This weekend in Montgomery County is shaping up to be one of the busiest of the fall, with festivals, parades, live music, food, and community celebrations taking place across the area. From family-friendly activities and cultural performances to beer gardens, bar crawls, and long-standing neighborhood traditions, there will be no shortage of ways for residents to enjoy the season and come together with their communities.
Bethesda’s biggest food festival is back this fall. The 33rd annual Taste of Bethesda takes place on Saturday, October 4, 2025, from 11 a.m. to 4 p.m. in the Woodmont Triangle, bringing together some of the area’s best restaurants, live entertainment, family activities, and more. Additional information can be found here.
The second annual Crowntoberfest craft beer and music festival is set to take place on Saturday, October 4th from 12-6PM at Crown Park in Downtown Crown. Hosted by Downtown Crown Wine & Beer and local musicians Kenny & Joel, the event offers a full day of local live music, food from Taco Bar, and beer. Last year, over 500 people attended the event. Additional information can be found here.
The 2025 Germantown October Fest will take place on Saturday, October 4, 2025, along Century Boulevard and the BlackRock Center for the Arts lawn. The parade itself begins at 11:30am. The free, family-friendly event will feature live music from Nine Days, a parade with the Commanders Command Force and Major Tuddy, a beer garden, food trucks, artisan vendors, a free children’s carnival, and cultural performances. Additional information can be found here.
The Kentlands Bar Crawl is back for its second outing of 2025, bringing drinks, neighbors, and community spirit together in Gaithersburg’s Kentlands neighborhood. The fall edition will take place on Saturday, October 4, from 5 p.m. to 10 p.m., with proceeds benefiting Comfort Cases, a local nonprofit that supports children entering foster care. Additional information can be found here.
Montgomery Village’s Fall Festival will take place this year on Saturday, October 4 from 11am-2:30pm at North Creek Community Center (20125 Arrowhead Road). The event will feature food trucks, games, a petting zoo, and the annual Great Pumpkin Race. Additional information can be found here.
North Bethesda’s PIKEtoberfest will take place on Sunday, October 5, from 12 p.m. to 4 p.m. at Pike & Rose (11580 Grand Park Avenue). The free community event will feature live music, entertainment, and a variety of activities for all ages. Additional information can be found here.
The popular Takoma Park Street Festival returns for its 44th year of music, vendors, food and fun in Takoma Park. This year’s festival takes place on Sunday, October 5, 2025 from 10:00am-5:00pm on Carroll Avenue in Takoma Park, MD to Carroll Street, NW in Takoma, DC. Additional information can be found here.
Montgomery Parks has announced the reopening of Wheaton Ice Arena on Saturday, October 4, 2025. The rink is ready to glide back into action after a five-month closure to install a new refrigeration system. Additional information can be found here.
