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Back to school and back to the office doesn’t mean the end of fun activities with family and friends. September is the beginning of fall festival season showcasing food and drink, music, crafts, and much more. Check out our top selections for September events around DC, Maryland, Virginia, and West Virginia.
WASHINGTON, DC
Photo courtesy of DC Bike Ride
NSO Annual Labor Day Concert | September 1
The National Symphony Orchestra’s annual Labor Day weekend concert returns to the West Lawn of the U.S. Capitol! This year, the NSO performs classics by Duke Ellington, George Gershwin, John Philip Sousa, Wolfgang Amadeus Mozart, and more led by charismatic conductor Enrico Lopez-Yañez and featuring Grammy–nominated rapper/beatboxer Christylez Bacon. A must-see celebration! Seating is first-come, first served.
Free Admission
DC Bike Ride | September 6
Intersection of 12th St. NW and Constitution Ave. NW
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
Enjoy a free showcase of the District’s agricultural, culinary and creative talents with a daylong celebration of all things homegrown. Inspired by time-honored state fair traditions, growing and gardening, contests and delicious foods, the DC State Fair honors what makes the nation’s capital one of a kind. Some past activities have included: competitions for best photographer, best mumbo sauce, the most creative use of space in a micro-garden, slime for kids and much, much more.
National Gallery Nights | September 11
National Gallery of Art, East Building
One of the city’s most popular museums hosts this after-hours extravaganza that uses a lottery system to handle the high demand. Expect the East Building of the National Gallery of Art to be decked out in Back to School style, with activities that bring to mind the excitement of the first day of the new school year.
Passes are available at the East Building entrance—first come, first served
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 26-28
10475 Little Patuxent PkwyColumbia, 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, an epic lineup of delicious local eats and art installations.
MARYLAND
Photo courtesy of Bay Bridge Paddle
The Great Frederick Fair | September 12-20
Frederick Fairgrounds
This annual fair includes a carnival midway, nightly grandstand entertainment, international award-winning agricultural exhibits, activities, and of course fantastic food!
Bay Bridge Paddle | September 13 & 14
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.
VIRGINIA
Photo Courtesy of The Bluemont Fair
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 6
Gateway Park
Arlington, Virginia’s most popular free outdoor music festival returns Saturday the 7th at Gateway Park! Join the Rosslyn BID and Arlington Arts at the 33rd 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 10
River Creek Country Club
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.
Falls Church Festival | September 13
Community Center
This family-fun event features The Taste of Falls Church, a beer garden, live music, children’s entertainment, and booths from local crafters, businesses, and civic organizations.
Free Admission
Mount Vernon Colonial Market & Fair | September 13 & 14
Mount Vernon Estate
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 19
Town Green, Vienna
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 20 & 21
Bluemont
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
83rd Historic Alexandria Homes Tour | September 27
106 N Columbus St, Alexandria
Since 1997, The Twig has hosted this annual event offering a self-guided walking tour of beautiful homes and gardens in Old Town Alexandria.
Clarendon Day | September 27
Clarendon Metro Park
Join us for music, food, art, and fun for the whole family at this year’s Clarendon Day – one of Arlington’s most loved street festivals. Stop by our table and say hello!
Free Admission
Leesburg Airshow | September 27
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.
Free Admission
WEST VIRGINIA
Photo courtesy of Mountain Heritage Arts & Crafts Festivals
Kenny G | September 5
Hollywood Casino at Charles Town Races, Charles Town, WV
Kenny G, whose real name is Kenneth Bruce Gorelick, is a smooth jazz saxophonist, composer, and record producer. He’s known for his instrumental versions of pop hits like “My Heart Will Go On” and “Careless Whisper”.
The Mountain Heritage Arts and Crafts Festival | September 26-28
Jefferson County WV Fairgrounds
The Jefferson County Chamber of Commerce cordially invites you to 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
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