wkndSun Oct 11 2026, all day$110The PentagonOne of the world's largest 10-mile races, starting and finishing at the Pentagon and passing DC's monuments. Proceeds support Army Family and MWR programs; a youth run follows for kids 12 and under.
Sun Oct 11 2026, all dayClifton57th annual Clifton Day turns the tiny historic town of Clifton into a bustling fall marketplace. More than 150 artisans, antiques, and food vendors line the streets, with live music on multiple stages, a beer and wine garden, pony rides, and children's activities. Free admission. It is the only day of the year the VRE train stops in Clifton, with a free ride into town.
Sun Oct 11 2026, 6 to 9pm$51Mount VernonAnnual evening wine festival on the east lawn of George Washington's estate, overlooking the Potomac River at sunset. Unlimited samples from Virginia wineries, live blues music, after-hours mansion tours including the wine cellar, and a commemorative glass to take home. Bring a blanket or lawn chair.
Sun Oct 11 2026, 9am to 5pmFreeThurmont Community ParkOne of the East Coast's largest outdoor craft shows draws 100,000 visitors to Thurmont for juried arts and crafts amid peak Catoctin foliage. Admission is free; parking costs extra; runs rain or shine.
Sun Oct 11 2026, 12 to 5pmFreeKentlandsThe City of Gaithersburg's 33rd annual Oktoberfest fills the Kentlands (Arts Barn, Kentlands Mansion, Village Green, Main Street) with traditional Bavarian music and dancing, a business expo, artisan vendors, fall kids activities, and German food with beer, mead, and cider. Free admission, parking, and shuttle.
Sat Oct 10 2026, 4 to 7pmFreeMaydale Nature ClassroomA cozy evening fall celebration at Maydale Nature Classroom with pumpkin painting, live music, a campfire, and guided nature discovery. Dogs are welcome, with a costume contest, cutest-trick talent show, and doggy musical chairs. Native trees and shrubs are also for sale. Free; costumes encouraged.
Sat Oct 10 2026, 12 to 6pm$75WashingtonThe East Coast's biggest craft beer festival returns to Pennsylvania Avenue for its 14th year. More than 450 rare and small batch beers, ciders, gravity kegs and bottle pours from 166 American and international producers, plus food trucks and two stages of live music with the Capitol as the backdrop. The festival is a fundraiser for Arcadia Food. Note: general admission is sold out per the organizer's site; VIP remains listed.
Sat Oct 10 2026, 2 to 6pmFreeWashingtonA brand new neighborhood music festival for its first year on the Hill. Front porches, stoops and yards across Capitol Hill, Hill East, Lincoln Park and Barracks Row become small outdoor stages for an afternoon of live bands. Walk between porches, bring neighbors, and catch local acts. Free all afternoon; Sunday, October 11 is the rain date.
Sat Oct 10 2026, 11am to 5pmFreeGermantown Town CenterGermantown Town Center's free fall festival with a community parade led by the Seneca Valley Marching Band, live music headlined by Nappy Roots, a MoCo Show beer garden, BlackRock artisan market, international food vendors, kids carnival, and a 90s-inspired Halloween hangout for families. RSVP online enters you in a prize drawing.
Sat Oct 10 2026, 10am to 5pmFreeOld Town FairfaxThe 50th annual fall festival fills the streets of Old Town Fairfax. More than 400 arts, crafts, food, and information vendors, three stages of music and entertainment including a Taylor Swift tribute band, children's activities and rides, plus beer gardens. Free admission; fees for kids' rides. Free shuttle from the GMU Rappahannock deck and Fairfax High School.
Thu Oct 8 2026, 6 to 9pmFreeWashingtonThe National Gallery of Art's after-hours program goes spooky for October. Hear DC funk-pop band Oh He Dead, hunt for the gallery's eeriest artwork, and make a creepy creation to take home. Free, but registration ran through a lottery (September 28 to October 1). Costumes welcome; full-face masks are not allowed inside.
Sun Oct 4 2026, 10am to 5pm$20WaterfordThe 82nd annual Waterford Fair takes over the National Historic Landmark village of Waterford. Heritage and contemporary artisans demonstrate crafts and sell juried wares, with historic home and garden tours, Tent Talks on Loudoun history, Americana and old-time music, kids' activities and a scavenger hunt, plus Loudoun wine, cider, and beer. One all-weekend pass covers all three days; kids 12 and under are free.
Sun Oct 4 2026, 10am to 5pmFreeTakoma ParkThe 45th annual Takoma Park Street Festival closes Carroll Avenue for a day of 185+ vendor booths, 18 local bands across three stages, food trucks, and the neighborhood's shops and cafes. Rain or shine, free to attend, three blocks from the Takoma Metro station.
Sat Oct 3 2026, 11am to 7pmFreeViennaFree one-day Oktoberfest on historic Church Street. Three stages of live German and American music, beer and wine gardens pouring local craft brews, a global food court, an artisan market, and a free kids zone on the Town Green. Keg tapping at 11am, stein-holding contest at 3pm, best-dressed awards at 4pm. Free shuttle from Vienna Metro and James Madison High School.
Sat Oct 3 2026, 10am to 6pmFreeAlexandriaThe 31st annual Art on the Avenue takes over ten blocks of Mount Vernon Avenue in Del Ray. More than 300 artists and makers show and sell jewelry, woodwork, pottery, glass, paintings, and fabric art, with live music on multiple stages, international food vendors, and kids' activities like pumpkin painting and scarecrow stuffing. Free.
Sat Oct 3 2026, 2 to 6pmFreeWashingtonDC's biggest Oktoberfest celebration takes over The Wharf's waterfront with the 14th annual Wiener 500 Dachshund Dash as the centerpiece. Watch dachshunds sprint down District Pier, then stick around for the stein hoisting championship, a best dressed contest, DJ sets, Sam Adams Octoberfest beer and adoptable dogs from local rescues. Free to attend; race entry fees benefit Rural Dog Rescue.
Sat Oct 3 2026, 11am to 4pmFreeBethesdaBethesda's long-running downtown food festival takes over Woodmont Triangle with small plates from more than 45 local restaurants, from Turkish kebabs to cupcakes and ramen. Four stages host live music and cultural performances through the afternoon, plus a kids area with face painting and crafts. Admission is free; tasting portions are bought with on-site tickets (five for $10), each dish costing one to four tickets.
Sat Oct 3 2026, 11am to 4pm$20DerwoodMontgomery Parks' annual fall day at the Agricultural History Farm Park with hayrides, pumpkin painting, live music, kids crafts, historic games, farm animals, and food trucks. Demos include sheepdog herding, blacksmithing, and a sawmill, plus appearances by the Park Police. Rain or shine; $20 per car, cash only; food and some activities cost extra. Dogs are not permitted.
Sat Oct 3 2026, 10am to 3pmFreeKetteringOld Maryland Farm's annual fall festival with a pumpkin patch, open barn visits with horses and other farm animals, and games like pumpkin bowling, hobby horse races, ring toss, and lasso the steer. Kids can work a bingo card of activities for a prize. Local craft vendors plus food and produce trucks round out the day. Free admission.
Sat Oct 3 2026, 11am to 2:30pmFreeMontgomery VillageMontgomery Village's quirky fall tradition: racers bolt wheels through decorated pumpkins and face off in single-elimination heats for the Pumpkin Race Championship Trophy, with awards for scariest, prettiest, and most creative designs. The surrounding Fall Festival adds live music, food, and children's activities. Free to watch; race kits sold at the MVF office.
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