As summer winds down, the DMV comes alive with incredible crisp-weather energy! September marks the grand kickoff to fall festival season, bringing an incredible lineup of vibrant food and drink celebrations, live music under open skies, artisan markets, and unique local traditions. Dive into our top event picks across DC, Maryland, Virginia, and West Virginia to start filling your autumn calendar with unforgettable experiences.
WASHINGTON, DC
NSO Annual Labor Day Concert | September 6
The National Symphony Orchestra’s annual free Labor Day weekend concert returns, this year at DAR Constitution Hall! Led by conductor Enrico Lopez-Yañez, the NSO will perform a program of American favorites featuring vocalist Ender Thomas. The concert will also include Karen LeFrak’s American Promise, narrated by Dr. Alveda King. A must-see celebration!
Free Admission
DC Jazzfest | September 2-6
The Wharf & Other DC Locations
DC JazzFest brings national and local musicians to a range of venues all over the city, including The Wharf. Some concerts are free; most are ticketed. Lineup headliners for 2025 include Branford Marsalis, Eddie Palmieri, Ron Carter, Lalah Hathaway, the String Queens, the John Scofield Trio, Sun Ra Arkestra, and Matthew Whitaker. Some performances are free.
DC Bike Ride | September 12
If you’re looking for fun activities in the District this fall, you’ve found a gem with DC Bike Ride. With a family-friendly course, the event is one of the biggest celebrations of cycling in DC and offers a unique experience to its participants, winding riders through city streets and by monuments and memorials. The 20-mile excursion welcomes riders over the age of three and includes a Finish Festival with food, music and fun activities.
DC State Fair | September 6
This free, one-day festival puts an urban spin on agricultural traditions, showcasing the District's local agricultural, culinary, and creative talents. Visitors can look forward to live entertainment, hands-on workshops, and over 50 hyper-local competitions judging everything from homegrown tomatoes to the best D.C. mumbo sauce. The event is easily accessible by public transit, located just a short walk from the Gallery Place–Chinatown and Mount Vernon Square metro stations.
National Gallery Nights | Starting September 10
National Gallery of Art, East Building
One of the city’s most popular museums comes to life after hours with themed evenings featuring music, live performances, artmaking, pop-up talks, and more. Due to high demand, admission is offered through a lottery system the week before each event, with a limited number of additional passes available at the East Building entrance beginning at 5:30 p.m. on a first-come, first-served basis.
Celebrate Oktoberfest in the District | Mid September though Early October
Beginning in mid-September and extending into October, DC beer enthusiasts break out their lederhosen and dirndls to observe Oktoberfest with German beer, bites and live music. Locations across the city will participate, including a few annually recurring favorites: Bluejacket serves weissbiers, schwarzbiers and helles lagers from the keg, Wunder Garten hosts its Pridetoberfest LGBTQ+ party and The Wharf goes all out for a weekend with Polka on the Pier, a Stein Hosting Competition and the thrilling Dachshund Dash.
All Things Go Music Festival | September 25-27
10475 Little Patuxent Pkwy Columbia, MD 21044
You'll want to plan ahead for this popular festival that has sold out the last few years. Hosted at Merriweather Post Pavilion, the event features two stages with 45+ artists performing, thoughtfully curated food experiences, and interactive art.
MARYLAND
World’s Largest Pickle Party 2026 | September 19
Pickle lovers can sample more than 100 varieties at this wonderfully unconventional food festival. The celebration includes pickle-inspired dishes, live country music, competitions, games, a Pickle Rave, and a 25-foot pickle jar known as “The Big Brine.”
Bay Bridge Paddle | September 13
Sandy Point State Park, Annapolis
This year’s paddle will be in the warm waters of the Chesapeake Bay with race courses for all levels from beginner to advanced! Enjoy live music, craft beer, and good eats while participating in beach activities.
The Great Frederick Fair | September 18-26
This annual fair includes a carnival midway, nightly grandstand entertainment, international award-winning agricultural exhibits, activities, and of course fantastic food!
