Merlot Rose.
Friday, October 9 Jump to Sat Oct 10
Mount Vernon Fall Wine Festival6 to 9pm, day 1 of 3, Oct 9 to 113200 Mount Vernon Memorial Hwy, Mount Vernon, VA 22121Evening 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).
Saturday, October 10 Jump to Sun Oct 11
Autumn Reggae Wine and Music Festival 2026 at Linganore Winecellars10am to 6pm, day 1 of 2, Oct 10 to 11$4513601 Glissans Mill Rd, Mount Airy, MD 21771Linganore 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.
Snallygaster 202612 to 6pm$75Pennsylvania Ave NW, Washington, DC 20004Beer 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.
Settle Down Easy Fall Pierogi Fest12 to 7pm$23.182822 Fallfax Drive, Falls Church, VA 22042Fall festival at the Falls Church brewery pairing pierogies with house-brewed beer, with live music and fall activities. Tickets from $23.18 on Eventbrite.
Germantown October Fest 2026All dayFree12901 Town Commons Drive, Germantown, MD 20874Germantown 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.
Sunday, October 11 Jump to Fri Oct 16
33rd Annual Gaithersburg OktoberfestAll dayFree311 Kent Sq Rd, Gaithersburg, MD 20878The 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.
Friday, October 16 Jump to Sat Oct 17
DC Wine Fest Fall EditionAll day, day 1 of 2, Oct 16 to 17$611309 5th St NE, Washington, DC 20002Multi-session wine tasting at Dock 5 at Union Market with wineries pouring samples; early admission available. 21 and over. Session times not listed on the organizer site.
Saturday, October 17 Jump to Sun Oct 18
6th Annual Beer Festival at Bear Chase Brewing Company11am to 4pm$4533665 Bear Chase Lane, Bluemont, VA 20135Bear Chase Brewing Company hosts its sixth annual beer festival with tastings from local craft breweries in one place. Ticket includes a souvenir tasting glass and 10 tasting tickets for pours of fall and seasonal beers, plus live music. 21 and over; the brewery stays open for regular business during the event.
Shipgarten Oktoberfest Renaissance Festival1 to 6pmFree7581 Colshire Dr, McLean, VA 22102Oktoberfest with a Renaissance theme at Shipgarten's beer garden: German beers, food, live entertainment, and themed activities. Free entry.
The Sommelier's Table: Northern Italy2pm$1103623 Grove Lane, Delaplane, VA 20144Intimate guided tasting at Barrel Oak Winery exploring the distinctive wines of Northern Italy. Led by the estate sommelier and a representative from wine importer Massanois, featuring small-production wines rarely found on retail shelves, with first access to purchase the featured bottles.
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