Tickets for Advanced Gate | Tickets for Concerts and Events (includes general admission)
Kunta Kinte Heritage Festival | September 26
Navy-Marine Corps Memorial Stadium, Annapolis
Celebrate African and African American culture at this vibrant Annapolis festival featuring live music, dance, storytelling, artisan vendors, cultural demonstrations, and food from throughout the African diaspora. The festival honors the legacy of Kunta Kinte while bringing thousands of visitors together for an afternoon of history, culture, and community.
Free Entry
VIRGINIA
Leesburg First Friday | September 5
Downtown Historic Leesburg
Stroll through Historic Downtown Leesburg on the first Friday of each month and visit shops, restaurants, art galleries, and offices to enjoy live music, art exhibits, wine tastings, book signings, shopping, and dining at local small businesses. Free & fun!
Rosslyn Jazz Fest | September 12
Arlington, Virginia’s most popular free outdoor music festival returns Saturday the 12th at Gateway Park! Join the Rosslyn BID and Arlington Arts at the 34th Rosslyn Jazz Fest for an afternoon of music, community, food trucks, yard games, and more.
Free Admission | Registration is recommended
Vesta Settlements Charity Poker Tournament | September 9
Come eat, drink, mingle, play all for charity! We are proud supporters of this annual event and we need you to reach our goal. By joining us, you’ll be supporting Loudoun Habitat for Humanity’s mission of making homeownership a reality for everyone.
50th Annual Falls Church Festival | September 19
This family-fun event features The Taste of Falls Church, live music, children’s entertainment, and booths from local crafters, businesses, and civic organizations.
Free Admission
Mount Vernon Colonial Market & Fair | September 19 & 20
Experience an 18th-century marketplace at George Washington’s beautiful Mount Vernon Estate with traditional handcrafted wares, live colonial-era music, and demonstrations of period crafting techniques. The fair is included with general admission.
Chillin’ on Church Block Party | September 18
Chillin’ on Church is the hottest block party around and fun for the whole town! Held every third Friday, June through September on historic Church Street, the event includes food, local beer and wine, music, and family-friendly activities. Be sure to bring a valid ID, as it is required.
Free Admission
Bluemont Fair | September 19 & 20
Spend the day wandering through the 200-year-old village, browse artisan crafts, and enjoy local wine, beer, and food. Live music and fun activities are available for the kids.
Admission $10 | Children 9 & Under are Free | No Pets Allowed
84th Historic Alexandria Homes Tour | September 26
Since 1997, The Twig has welcomed visitors to this annual event, featuring a self-guided tour of beautiful homes and gardens throughout Old Town Alexandria. We’re also proud to have three of our agents - Babs Beckwith, Lauren Bishop, and Lisa Groover - sponsoring this wonderful community tradition.
Tickets | If there is inclement weather, the homes tour will take place September 27
Clarendon Day | September 26
Join us for live music, delicious food, local art, and family-friendly fun at Clarendon Day - one of Arlington’s most popular street festivals. We will be there as an exhibitor, so be sure to stop by our booth and say hello!
Free Admission
Leesburg Airshow | September 26
Leesburg Executive Airport, Leesburg
The skies above Leesburg come alive with skydiving and aerobatic performances, while on the ground exhibitors showcase unique aircraft and general aviation. With activities for the kids, food and beverages, it’s fun for the whole family. You also don’t want to miss the aerial performances that begin at 1 p.m.!
Free Admission
WEST VIRGINIA
Charles Town Car Show | September 5
101 E Washington Street, Charles Town
Check out the biggest car show in the region located in downtown Charles Town. All makes and models! Want to have your car in the show? Register here!
Trace Adkins: 30th Anniversary Tour | September 19
Hollywood Casino at Charles Town Races, Charles Town, WV
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The Mountain Heritage Arts and Crafts Festival | September 25-27
Jefferson County WV Fairgrounds
The Jefferson County Chamber of Commerce cordially invites you to celebrate the 50th anniversary celebration of this year’s festival at Jefferson County WV Fairgrounds in the rolling countryside. Stroll among the tents, buildings, and pavilions as you admire the many crafts, fine arts, and wine.
Tickets | Children under 13 are free
